Tag: Features

I was on the phone with a friend Sunday night discussing the weekend’s onslaught of Drake and Kendrick Lamar songs when he abruptly cut me off. “Kendrick … I mean Drake—Drake just dropped,” he said, correcting himself and unintentionally capturing the whirlwind nature of this feud. The last great rap beef had settled into the rhythm of an avalanche the past week: Kendrick drops two songs, then Drake drops, then Kendrick drops two more. You may have stepped into a movie thinking Drake had the upper hand, but if you checked Twitter right after the credits rolled, you may have thought his career was over. We’ve come a long way since the days of Jay-Z and Nas, when they fired six shots back and forth over 18 months. By comparison, Drake and Kendrick dropped a combined six records in six days.

But admit it: Despite the breakneck pace—and setting aside some of the ickiness of the songs—this was the most fun rap had been in years. Which makes sense, because hip-hop has always been built on competition: graffiti artists writing over each other’s work, DJs squaring off with scratching and beat-juggling routines, breakdance crews facing off on cardboard. And that’s even before getting to the MCs—arguably the most egotistical of the bunch, and definitely the best suited to destroy any challengers given the nature of their craft. That battle element is embedded in mostly everyone who’s ever picked up a mic: From Kool Moe Dee and Busy Bee to Nicki Minaj and Megan Thee Stallion. At times, it’s turned violent—some of the beefs on this list did not stay on wax—and at others, it’s gone Hollywood—Eminem’s most famous moments may have come courtesy 8 Mile—but it’s never gone away.

What we’ve been witnessing with Kendrick and Drake (and Rick Ross, and Metro Boomin, and …) is among the greatest rap beefs ever. When you consider the scale of the artists involved and the speed at which social media moves, it’s almost certainly the biggest ever. There’s a spectacle to this that’s gone beyond punchlines: the memes, the livestreams, and anticipation have made this probably the biggest cultural event of the year. (Put it this way: Do you even remember when Taylor Swift and Beyoncé dropped sprawling albums just a few weeks ago?)

We here at The Ringer are ready to call this thing over. There may be other tracks in the Kendrick-Drake feud—hell, one could drop right after this list publishes—but unless something wild happens outside the music, there’s a clear winner. (Who it is will be revealed as you read on.) But we wanted to take a moment to not only mark this beef, but also all the consequential beefs that have happened in rap’s long and storied history. And that’s why we present to you the 81 greatest diss records in hip-hop history, ranked as definitively as we can.

Before we get to the list, a couple of things to note. First, we wanted to step back and see which feud is most represented in this ranking. And well, maybe we’re slight prisoners of the moment.

Drake vs. Kendrick (plus Rick Ross!) produced the most songs on this ranking. But right behind it came the other most storied beefs in hip-hop’s annals: Jay-Z vs. Nas with five (the only song missing was Nas’s “Last Real N—a Alive,” an excellent track that’s more of a retelling of events than a diss), and the East Coast vs. West Coast feud of the mid-’90s. (While we here at The Ringer recognize it was mostly a media construction—and probably more a Death Row vs. Bad Boy affair—groups like Mobb Deep and Capone-N-Noreaga are integral to that part of history.) Coming right behind it are the Juice Crew–vs.–Boogie Down Productions Bridge Wars, LL Cool J. vs. Kool Moe Dee, and the long, public dissolution of N.W.A. (Also worth noting: Plenty of beefs on this list had two entries, but it takes a special kind of vitriol to land more than that.)

But since we’re acknowledging a slight bit of recency bias, we also wanted to tally which decade had the most tracks on the list. And well …

The ’90s runs away with this. You can assume we’re old heads, but also let’s acknowledge that it was a special time: when rap was maturing commercially, giving many of these records widespread distribution and MTV and BET play, but also coming at a time when the genre was still relatively young, meaning the artists still felt free to let the unbridled hate fly.

Lastly, before we begin the list, we wanted to run through some honorable mentions that didn’t make the cut:

• “Officer Down,” Lloyd Banks: Banks in peak battle mode. Still, it’s truly amazing that Rick Ross was outed as a correctional officer and came out relatively unscathed. Maybe he is the Teflon Don.
• Rick Ross’s Instagram: Speaking of Rozay, our dude just made both #bbldrizzy and private-jet flight safety national concerns. If there’s any lesson from this current sprawling feud, it’s don’t mess with someone funnier than you.
• “H.A.A.,” Black Sheep: Or, “Here’s Another Asshole.” Lots of people dissed MC Hammer in the ’90s, but Dres and Mister Lawnge hated this guy.
• “One Day,” Jeru the Damaja: See also: “What They Do” by the Roots. Dissing shiny-suit rappers in general—and Big and Puff specifically—was a cottage industry in 1996-97. No one went at it harder than the Black Prophet.
• “Ova,” Jaz-O / “Get High (Freestyle),” Roc-A-Fella Records: The best rap bad blood goes back decades. In this case, it goes back to the “Hawaiian Sophie” days.
• “Drop That Soulja Rag,” Da Wild Boyz: “Juvenile!!! Step away from the Hummer!!!” A great New Orleans rap beef that’s been forgotten to time.
• “Go to Sleep,” Eminem, DMX, Obie Trice / “Hail Mary,” Eminem, 50 Cent, Busta Rhymes: At some point, you just gotta leave Ja Rule alone.
• “Crook County,” Twista featuring Speedknot Mobstaz: As list contributor Andrew Barber reminds me, all the Midwest fast rappers were beefing at the time.
• “Faneto,” Chief Keef: No one has done this much damage to New Jersey’s reputation since the Situation.
• “Obsessed,” Mariah Carey: I was tempted to sneak this on the list before a colleague said it was the “Die Hard is a Christmas movie” argument in rap form. Still, you know it’s good because people on r/Eminem hate it.

Without further ado, here are the 81 greatest diss tracks in hip-hop history—plus a few dishonorable mentions. (And be sure to check out our Spotify playlist of many of the songs on this list here.) —Justin Sayles

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81. “Champagne Moments,” Rick Ross

Year: 2024

Target: Drake

What’s the most vicious part of this song? Sometimes the most vicious and iconic portion of a diss record isn’t the raps, it’s the monologue on the outro. “Champagne Moments” is one of those tracks. To be quite honest, I could’ve done without the raps and instead got a double helping of Ricky Ross talking shit about Drake over the luxurious Mini Boom and Trop–produced beat.

Somehow, as a Black person, the only thing that stings nearly as bad as being called a racial slur is being called a white boy. It’s a schoolyard-level insult used to shame Black kids into feeling like outsiders to their own race for talking a certain way or doing stuff that a white person is expected to do. And if that Black person is insecure about their Blackness, it’ll sting. Every time Ross says “white boy” in the outro, it feels like a grenade thrown at the “mob ties” persona Drake has donned for the past few years. (It’s also a form of precognition for Drake responding to the record in the whitest fashion possible: by telling his white mother that Rick Ross is racist for calling him white.) And to top it all off, Ross exposes Drake’s plastic surgery–made abs.

What’s this song’s legacy? “Champagne Moments” will be remembered as the war on Drake’s Battle of Bunker Hill or D-Day. It immediately softened the blow of Drake’s diss “Push Ups”—which leaked the same day—it gave the anti-Drake brigade reinforcements while stalling for Kendrick Lamar’s eventual response, and most importantly, it reminded everyone where Drake is most vulnerable by once again putting Drake’s insecurity as a Black man back on trial for the world to see. Oh, and it was funny as hell.

Who caught the worst stray? White boys that wear Dockers without underwear. Do y’all really do that shit? —Jonathan Kermah

80. “Pussy Ass Kid and Hoe Ass Play (Payback Is a Mutha Fucker),” Luke featuring JT Money and Bust Down

Year: 1992

Target: Kid ‘N Play

What’s the most vicious part of this song? Honestly, this song makes the cut based on its title alone. But Uncle Luke letting his henchmen ride on the House Party boys with lines like “You got a flat top thicker than commodity cheese” and “If I see you at a show and you’re slippin’, you’re gettin’ pissed on” was a chess move that Kid ‘N Play couldn’t begin to kick-step their way out of.

What’s this song’s legacy? As legend has it, Luke saw Salt-N-Pepa on BET with Kid ‘N Play talking about how they didn’t like 2 Live Crew’s, uh, provocative lyrics. And if we know anything about Luke, it’s that he’s going to defend his group’s content—whether that’s in court or against a couple of rapping actors. Luke remains a legend. Kid ‘N Play, meanwhile, haven’t made an album since this song dropped, but you can catch them in Progressive commercials.

Was this song a knockout blow? In 2020, Kid told DJ Vlad that when he and Play saw the song title, they knew they had to tap out. “We barely cursed,” he laughed. He may be selling his group short: “Darn Luke” could have gone off. —Justin Sayles

79. “Quiet Storm (Remix),” Mobb Deep featuring Lil’ Kim

Year: 1998

Target: Charli Baltimore

What’s the most vicious part of this song? “I’m a leader, y’all on some followin’ shit / Comin’ in the game on some modeling shit / Bitches suck cock just to get to the top / I put 100 percent in every line I drop.”

The “10% Dis” nod at the beginning of Lil’ Kim’s verse is a canny historical reference that makes her intentions clear from the jump. But it’s the disdain in her voice, and how well it gels with Havoc and Jonathan Williams’s sinister production, that resonates the deepest as she flexes her bona fides while dismissing the target of her insults. (More on that later.)

What’s this song’s legacy? The origin of “Quiet Storm” can be traced back to 1997, when Prodigy recorded a rough cut that DJ Clue got his hands on. Within two years, a polished version became the lead single for Murda Muzik, Mobb Deep’s perfect balance of commercial success and the ominous street rap on which Prodigy and Havoc hung their bandanas.

But the “Quiet Storm” remix was Lil’ Kim’s showcase—a perfect exhibition for the intonation, presence, and pure venom that made her more than a provocateur. “Quiet Storm” was already a major, if not unlikely, club hit at places like The Tunnel by 1999. Lil’ Kim elevated the remix off the strength of her presence alone, all while using the moment to air out a rival who, let her tell it, was just an imitator.

What’s your favorite behind-the-scenes thing about this song? How people thought Lil’ Kim’s verse was about Foxy Brown (who she later feuded with) when she was actually sniping at Charli Baltimore. —Julian Kimble

78. “U Ain’t Bone,” Bone Thugs-N-Harmony

Year: 1997

Target: Three 6 Mafia, Do or Die, other Midwest fast rappers

What’s the most vicious part of this song? When Layzie Bone said, “N—-s gonna pay on the day that I spot him / Toss him in the trunk of the Caddy / on the way to the rodeo, killing all carbon copies.”

The irrationally territorial state of hip-hop in the mid-to-late 1990s wasn’t just about regions on a map; it was also about signature styles. Bone didn’t have a dog in the East vs. West Coast fight—although the Cleveland-bred group has a footnote in rap’s most infamous beef because it recorded tracks with 2Pac (“Thug Luv”) and Biggie (“Notorious Thugs”) before they died—but Bone did have its own intra-Midwest battle with Chicago-based groups Crucial Conflict and Do or Die. Their beef wasn’t over land, but rather the idea that, basically, anyone who rapped fast was copying Bone. The three groups were otherwise completely different: Crucial Conflict had a cowboy/farmer aesthetic, Do or Die embraced the pimp/playa look, and Bone was Ouija boards and funeral vibes. But for its 1997 album, The Art of War, the thuggish ruggish group went military style, taking up arms against “clones” trying to be like Bone. Layzie’s line about Cadillacs and rodeos was an obvious shot at the Chi-town pimps and farmers—about as clear and articulate as it got for a Bone track at the time.

What’s this song’s legacy? “U Ain’t Bone” is the most direct and dedicated diss track, but really, The Art of War is a diss album. (A diss double album, at that.) From “Ready 4 War” (Bizzy Bone: “Fuck you, you weren’t original / Mano a mano ain’t no subliminal”) to “Look Into My Eyes” (Layzie: “Harmony smooth with the thug shit, mo’ murda to the fools that clone”) and several others, they emptied the clip on any real or perceived rivals.

This is also the rare Bone track for which it felt necessary to pay close attention to the actual words coming out of their mouths (no matter how many stop-and-rewinds it took), instead of just humming and scatting in harmony as usual.

Was Bone punching up or down—and does that matter? This felt like hip-hop Whac-A-Mole. Bone was on top of the industry for the latter part of the 1990s, while acts like Crucial Conflict and Do or Die were just trying to get their foot in the door and make a mark. And the Thugs-N-Harmony weren’t letting that happen on their watch. Twista, the Usain Bolt of rapping fast, and Three 6 Mafia, whose themes of death and darkness flew too close to Bone for their liking, were also targeted on disses like “U Ain’t Bone.” Whoever popped up on the scene looking or sounding like a clone, Bone knocked ’em down. —Amaar Burton

77. “The Book of Daniel,” MF Grimm featuring MF Mez and Bashton the Invizabul Mang

Year: 2006

Target: MF Doom

What’s the most vicious part of the song? What makes “The Book of Daniel” cut deep is that this isn’t two rappers vying for women or who’s the best; this is two brothers having a very real disagreement with each other, with one of them pulling back the curtain to expose what fans were never privy to. It’s the disillusion of a friendship more than it is a diss song. Grimm sounds conflicted, though; while he’s down to mention every name he says helped Zev Love X become MF Doom, he also acknowledges that he never should have made any private money issues he had with Doom public. Although part of that was because Grimm and his associates felt that Doom was taking shots at them. “But now you’re being disrespectful to me and the crew,” Grimm raps toward the beginning of his third verse. “Now I gotta do what I gotta do.”

What’s this song’s legacy? This track’s legacy is tricky; we fully understand that there are casual rap fans who have probably never heard this song before (or aren’t aware of much of Grimm’s catalog). But for those who follow the underground, “The Book of Daniel” highlights Grimm’s talents as an emcee while giving fans a peek into the creation of one of hip-hop’s most illustrious figures.

Was MF Grimm punching up or down—and does that matter? Up. “The Book of Daniel” is meant to be a cautionary tale for up-and-coming rappers about what can happen when friendship and business start to mix. —Jayson Buford

76. “Shots Fired,” Megan Thee Stallion

Year: 2020

Target: Tory Lanez

What’s the most vicious part of this song? “I told him, ‘You’re not poppin’, you just on the remix’”—because any time you can accuse someone as risible as Tory Lanez of riding Jack Harlow’s coattails, you gotta take it.

What’s this song’s legacy? Before the legal system doled out its punishment, “Shots Fired” served as Meg’s revenge for the July 2020 incident in which Lanez shot her in the foot. That it comes over a beat that flips the same sample as “Who Shot Ya?” places it in a lineage of great, aggressive rap songs—though unlike Biggie’s track, there’s no mistaking who “Shots Fired” is about.

Who caught the worst stray? Kelsey Nicole, Meg’s former friend who the rapper suggests may have taken hush money to keep quiet about the incident. With friends like that, who needs wannabe tough guy Canadian singers? —Sayles

75. “Get At Me Dog,” DMX

Year: 1998

Target: K-Solo

What’s the most vicious part of this song? “Up north, this n—- never made a sound”

What’s this song’s legacy? It starts in prison a decade earlier, where DMX and EPMD affiliate K-Solo were both serving time. During their stints, they occasionally rap-battled and developed a general distaste for each other. A few years later, after both men were released, K-Solo scored minor hits with the songs “Spellbound” and “Letterman” where he’d, well, use letters to spell things. X claimed Solo bit this style from him and released his own version. That was in 1991. Seven years later, when X scored his first major record deal, he used his debut single to once again take shots. As a diss, it’s lukewarm. As a song, it’s as hot as hell. It sent X’s career into the stratosphere, eons beyond where Solo’s stalled out. And not even the threat of a boxing match could change that.

What’s your favorite behind-the-scenes thing about this song? In EPMD’s “Knick Knack Patty Whack,” Solo misspelled bird as “B-R-I-D.” Surprised X didn’t sic his D-G-O-S on him for that. —Sayles

74. “Push Ups,” Drake

Year: 2024

Target: Kendrick Lamar, Future, Metro Boomin, Rick Ross, the Weeknd, the Weeknd’s manager, Ja Morant

What’s the most vicious part of this song? I went through the lyrics tonight, and the best thing I could come up with is Drake’s “shut up and make some drums” line, which is less of a bar and more of an imperative one-off statement. The memes directed at Metro Boomin that followed were elite, but as far as diss tracks go, “Push Ups” cast a wide net and hit its targets with glancing blows rather than knockout punches. In theory, there’s nothing wrong with that. But considering the guerilla warfare that ensued in the form of Kendrick’s Drake-hating magnum opus, “Push Ups” could’ve used a few more specific, scathing bars.

What’s this song’s legacy? In the immediate aftermath of its release, “Push Ups” looked like a solid first response to Kendrick’s slights in “Like That.” Drake got shots off at most of his enemies and saved a few more personal bars (“your last one bricked, you really not on shit”) for his main target. But in the wake of Kendrick’s subsequent full-on assault—which included “Euphoria,” “6:16 in LA,” “Meet the Grahams,” and “Not Like Us”—“Push Ups” is more likely to be remembered as a mistake than one of Drizzy’s stronger battle moments.

Who caught the worst stray? I’m going to flip this question on its head a bit and say SZA. Nearly everyone Drake dissed—from Kendrick to Rick Ross to the Weeknd—had it coming. But the people Drake shouted out when dissing Kendrick (“SZA got you wiped down / Savage got you wiped down”) deserved better. For her part, SZA responded to Drake’s complimentary name-drop by posting the NeNe Leakes “now why am I in this” meme on Instagram.

Who could blame her? Though Drake was effectively issuing SZA a public compliment, she’d have been better off not being associated with the losing team of this very one-sided rap battle. In retrospect, we all owe J. Cole an apology: Steering clear of this messy, rap-history-altering feud would’ve been the best move for everyone involved not named Kendrick. —Daniel Comer

73. “T-Shirts Buddens,” Lil B

Year: 2010

Target: Joe Budden

What’s the most vicious part of this song? With all due respect to Lil B’s incredulity that Joe Budden would speak ill of him even though Budden has “a fucking full beard,” it has to be “Shut the fuck up with those depressin’-ass songs / It’s the summertime—get some fuckin’ pussy and go home.”

What’s this song’s legacy? That would be The Joe Budden Podcast. Lil B didn’t quite end Budden’s rapping career, but the diss coincided with Budden’s slide out of rapper’s-rapper cult hero status and into drive-time punditry; that the diss is by such an internet denizen makes the story all too tidy.

Was Lil B punching up or down—and does that matter? The best part about this beef is that I’m absolutely positive each of them had Wikipedia open while trying to craft insults about the other. —Paul Thompson

72. “Wack 2 Wack,” Sauce Walka

Year: 2015

Target: Drake

What was the most vicious part of this song? Sauce Walka attacking Drake for the one thing he’ll never have: authenticity. “You been wanting to be a rapper but that shit was wack,” Sauce raps over Drake’s own “Back to Back” beat. “Dropped some songs that didn’t work so you had to act / Nickelodeon-ass n—a, coachin’-ass n—a / You ain’t Black, you a fucking Cambodian-ass n—a.”

In the same way that Kendrick Lamar is doing now, Sauce Walka was taking Drake’s manufactured superstardom to task. The Toronto rapper and pop behemoth has dabbled in the flows and slang of Houston rap, Atlanta rap, Memphis rap, London drill rap, and even SoundCloud rap. At his core, Drake is the kid from Degrassi who tried on new outfits and decided which one fit him the best. Authenticity is not his strong suit—it’s something he abandoned to play a character, both as an actor and off the camera. In the music world, it’s what’s made him a dominant force. In a rap beef, it makes him vulnerable against these street dudes, who could never even imagine switching up their personas.

What’s this song’s legacy? Sauce Walka opened up a hole in Drake’s identity, which allowed other rappers to pick up on Drake’s fatal flaw. He belongs to no code, other than his own need for success. It’s what hurt him in his beef with Kendrick. Drake is toast; Sauce started that energy.

Was this song a knockout blow? Sauce Walka was not famous enough to dent Drake’s armor, and Aubrey looked nearly untouchable at the time. Drake never responded to this, and “Wack 2 Wack” became a footnote in the beef with Meek Mill, which Drake won with ease. —Buford

71. “Paper Plate,” GZA

Year: 2008

Target: 50 Cent

What’s the most vicious part of the song? Midway through the second verse, GZA rips off a heater: “You ain’t nothing but a pig in a blanket / Hoghead, the deadliest food at the banquet / All this rap crap that’s trapped in your colon / only means, get rid of the wack shit you’re holdin’.” Harsh words toward 50 Cent, who Wu-Tang have had a beef with ever since 50 named ODB, Rae, Ghost, and RZA on “How to Rob.”

What’s this song’s legacy? 50 Cent is rich; you and I, not as much. The guys who catch him slipping might not be as famous as he is, but they are certainly more respected in the streets. This song is another paradox of 50: that all the money in the world can’t garner him respect.

What’s your favorite behind-the-scenes thing about this song? Although 50 did have beef with Wu-Tang because of his song “How to Rob,” this specific beef with GZA started with GZA dissing Soulja Boy and 50 quickly coming to Soulja’s defense. It’s funny that someone as seemingly inconsequential to New York rap can start a beef. —Buford

70. “Drag ‘Em N Tha River,” U.N.L.V.

Year: 1996

Target: Mystikal, Big Boy Records

What’s the most vicious part of this song? “You fake cheerleadin’ bitch” are the first words you hear when the Mannie Fresh beat fires up. The line was in reference to Mystikal’s days as a well-known high school cheerleader in New Orleans.

What’s this song’s legacy? Mystikal was one of, if not the first, New Orleans rapper to break out nationally. In 1995, Jive Records released his first nationally-distributed album, Mind of Mystikal, which included the single “Y’all Ain’t Ready Yet.” The video garnered national airplay on shows like Yo! MTV Raps and Rap City, but most people outside the Bayou had no idea the song included a subliminal diss aimed at a local group by the name of U.N.L.V: “One never gonna change my style, never gonna bounce, never gonna bow.”

The sub was in reference to “Eddie Bow,” a New Orleans bounce hit by U.N.L.V.—one of the first acts signed to Cash Money Records. Not taking the diss lightly, U.N.L.V. quickly fired back with “Drag ‘Em N Tha River,” a scathing diss track poking fun at Mystikal’s hairstyle and his days as a high school cheerleader. The song became a local anthem and quickly spread around the region and then the country, helping to expand Cash Money’s reach.

Was this song a knockout blow? No. Mystikal was on his way to becoming a nationally known star and would later sign with the red-hot No Limit Records in 1996. U.N.L.V. unfortunately lost their momentum after leaving Cash Money and then suffered the tragic murder of group member Yella Boy in 1997. On the mic, Mystikal did get his lick back with “Let’s Get Em” from Master P’s multi-platinum Ghetto D album, unloading a whole clip on U.N.L.V. in his high-energy verse (“I take a braid out my own head, whoop yo’ ass with one of my plaits”).

What’s your favorite behind-the-scenes thing about this song? Fifteen years later, Mystikal would sign to Cash Money Records—a move that shocked longtime supporters and No Limit loyalists. And while this partnership failed to produce an album, it was interesting to see Mystikal join forces with the label he was once at odds with (and was at odds with his previous two label homes: Big Boy and No Limit). It never felt right and that’s perhaps why it didn’t work out. —Andrew Barber

69. “Big Shot,” Joe Budden

Year: 2004

Target: 50 Cent, the Game, Young Buck

What’s the most vicious part of this song? In hindsight, it’s probably Budden mocking the kind of jail time 50 did, as a few years later 50 would try to make the incongruity between Rick Ross’s resume and his on-record persona the silver bullet in their own battle. But at the time, it was locating the Game, perpetually on the coattails of more interesting artists: “When you see him, he just dancing in the background.”

What’s this song’s legacy? At this point Joe Budden is far, far more famous than his catalog, perhaps even including “Pump It Up,” and though 50 has receded into TV moguldom (and Game into the depths of The Shade Room), you’d be hard-pressed to say Budden specifically was vindicated. Maybe it survives as a reminder to mine the depths of early reality TV.

Who caught the worst stray? “And as far as Banks and Buck, I’m done discussing ‘em / I only beef with n—-s who own publishing.” —Thompson

68. “Never Personal (Fuck Nature and Nas),” Cormega featuring Delorean

Year: 1998

Target: Nas, Nature

What’s the most vicious part of this song? “That’s why my man took your fuckin gold chain / And he’s wearin’ your shit in the projects, you’re a fuckin bitch / Namsayin, Nas? You need to you need to you need to / Get a fuckin fireproof fuckin’ van next time you come through.”

What’s this song’s legacy? Hell hath no fury like a crew member scorned. Cormega was the secret weapon of the Firm—the Nas, AZ, and Foxy Brown supergroup that debuted on It Was Written’s “Affirmative Action.” But things eventually went sour between Mega and the QB clique’s leader—reportedly over shady label mechanics and disagreements with Nas’s manager, Steve Stoute. Cormega was summarily replaced with Nature—a childhood friend of Nas and a C-minus knockoff of Mega. (Something Mega acknowledges on this track: “Yo, who this fake n—a soundin’ like me? / You wanna be me, but can’t see a thousand like me.”) The Firm would go on to put out an album with Nature produced by Dr. Dre in 1997. But “Never Personal”—whose beat bears an uncanny resemblance to “Shook Ones”—quickly became a college-radio staple the next year and remains the best thing to come out of this beef. But Mega may have not even needed it because, as Dre famously acknowledged, “the Firm flopped.”

Was Cormega punching up or down—and does that matter? Against Nas: way up. Against Nature: way down. (Though shout-out to the “Ultimate High” beat.) —Sayles

67. “Acknowledge,” Masta Ace

Year: 2001

Target: The High & the Mighty, Boogieman

What’s the most vicious part of this song? “One thing: Who named y’all the High and the Mighty? / To me, y’all just sound like a couple of high whities”

What’s this song’s legacy? That a misunderstanding can lead to a classic diss song. The legend is the High & the Mighty—the Philly duo who put a minor indie-rap classic on Rawkus Records in 1999—mentioned Masta Ace and his Slaughtahouse crew onstage at the annual CMJ conference. But it wasn’t supposed to be a diss: Ace was told in a game of telephone that rapper Mr. Eon said, “fuck Masta Ace and fuck the Slaughtahouse,” when in reality, he said, “pumpin’ Masta Ace, I walk into a Jewish slaughterhouse.” (Yikes.) Still, before the misunderstanding was cleared up, Ace released “Acknowledge,” a standout on his 2001 album, Disposable Arts. As for the song’s other target—Boogieman, who actually did diss Ace—well, turns out he was as real as the tooth fairy.

Was Masta Ace punching up or down—and does that matter? Considering Ace was on “The Symphony” and the High & the Mighty were on the Rawkus JV team, way down. But “Acknowledge” did help revitalize Ace’s career at a time when he needed it. —Sayles

66. “No Mo Play in GA,” Pastor Troy

Year: 2001

Target: Master P

What’s the most vicious part of this song? The intro mocks the beginning of Master P’s biggest hit, “Make ’Em Say Uhh!” with Pastor Troy ringing the offices of “No Limit Studios” inviting the No Limit Soldiers to battle: “Since everybody think they soldiers / Then what’s up, we’ll go to war.”

What’s this song’s legacy? No Limit Records was on top of the world in the late ’90s, thanks to a stable of artists that included Master P, Snoop Dogg, Silkk The Shocker, and Mystikal. The Louisiana-based independent label seemingly churned out gold and platinum albums weekly and dominated radio, video, and Billboard charts—not to mention they had movies in theaters, toys in stores, and their CEO auditioning for the NBA.

But as the ’90s came to a close, adversaries began taking aim at the colonel and his soldiers, hoping to send the golden tank offtrack. While many subliminals were fired their way, it was Georgia boy Pastor Troy who called them out by name and turned a diss record into a certified Atlanta anthem.

Was this song a knockout blow? No. However, the tank was starting to run out of gas and Pastor Troy pounced at the right moment. The No Limit empire crumbled shortly thereafter, with most soldiers defecting and going AWOL—but “No Mo Play in GA” had nothing to do with that. It did, however, cool Master P down in Atlanta, one of his biggest markets.

What’s your favorite behind-the-scenes thing about this song? Hot 107.9’s Birthday Bash concert is one of Atlanta’s most important annual events and a summertime staple. “No Mo Play in GA” was so scorching hot in 1999, the station had no choice but to offer Troy a headlining slot on the bill. However, when Master P got word of Pastor Troy’s inclusion, he phoned the station and offered to headline the Bash for free if they removed Troy from the lineup. The station obliged and the Pastor was dropped—or so they thought.

Fellow ATLiens Goodie Mob came to Troy’s rescue and brought him out as a special guest during their set, and he absolutely stole the show and brought the house down. Troy has claimed in many interviews that you could hear the “We Ready” chants two miles away. “We hit that stage. That shit was viral before viral,” Troy told the Big Facts podcast. —Barber

65. “Linda Tripp,” El-P

Year: 1999

Target: Sole

What’s the most vicious part of this song? [Sole’s voice chopped out from a recorded phone call]: “I-I-I-I love Company Flow … I wanna be down.”

What’s this song’s legacy? Look: To fully explain this one, we’d have to break out the Jansports and head to an open mic night in cow country. But way back, decades before El-P teamed up with Killer Mike for Run the Jewels, he was in a group named Company Flow that had beef with a rapper from Maine named Sole. El and Sole tried patching things up on a phone call, but when that failed, Sole’s own words became the coffin he was buried alive in. The message boards went nuts for this one.

What’s your favorite behind-the-scenes thing about this song? Probably that it sampled Bjork, of all people. My guess is she would’ve fucked with a few Anticon releases, though. —Sayles

64. “Kill That Noise,” MC Shan

Year: 1987

Target: Boogie Down Productions

What’s the most vicious part of this song? Shan repeatedly calling KRS-One dumb for misunderstanding “The Bridge.” But even that ignores the reality that the Blastmaster likely willfully misread that song—and it only highlights why Shan lost.

What’s this song’s legacy? It’s a relatively tame affair that’s still significant because it was Shan’s most high-profile response in the Bridge Wars. But the song also took on a tragic tone shortly after its release when BDP’s Scott La Rock was killed in an unrelated incident—with the same type of pistol Shan shouted out in this record.

Was this song a knockout blow? Nope. These days, it’s little more than a footnote. When I hear this song today, I hear a style of rap that wouldn’t exist much longer: the heavy-reverb vocals, the short sample chops over bare-bones drums. It’s a style that defined the genre in its infancy, but it’s one that was basically wiped out within a few years—partly thanks to “The Bridge Is Over.” —Sayles

63. “Stomp (Remix),” Young Buck featuring Ludacris and the Game

Year: 2004

Target: T.I.

What’s the most vicious part of this song? It’s undoubtedly the long crescendo to the end of Luda’s verse—the mounting dread in the beat, and underlying sense that some subliminal animosity is going to become less so—that pays off with: “Nobody’s thinking ‘bout you, plus your beef ain’t legit / So please, stay off the T.I.P. of my dick.”

What’s this song’s legacy? Musically, the DJ Paul and Juicy J beat is one of the most interesting things to come out in 2004, a bridge between the horrorcore edge Three 6 Mafia spent years whetting, the crunk music rattling club speakers at the time, and the more staid DJ Toomp maximalism that was about to take over radio. As for the beef, though …

What’s your favorite behind-the-scenes thing about this song? An important thing to know about me is that I bought Straight Outta Cashville the Tuesday it came out. Which means that my CD copy had a sticker affixed to its liner, under the jewel case, updating the credits to read “12. STOMP F/ THE GAME & LUDACRIS.” The T.I.-Ludacris feud stemmed, like so many in rap history, from a misunderstanding—an ambiguous t-shirt flashed for a second in a video—but very nearly played out on a single track of a retail release. T.I. originally laid a verse for “Stomp” and included a line with a play on Ludacris’s name, his response to the perceived slight in I-20’s “Fighting in the Club” video. But after Buck played the song for Luda, the latter insisted he get on the record, and Buck ended up swapping Tip for Game, who stumbles through a characteristic clot of proper nouns. —Thompson

62. “Stay Schemin,” Rick Ross featuring Drake and French Montana

Year: 2012

Target: Common

What’s the most vicious part of this song? Like most diss records, the defining (and catchiest) moment of “Stay Schemin” is also what’s aged like a banana in the hot bodega sun. After dismantling Common and daydreaming about spaghetti bolognese, Drake circles the block to cosplay as Kobe Bryant’s divorce attorney as he yelps from the arbitration room, “Bitch, you wasn’t with me shootin’ in the gym!” It doesn’t help that seconds later, Ross arrives with his patented grunt to repeat Drake’s call-to-arms like a sweaty deacon in the world’s most misogynistic church. Drake and Common squabbling over who deserved to be with Serena more (spoiler alert: neither), devolving into Aubrey sending shots at an unrelated woman because she didn’t log enough hours at Planet Fitness with her husband is the encapsulation of how most beefs with the Canadian go.

What’s this song’s legacy? Remember when music publications still existed and writers would get paid meager sums to obsess over what French Montana meant by “Fanute the coupe”?

Good, good times.

Was Drake punching up or down—and does that matter? Drake had no business beefing with Common in 2012. By that point, the legendary Chicago rapper was 40 and starring in movies with Queen Latifah. “Stay Schemin” is the equivalent of crossing up your uncle at the cookout and breaking his hip. You look like as much of the asshole as the guy you’re sending to urgent care. It also didn’t help that Common’s best retort was “You ain’t wet nobody, n—a, you Canada Dry.” —Charles Holmes

61. “Piggy Bank,” 50 Cent

Year: 2005

Target: Ja Rule, Fat Joe, Jadakiss

What’s the most vicious part of this song? The line that’s always been the most hilarious and cruel in “Piggy Bank” isn’t even addressed at Ja Rule. At this point in their beef, Ja is old news, and now 50 has set his sights on anyone in New York. “Kelis said her milkshake brings all the boys to the yard, then Nas went and tattooed the bitch on his arm,” 50 says in the second verse. (Nas and Kelis have since divorced, and Kelis has accused him of domestic violence. If anyone is wondering, Nas covered the tattoo with what appears to be a lion mid-roar.)

What’s this song’s legacy? “Piggy Bank” will always be remembered as one of the only exciting moments on an otherwise lackluster sophomore album. And by exciting, I don’t mean that the disses were necessarily good or damaging—hardly anyone remembers them. What I mean is that 50 Cent always had the ability to entertain and get people talking. That’s exactly what “Piggy Bank” and its hilariously animated video did.

Who caught the worst stray? It takes a lot of courage to bring Jadakiss into a rap beef. The reason being that Jadakiss collaborated with Ja Rule on his track “New York,” which took shots at 50. “In New York n—-s like your vocals, but that’s only New York, dawg, yo’ ass is local,” 50 says. It’s a surprisingly good diss on a rapper who rarely misses. Jadakiss wouldn’t take long to respond with “Checkmate,” where he tells 50 Cent that he can’t be the king of New York when “you live in Connecticut!” —Donald Morrison

60. “Pop Goes the Weasel,” 3rd Bass

Year: 1991

Target: Vanilla Ice

What’s the most vicious part of this song? 3rd Bass sniped Vanilla Ice across their second album, Derelicts of Dialect, but to make their most extensive diss song the lead single was definitely a choice. Though Ice’s name is never explicitly mentioned on “Pop Goes the Weasel,” it’s obvious who the target is, as MC Serch and Pete Nice single him out as one more white artist who appropriates Black culture for his own commercial success. Is it hypocritical for 3rd Bass to go at Vanilla Ice for his wholescale boosting of Queen’s “Under Pressure” while using obvious samples from Peter Gabriel and the Who? Maybe, but the SD50s’s production is more artful than it may seem on first listen. Or maybe it’s meta. Or maybe it’s 3rd Bass trying to find a middle path in the debate about what’s more important in a diss song: the depth of the content or the replayability.

What’s this song’s legacy? “Pop Goes the Weasel” was another nail in the coffin for Vanilla Ice’s stardom. While he never gained widespread respect in the hip-hop community, mainstream culture was already turning on him a few months after “Ice Ice Baby” reached the top of Billboard’s Hot 100 chart. In February of 1991, Jim Carrey skewered him with the “White White Baby” parody on In Living Color. “Pop Goes the Weasel,” which was released that May, was the kick in the ass on his way out the door. The reaction to his film Cool as Ice in October was him falling off a cliff outside that door.

What’s your favorite behind-the-scenes thing about this song? Keen-eyed viewers will recognize Henry Rollins playing Vanilla Ice in the song’s music video and letting himself get whooped by the members of 3rd Blass. The clip itself was helmed by Jesse Dylan—son of Bob, brother of Jakob, and a director with such credits as the How High movie and will.i.am and his celebrity friends hyping up Obama with the “Yes We Can” songilization. And if you’re into cameos, “White White Baby” features pre-fame members of the Pharcyde as the backup dancers. —Eric Ducker

59. “Malcolm X,” Royce Da 5’9”

Year: 2003

Target: Eminem, D12

What’s the most vicious part of this song? It’s probably Royce telling Proof to be “a good little hype man” to Eminem if he wants to keep his lease, though the notion that the whole Aftermath roster was only acting tough because Suge Knight was locked up is an insight plenty of their foes must wish they had used themselves.

What’s this song’s legacy? The Eminem-Royce beef is one of the few that actually yielded more music after it was squashed. Once close friends and collaborators, the two had a falling out after Royce’s manager told Vibe that, in the sessions for Dr. Dre’s 2001—for which Royce ghostwrote the deeply personal “The Message”—Eminem would sit Dre down like a “pupil” and coach him through verses. After years at each other’s throats, though, the Detroit natives came back together for “the sequel” that was promised on 1999’s beloved “Bad Meets Evil.”

Who caught the worst stray? Kuniva, who isn’t even named alongside his D12 groupmates. “I don’t even know his name,” Royce raps, “but he can shovel my snow.” —Thompson

58. “Super Ugly,” Jay-Z

Year: 2001

Target: Nas

What was the most vicious part of this song? Hov saves his most ferocious lines for the third verse, revealing that he had been intimate with Carmen Bryan, Nas’s then-girlfriend. The filth Jay spit on wax was so, well, ugly (“I came in your Bentley backseat / skeeted in your Jeep / left condoms on your baby seat”) that Jay’s mother felt the need to call her son and tell him to apologize for going that far.

What’s this song’s legacy? Nas’s response to “Takeover,” Stillmatic’s “Ether,” found the Queens-born emcee taking on Jay-Z in a diss record so hot that its title became a verb for destroying your opps. It was a record so hot that Jay-Z was prompted to respond with two diss tracks, with the second (“Super Ugly”) pulling no punches … and getting Jay-Z in hot water with his mother.

Was this song a knockout blow? What’s the opposite of a knockout blow? Anyone who thought Nas was the victor after “Ether” didn’t take “Super Ugly” that seriously—it felt more retaliatory than anything—and many on Jay’s side were turned off by how far Hov took his pen to try and beat Nas. All may be fair in love and war, but maybe just make sure your mom can’t hear the nasty shit you’re saying about your opponent. —khal

57. “Stillmatic Freestyle,” Nas

Year: 2001

Target: Jay-Z, Roc-A-Fella Records

What’s the most vicious part of this song? “You clone me, your wack clothes line / I’d rather Sean John, bore me with your fake coke rhymes / And those times, they never took place, you liar / Un was your first court case, you had no priors.”

Jay-Z’s drug-dealer past is a significant part of his lore, so Nas called him a fraud by calling the foundation of his mythology into question.

What’s this song’s legacy? After years of tension and subliminals, “Stillmatic Freestyle” was the escalation point for one of hip-hop’s landmark feuds. This was the moment it became real: a declaration of war featuring names, accusations, and jabs for the most prominent members of Roc-A-Fella’s roster. On a deeper level, this marked the beginning of Nas’s resurgence. “Stillmatic Freestyle” may not have been the first stone cast, but it was the beginning of Nas showing that his claim to the throne wasn’t based purely on past accomplishments.

Was Nas punching up or down—and does that matter? Jay-Z was a supernova at the start of the new millennium, and while Nas was a bit adrift at the time, they were still regarded as peers. “Stillmatic Freestyle” was his hyper-focused warning shot at an opponent who he believed was undeserving of the accolades. —Kimble

56. “Shether,” Remy Ma

Year: 2017

Target: Nicki Minaj

What’s the most vicious part of this song? While Remy called Nicki to task about everything, the most personal lines were about Nicki’s brother Jelani Maraj and his charges for sexual assault of a minor (in 2020 he was convicted and sentenced to 25 years to life in prison).

What’s this song’s legacy? In promoting her calculated Nicki Minaj diss “Shether,” Remy Ma invoked one of the young characters from John Singleton’s 1991 film, Boyz n the Hood, tweeting, “You wanna see a dead body” with the link to her SoundCloud. The record, set to the instrumentals from Nas’s rap-world-shaking “Ether,” captured 10 years of Remy and Nicki’s back-and-forth through Remy’s pen.

Was this song a knockout blow? It should’ve been, but Nicki kept going. She aligned with Drake and Lil Wayne for “No Frauds,” a hit that found her laughing at Remy while doing her best to shift the narrative. —khal

55. “Long Kiss Goodnight,” the Notorious B.I.G.

Year: 1997

Target: Tupac Shakur

What’s the most vicious part of this song? It’s ill, trifling work to taunt the dead. No less so when the dirt is still fresh and your plot nearly dug. “Long Kiss Goodnight” is a tempting dance with the hereafter—flawless lyrically, abhorrent morally, and tragic, absolutely. Some things are best left unsaid; other things are said best because they shouldn’t be. In this case the song’s viciousness derives from the fact that both sentiments are true.

What’s this song’s legacy? If you can listen to this track without staining yourself with the residue of loss—at least two lives cut prematurely short—and retrospective regret—a sermon delivered by a man with a non-zero chance of being the actual antichrist—more power to you. Personally, I don’t know what to do with all this ickiness, other than refuse to ignore it.

Was this song a knockout blow? Yes and no. It’s an impeccable, fell strike, with nothing left to hit. —Lex Pryor

54. “Flex Freestyle,” Drakeo the Ruler

Year: 2016

Target: RJ

What’s the most vicious part of this song? The sheer disdain that Drakeo had for his sometime enemy, the South Central rapper RJ. One of the Ruler’s secret weapons was his ability to turn contempt into hilarity. On a diss aimed at one of the most prominent names of mid-2010s L.A. hip-hop, Drakeo made it seem as if his rival should be grateful that he was getting more than a half a bar. He waves his arms at him like a Bourbon monarch disgustedly sending back an undercooked roast turkey and ordering the chef to be beheaded.

Drakeo was a fan of the battle rapper Cocky, which meant that he had at least partially absorbed the lessons of the best artists in that medium—a genre aptly distilled by the famous adage: “If you want to tell people the truth, make them laugh, otherwise they’ll kill you.” After all, the song begins: “Sheesh, everything I state is facts / I’m not these other street n—-s, bitch I can really rap.”

Most of the track is devoted to confirming why Drakeo was the most influential West Coast street rapper of the past decade (and if you don’t believe me, just listen to Kendrick Lamar’s flow on “Not Like Us”). His slang, his cadences, and his ability to balance absurd comedy with lethal realities remain inimitable—no matter how frequently they’re borrowed. Here Drakeo mentions “shootin’ Ks on Naomi” (one of the streets where he grew up), then in a quick aside mocks the racist LAPD (“police like that’s Black people”).

Like most of the best writers, Drakeo was a master of concision. In his few actual attack bars, he distills his rival’s whole aesthetic into a few sentences that undermine his entire persona: “He the type of n—- put slashes in his eyebrows / Pigtail flattops? Please tell me what’s that about.”

If other artists on this list resorted to investigative reports to permanently wound their rivals, Drakeo did his hits like a spy slipping ricin into someone’s green tea. Quickly, efficiently, and leaving fatal damage to the central nervous system. In targeting the older rapper, he practically cackles:

Thirty-two, what if rap don’t work? He ain’t got no hustle

Watch worth 25, where was you at 25?

Nothing so vicious has ever seemed this effortless.

What’s this song’s legacy? For all the unimpeachable facts, Drakeo was clearly an artist using hyperbole and satire to create something indelible. Unlike the boasts in the song, Drakeo didn’t have RJ tied up in the trunk of his Jaguar. He didn’t even have a Jaguar. Nor did he ever wield a tommy gun. But none of this stopped the Los Angeles County District Attorney’s office from using the “Flex Freestyle” as evidence in its case to prove that Drakeo wanted to murder his rap rival.

No matter how much Drakeo or RJ publicly denied that their beef ever went deeper than vying for the throne of Mr. L.A., law enforcement refused to take them at their word—leading to one of the darkest chapters in the ignominious history of rap and the First Amendment. Only a few years later, you can still see this same prosecutorial overreach at Young Thug’s RICO trial, in which otherwise boilerplate rap braggadocio is being weaponized against him.

Who caught the worst stray? The city of Redondo Beach. Technically, the stray wasn’t a part of the “Flex Freestyle,” but at the height of the conflict, Drakeo did an interview on a local YouTube channel that was also later used against him at his murder trial. During the interview, Drakeo claimed that RJ was a backup dancer from Redondo Beach. None of this was remotely true, but it was an all-time great achievement of lies used for comic effect in rap beef. —Jeff Weiss

53. “Destroy and Rebuild,” Nas

Year: 2001

Target: Cormega, Mobb Deep

What’s the most vicious part of this song? “Destroy and Rebuild” is the closest thing to an actual noogie that we’ve encountered in rap. It’s not on this list merely because it’s efficiently brutal or slick as hell or littered with a combination of paternalistic barbs and Five Percenter lingua franca: The reason we let Nas get away with ending a song that accuses his inner borough enemies of “hating me cuz I’m beautiful” is because we’d just watched the man essentially put verbal knuckles to scalps.

What’s this song’s legacy? Besides the eternal image of an infant Nasir Jones bedecked in suede Ballys and silks? This is the song that confirmed QB had never been driven beneath the earth—and that no amount of infighting could ever truly degrade it so long as Nastradamus drew breath. (Even if he fell, he’d just crawl up out of the grave, wipe the dirt, clean his shirt, and hatch another classic.)

Was Nas punching up or down—and does that matter? Did Esco have to tell another grown man “I can’t hold your hand” or be “your father” (after he’d already called him “Buckwheat”)? Only He can truly say. —Pryor

52. “99 Problems (Lil Flip Ain’t One),” T.I.

Year: 2004

Target: Lil’ Flip

What’s the most vicious part of this song? T.I. held nothing back on either verse (“Lyrically, I’ll murk you, physically I’ll hurt you” is the gist of the song), but the two minutes of shit talk he unleashes afterward put this over the top. After mercilessly cutting Lil’ Flip down to size, he takes the time to gloat, calling him a fraud and ridiculing him for wearing that infamous leprechaun suit.

You can hear Tip laughing and almost picture the smug grin on his face as he asks: “Could I please get a glitter bow tie and a top hat, please?”

It’s ruthless and offers a glimpse of Tip’s sense of humor.

What’s this song’s legacy? This showed how effective Tip could be at channeling his aggression, unbridled rage, and abundance of charm into a lyrical onslaught. It’s also a reminder that, at one point, these two were in a similar stratum—as well as how quickly that can change.

Was this song a knockout blow? Not immediately. After the song appeared on Tip’s Down With the King mixtape, the two got into a fight in Flip’s Houston neighborhood in March 2005. But moving forward, Tip took increasingly bigger leaps toward becoming one of the defining rappers of his generation. Lil’ Flip, on the other hand, was never anywhere near as popular. —Kimble

51. “Lost Ones,” Lauryn Hill

Year: 1998

Target: Wyclef Jean

What’s the most vicious part of this song? “Now, now, how come your talk turn cold? / Gained the whole world for the price of your soul / Tryin’ to grab a hold of what you can’t control / Now you’re all floss—what a sight to behold”

The second verse begins with a master class in expressing unadulterated contempt without wasting a word. There’s a particular way that someone who knows you entirely too well can cut you down to size, reducing you to your worst tendencies because they see you for exactly who and what you are. With just a few bars, Hill wields her righteous indignation like a scalpel.

What’s this song’s legacy? In addition to setting the agenda for one of the most well-regarded albums of the past 30 years, “Lost Ones” pulled back the curtain on Fugees’s split. Although Hill never mentioned Wyclef by name, she didn’t have to. Through the years, he opened up about how the dissolution of their relationship led to the group’s demise, but he’d have to work around the darts she threw at his personal and artistic integrity.

Was Lauryn punching up or down—and does that matter? Hill was punching up. This was part of the process of liberating herself from a personal and professional relationship that turned toxic. On top of that, the decision to be specific without naming names ensured that the intended audience of one knew exactly whom it was for. —Kimble

50. “Fuck KD,” Lil B

Year: 2014

Target: Kevin Durant

What’s the most vicious part of this song? While the verses lack the focused, pure vitriol of many of these songs, Lil B makes up for it with a simple yet hilariously vicious hook. There’s something so fun and freeing about singing “Fuuuuuuuuuuuuck Kevin Duraaaaaaaaaaaaaaaaaaant,” whether you’re a fan of his or not. If you had KD do a lie detector test, I bet even he’d admit that he sings the hook when nobody’s listening. I just hope the man said “Thank you, Basedgod” when he joined the Warriors and was blessed by the removal of the curse.

What’s this song’s legacy? Bay Area legend and deity Lil B placed a five-year curse on Durant’s championship aspirations that eventually forced him to join the Warriors in the hopes of getting on the Basedgod’s good side.

This record came out after KD called Lil B’s music wack and became a certified Basedgod nonbeliever. And after the years of heartbreak that followed in OKC, I bet KD wished he could take his slander back. If you listened hard enough, the spirit of the Basedgod’s shrieks followed Durant everywhere: when the heavens assisted with a friendly bounce on Tim Duncan’s turnaround jumper in OT of Game 6 of the Spurs-Thunder Western Conference finals, in an injury-marred 2015, or when the Thunder totally collapsed and gave up a 3-1 lead against the Warriors in 2016.

Was Lil B punching up or down—and does that matter? If we’re talking physically, Lil B would have to punch way, way, way up to graze Durant’s chin. But if we’re talking spiritually, there’s nothing above the metaphysical being that is Basedgod, who sits above all and can only punch down. —Kermah

49. “Def Wish” Parts I-IV, MC Eiht and Compton’s Most Wanted

Year(s): 1991-1996

Target: DJ Quik

What’s the most vicious part of these songs? The simple fact that there are four of them, spread out over five years. If you think Kendrick hates Drake, imagine the hate it took to pump out these songs for a half decade.

What’s these songs’ legacy? It may have started with a simple misunderstanding. The basic story goes like this: Quik mentions Eiht’s group Compton’s Most Wanted on an early self-released mixtape, then Eiht makes a song called “Def Wish” that uses the word quick—which he claims was an unrelated reference. (The truth was even more offensive: Eiht says he had no idea who DJ Quik was at the time.) Quik gets signed to Profile Records and responds to the perceived slight on “Way 2 Fonky,” and from there the gloves come off. They’d respond back and forth for years—and Quik may have had the best entry in the feud with “Dollaz + Sense”—but Eiht had the funniest, particularly with “Def Wish III.” (“DJ Quik in a khaki bikini”!) Still, given both rappers’ rival gang affiliations, perhaps the most important legacy of this beef is that it ultimately remained on wax, despite moments when it looked like it wouldn’t.

What’s your favorite behind-the-scenes thing about these songs? The diss tracks stopped in 1996, but the feud simmered for years, until 1999, when they squashed it on Tavis Smiley’s late-night BET show. Eiht and Quik would eventually collaborate, though those songs have yet to surface. —Sayles

48. “Family Matters,” Drake

Year: 2024

Target: Kendrick Lamar, Rick Ross, Metro Boomin, the Weeknd, A$AP Rocky

What’s the most vicious part of this song? There are scathing—scathing!—disses in here that go beyond just Drake’s (extremely unconfirmed) comments claiming that Kendrick physically assaulted the mother of his children. There are the accusations that Kendrick is the one wrestling with his racial identity, Drake’s claim that he heard a rumor that one of Kendrick’s kids could be Dave Free’s, and varying degrees of hatred directed at the Weeknd and his manager. But the person who caught the worst of it was A$AP Rocky, who was dismissed—accurately—as Rihanna’s eye candy and someone who’s incapable of making a decent record in 2024.

What’s this song’s legacy? Will you remember the best game that the Toronto Raptors played this season? That’s what this feels like: the best moment of a losing campaign, destined to be forgotten because what good is there in celebrating a victory amid all these losses? “Family Matters” was Drake’s “nuclear” option, and it may have worked if Kendrick hadn’t had a heat-seeking missile ready to take it down. About an hour after Drake dropped this three-part song, Kendrick made “Meet the Grahams” public, totally blunting the impact of “Family Matters” and blocking any path Drake had to victory.

Who caught the worst stray? Let me answer that question the opposite way: Who came out of this looking cooler than Future, the guy that Drake repeatedly refused to diss because … well, he’s too damn cool? —Sayles

47. “10% Dis,” MC Lyte

Year: 1988

Target: Antoinette

What’s the most vicious part of this song? “You should’ve won a prize as a Rakim soundalike.” What makes “10% Dis” so searing is that MC Lyte’s appraisals of Antoinette are, at least in theory, incidental. The offense that sparked the song was the latter’s perceived biting of Audio Two’s “Top Billin,” and the dismantling, Lyte would later say, was “just business.”

What’s this song’s legacy? In alleging that Antoinette is a biter, a follower, and a fraud who doesn’t write her own raps, Lyte presents herself as the opposite—as unassailably authentic, a reputation that would (deservedly) follow her through her career.

Was MC Lyte punching up or down—and does that matter? It can’t matter too much, because Lyte wasn’t even sure whom she was punching. In Brian Coleman’s Check the Technique, which details the recording of 36 rap LPs, Lyte is quoted as saying that she knew next to nothing about Antoinette when she went into the studio to write the song. (“I think she was from Queens,” Lyte says.) That the insults seem so motivated is incontrovertible evidence of Lyte’s genius as a performer. —Thompson

46. “Stay Strapped,” Young Jeezy

Year: 2005

Target: Gucci Mane

What’s the most vicious part of this song? The sprawling, shit-talking outro, which goes on for nearly three minutes—and includes Jeezy offering a $10,000 bounty for anybody who could snatch Gucci’s famed chain.

What’s this song’s legacy? Jeezy’s most prominent salvo in the most famous rap beef in Atlanta history. As in many of the tracks on this list, the bad blood starts with a collaboration between the two artists in question. In 2004, Jeezy and Gucci linked to record the song “Icy.” It ultimately landed on Gucci’s Trap House album and became both men’s breakout hit, but Jeezy would later claim he was never paid royalties for it. Thus began the animosity, which lasted for 15 years.

“Stay Strapped” lives on in infamy because of that bounty. In May 2005, Gucci was visiting a female friend when four men broke in and began insulting him. One—a rapper signed to Jeezy’s label who went by the name Pookie Loc—was later found dead. Gucci was charged with murder, but he maintained that he was acting in self-defense. (The charges were dropped in 2006 because of a lack of evidence.) For his part, Jeezy has said that he didn’t send Pookie to attack Gucci, rapping in 2015’s “Forgive Me,” “Lord knows I ain’t send the homie on no dummy mission.”

Was this song a knockout blow? Given the context, it’s hard to assess this song in that light. But as you’ll see higher up on this list, Gucci had the best song to come out of this feud. Both rappers would go on to achieve fame that was unthinkable when they first recorded “Icy”—Jeezy was one of the most successful artists of his generation, Gucci perhaps the most influential—but beef lingered over all of it. It would be that way until the two men squared off in perhaps the most tense Verzuz showdown of the pandemic—which climaxed when Jeezy and Gucci performed “Icy” together for the first time. (Though Gucci may have reopened the old wounds by invoking the “ghost of Pookie” in a song just two years later.) —Sayles

45. “Exodus 23:1,” Pusha T

Year: 2012

Targets: Lil Wayne, Drake, YMCMB

What’s the most vicious part of this song?: Lines like “Now you out here all by yourself / Ask Steve Jobs, wealth don’t buy health” hit different when you chart the paranoia-soaked lines throughout Drake’s music over the years.

What’s this song’s legacy? Without saying any names, Pusha T dropped a record so heated that it had Lil Wayne tweeting, “Fuk pusha t and anybody that love em,” while Kid Cudi wanted to let Push know that he loved him. That record, “Exodus 23:1,” was Pusha T as GOOD Music’s darling puffing out his chest and firing back at years of perceived disses from Wayne and the Young Money/Cash Money crew, including some shots (and cautionary pleas) thrown at Drake. It also marks the true start of Drake’s first real loss in the rap game; in 2018 Pusha T dropped “The Story of Adidon,” exposing the fact that Drake had a son no one knew about (and would reportedly be presenting his child to the world with an Adidas campaign).

Was this song a knockout blow? Not by a long shot. Drake weathered the storm, continuing to be the biggest artist in the hip-hop industry, but Pusha T did show that Drake could be beaten—something he’d prove again six years later. —khal

44. “Blueprint 2,” Jay-Z

Year: 2002

Target: Nas

What’s the most vicious part of this song? “’Cause a n—a wear a kufi, it don’t mean that he bright / ’Cause you don’t understand him, it don’t mean that he nice / It just means you don’t understand all the bullshit that he writes / Is it ‘Oochie Wally Wally,’ or is it ‘One Mic’? / Is it ‘Black Girl Lost,’ or shorty owe you for ice?”

Nas certainly was not the first or most famous rapper to egregiously contradict himself by presenting the duality of the principled scholar vs. the obnoxious fuckboy (see: Shakur, Tupac). But the way that Jay called him out on it cut deep. In their heavyweight feud, Nas was the Kendrick Lamar to Jay-Z’s Drake—the rap snob’s favorite battling the mainstream maven. And when the purists’ darling gets read for filth, it hits harder. Jay-Z’s bars also reminded everyone of some of Nas’s notable swings and misses at crossover club tracks, something Jay was always better at.

What’s this song’s legacy? It wasn’t the best song in the beef between Jay-Z and Nas. (That would be “Ether.”) It wasn’t even Jay-Z’s best song in the beef between Jay-Z and Nas. (That would be “Takeover.”) Nor was it the most controversial song in their back-and-forth. (That would be “Super Ugly.”) Because it came after the feud’s 2001 peak, “Blueprint 2” could even get buried in some historians’ inaccurate retellings (the ones in which Nas ended things with “Ether”). And yet Hova is sharp as ever on this track: “You’re an actor, you’re not who you’re depicted to be / You street dreamin’, all y’all n—-s livin’ through me / I gave you life when n—-s was forgettin’ you emcee.” In another beef, in another time, this track could’ve been a game winner.

Was Jay-Z punching up or down—and does that matter? Jay-Z vs. Nas was as evenly matched as a rap beef can get, which is why it’s so famous in the genre. Jay and Nas were back then, and are to this day, titans of hip-hop. They both came up around the same time, became legends during the 1990s glory days, and are still elite in the 2020s. And it didn’t get any bigger than New York as the grand stage for their rivalry. The timing was also just right: This wasn’t young Osaka smoking old Serena; this wasn’t old Mayweather schooling young Canelo; this was prime-for-prime Kobe vs. T-Mac, masters meeting at the pinnacle of their powers. —Burton

43. “Fuck Beanie Freestyle,” Jadakiss

Year: 2001

Target: Beanie Sigel

What’s the most vicious part of this song? We debated putting “Breakin’ the Rules Freestyle” here instead—Styles P’s “You could suck my dick with the shit on it” is as visceral of a line as you’ll ever hear on a diss track. But in the end, you gotta go with the classics. And by “classics,” I mean lines like these:

• “And I don’t know where they found you son / But since ya pops ain’t around I’mma punish you and ground you son.”
• “When I see you, I’mma put ya cornrows on the yellow lines.”
• “Fuck Scarface, my bullets hit women and kids.”

Well then!

What’s this song’s legacy? Beanie and Jada is one of the great rap beefs of the mixtape era—two of the best bar-for-bar rappers of the early aughts, at the height of their crafts, going at each other. But what we’ll remember most is the pure, unadulterated vitriol. If you think today’s rap beefs are tough to stomach, I’ve got a few Streetsweepers to play you.

What’s your favorite behind-the-scenes detail about this song? A decade later, after somehow making peace with Beanie and looking back at the beef on MTV, Jada said, “I think it was therapeutic for hip-hop.” I agree, so long as therapy is a safe space to say, “So when I shoot him in his face, I don’t wanna hear that I’m wrong neither.” —Sayles

42. “Have a Nice Day,” Roxanne Shanté

Year: 1987

Target: Boogie Down Productions

What’s the most vicious part of this song? It has to be when she tells KRS-One that his name sounds like “a wack radio station.”

What’s this song’s legacy? Tempting as it is—especially after a week spent parsing the allegations in “Family Matters” and “Meet the Grahams”—to look back on “The Bridge Is Over” as a relic of a more wholesome time, when rap beef was all about spirited competition between artists, you’re forced to remember that one line: “Roxanne Shanté is only good for steady fuckin’.” The self-proclaimed queen of the Juice Crew made it clear, though, that she wasn’t going to let that slide.

Was Roxanne punching up or down—and does it matter? The challenger-champion dynamics in the Bridge Wars splinter in a few different directions: Marley Marl et al. were the established artists and Boogie Down Productions the upstarts, though the Bronx natives were insistent that hip-hop was their birthright. But from any angle, a young woman in hip-hop was starting out at a disadvantage. —Thompson

41. “Real,” Freddie Gibbs and Madlib

Year: 2014

Target: Jeezy

What’s the most vicious part of this song? Near the end of the second verse, Freddie Gibbs goes for a knockout: “Seen Gucci by himself when he was 30 deep in Magic, and you didn’t bust a grape / Was shook from the gate, it make it seem to me the gangsta shit you kick be fake.” The idea of Gucci by himself while Jeezy refuses to do anything—despite the level of disrespect that Gucci had been sending toward Jeezy—is a startling image. Gibbs, a man who hails from Gary, Indiana, could not abide by that.

What’s this song’s legacy? It’s an example of the politics of the industry. Freddie Gibbs was incensed by Jeezy’s mishandling of the CTE World label that he had signed to. He’d later say that because of their business disagreement, he lost his “composure.” But as a song, “Real” is simply an excellent deep cut on an album that is strictly for the rapheads. Gibbs is one of the very best gangster rappers of his generation, and this track is a part of that legacy.

Was Freddie Gibbs punching up or down—and does it matter? Up. Beef is something that makes the most sense if the person is on your level of celebrity and stardom and y’all have unsettled issues with each other, or if you are a scrappy upstart trying to make a name for himself (see: Cent, 50). Gibbs was trying to knock one of the biggest rappers of his generation off his high horse, and he does, executing an excellent diss track with fury and precision. He nicknames himself “Snowman Killa,” and it’s an understatement. —Buford

40. “The Ripper Strikes Back,” LL Cool J

Year: 1998

Target: Canibus, Wyclef

What’s the most vicious part of this song? “Ask Canibus, he ain’t understanding this / ’Cause 99 percent of his fans don’t exist / I’m going underground and blowing your rep down / Next time, save that shit for the Lyricist Lounge / Or a house party, where you can battle some clown.”

The up-and-coming Canibus took a shot at the king, and while the kid didn’t miss, the king fired back with deadly force. “Second Round K.O.” is still regarded as an all-time diss track, but LL Cool J arguably won the beef because “The Ripper Strikes Back” put Canibus firmly in his place. After the youngster spit “99 percent of your fans wear high heels,” LL’s callback reminded Canibus that at least he had fans, and he wasn’t afraid to take his mainstream-celebrity ass underground to deal with a hotshot rookie.

What’s this song’s legacy? Add Canibus to a hit list that includes Kool Moe Dee and Ice-T, which puts LL on the short list of rap beef’s most prolific competitors. In fact, the target that was once on LL’s back may have reappeared on Drake: the crossover star, the one that the ladies love, the one whose arrogant persona no doubt annoys fellow MCs. It’s not hard to tell why they’re constantly being tested.

Who caught the worst stray? Mike Tyson. And, yeah, we’ve all seen how LL Cool J is built—but it was a brave move to talk shit about Mike Tyson in the 1990s. The former heavyweight champ was still in his 30s back then, still fighting professionally and knocking guys out while frightening the general public. However, Iron Mike’s guest appearance on “Second Round K.O.” put him in LL’s crosshairs: “Heard that convicted rapist on the record, too / Fresh out of jail, ass cheeks still black and blue / Tell me about the things Ear-Biter taught you / How to bust a nut or two?” —Burton

39. “Curtis,” Cam’ron

Year: 2007

Target: 50 Cent

What’s the most vicious part of this song? The video. Razor toothed as Cam’ron’s 2007 diss of 50 Cent is, no line—not even the invocation of Kenneth McGriff—cuts as deep as the scenes of New Yorkers, up to and including a uniformed police officer who taunts 50 with his government name.

What’s this song’s legacy? “Curtis” alone didn’t alter the trajectory of 50’s career, but it certainly dulled its shine. By 2007, 50 was beginning a sharp creative and commercial decline, and the qualities that had buoyed him in the public eye (an acid-dipped sense of humor, a Sun-Tzu-for-YouTube mean streak) were even more evident in Cam.

Was this song a knockout blow? At the beginning and end of his time atop rap’s food chain, 50 was involved in beefs that indicated where the entire ecosystem was headed. First he single-handedly ended Ja Rule’s pop chart dominance; later, when he was feuding with Rick Ross, he wrongly assumed that Ross’s past as a corrections officer would be a trump card. It was a sign that we were moving into an era when digital-native narratives were becoming untethered from old notions of reality. “Curtis” was not so much a cause of 50’s downfall as a symptom of it—even two years prior, it would have been unthinkable that another rapper, even one as battle-tested as Cam, could have released such a gleefully derisive song. —Thompson

38. “Live by Yo Rep (Bone Dis),” Three 6 Mafia

Year: 1995

Target: Bone Thugs-N-Harmony

What’s the most vicious part of this song? “Well, I shall take a thousand razor blades and press them in their flesh / Take my pitchfork out the fire, soak it in their chest.” Early Triple 6 did not really mess around.

What’s this song’s legacy? Biting was one of the cardinal sins of ’90s hip-hop. Originality was everything during this era, so when the Memphis collective Three 6 Mafia caught wind that Cleveland’s Bone Thugs-N-Harmony was making double-time raps and demonic content, they immediately threw a flag on the play. They accused Bone of appropriating the style they’d heard in Three 6 Mafia’s underground tapes—which had somehow traveled from Memphis to Cleveland.

Very few people outside Tennessee were familiar with Three 6 Mafia at the time, but they put themselves on the rap map by releasing an entire EP dedicated to dissing the Bone Thugs crew—arguably the most popular rap group at the time.

“Live by Yo Rep” made Three 6 Mafia a nationally known act. Nothing moves the needle like a good diss record, and even though Three 6 didn’t call Bones out by name (other than “Breakin’ motherfuckin bones like it ain’t shit”), stores across the country began stocking their product. The EP even landed them a national distribution deal with Relativity Records—which also happened to be the home of Bone Thugs-N-Harmony’s label, Ruthless Records.

Was this song a knockout blow? Absolutely not. Bone was too big to fail at that moment. But it did open the door for more attacks on the group, who had their hands full against other Midwest choppers like Twista, Do or Die, and Crucial Conflict.

What’s your favorite behind-the-scenes thing about this song? After ending up on the same Relativity Records conference call a few years later, the two factions decided the beef was much ado about nothing and put their differences to the side, eventually collaborating on Project Pat’s debut album, Ghetty Green (see “Up There,” featuring Krayzie Bone). However, it appeared the wounds weren’t 100 percent healed, as the two groups had a minor altercation at their Verzus battle in 2021. —Barber

37. “Quitter,” Eminem featuring D12

Year: 2000

Target: Everlast

What’s the most vicious part of this song? Like all the best diss tracks, it’s nearly seven minutes long, and roughly five of them are spent mocking Everlast for having a heart attack. But the rest—in which Em mostly accuses the former House of Pain frontman of making a calculated transition from rap to rock, only to be surpassed by Limp Bizkit—is more than enough to send its target back to the ICU.

What’s this song’s legacy? This beef started when Everlast tried to land a not-really-that-clever jab at Em on a Dilated Peoples track—“Cock my hammer, spit a comet like Halley / I’ll buck a .380 on ones that act Shady”—but it effectively ended here, with Marshall Mathers and D12 riding on Whitey Ford over the “Hit ’Em Up” beat. (Though it’s worth shouting out Evidence from Dilated Peoples’ pretty great response, “Searching 4 Bobby Fischer,” which gets lost in these discussions.) Still, it’s hard not to view this as yet another example of Eminem wasting a lot of oxygen on an opponent who wasn’t really worth it. To that point …

Was Eminem punching up or down—and does that matter? You can argue that Eminem has never really punched up in a rap battle. His list of roadkill is on the LeBron-in-the-Eastern-Conference level: Everlast, Limp Bizkit, Canibus, ICP, Benzino, Nick Cannon, Machine Gun Kelly, and on and on. He’s unquestionably one of the most talented rappers ever, and he’s one of the last people you’d want dissing you, but at a certain point, wouldn’t it have been nice to see him fight someone in his weight class? —Sayles

36. “Kiss the Game Goodbye (Freestyle),” Beanie Sigel

Year: 2001

Target: Jadakiss

What’s the most vicious part of this song? “What’s funny, Jason? / Really think you grimy, too / And everybody liked you better in that shiny suit.”

What’s this song’s legacy? You’ll notice that no one else in hip-hop was really trying to antagonize Beanie Sigel after this beef, at least not until Jay and Kanye threw him under the bus on Watch the Throne.

Was this song a knockout blow? Beans and Kiss both performed rather admirably, their respective disses are great in their own ways, and the end result is a gentleman’s draw. —Justin Charity

35. “Euphoria,” Kendrick Lamar

Year: 2024

Target: Drake

What’s the most vicious part of this song? “You don’t know nothing ’bout that.”

What’s this song’s legacy? Drake and his core fan base seemed to believe that they’d run out the statute of limitations on complaining about the authenticity of a biracial child actor from the suburbs of Toronto turned hardbody R&B thug. But Kendrick seems determined to reopen these outstanding criticisms in a big way that Drake can’t simply outrun.

Was this song a knockout blow? No. The outcome of this feud now largely hinges on Drake’s potential participation in—and the outcome of—the #bbldrizzybeatgiveaway. —Charity

34. “Shark N—-s (Biters),” Raekwon

Year: 1995

Target: The Notorious B.I.G., biters in general

What’s the most vicious part of this interlude? “Get your own shit, man—and be original.” The only entry on this list that isn’t a song is perhaps rap’s most famous skit, a structureless 98-second rant from Ghostface and Raekwon about the legions of imitators who, at some point in 1994, came crawling out of every crevice in every borough. “They hear you say one word, then here they come with the word.” Pitiful.

What’s this track’s legacy? It helps cement Ghost and Rae as what they were: innovators of the highest order, prodded and picked apart and imitated ad nauseam but never quite replicated.

Who caught the worst stray? Biggie. While most of the barbs are general enough to apply to any number of rappers—and this is in part the point; everyone wanted to be Wu—the one unambiguous shot is at the Ready to Die album cover, which Ghost and Rae consider a rip-off of Nas’s Illmatic. While the aesthetic styles are totally different (a baby against an all-white void versus a young person’s face melting into a cityscape), the image of the artist as a young man was enough to hit the trip wire. —Thompson

33. “Calling Out Names,” Kurupt

Year: 1999

Target: DMX, Foxy Brown, Irv Gotti, Ja Rule, 50 Cent, Nas, AZ, the movie Belly

What’s the most vicious part of this song? “Mothafuck D, Mothafuck M, Only X I know is Xzibit or RBX / Extraordinary, tryna snatch my bitch / You can have the bitch, two bitches gettin’ rich”—just an extremely disrespectful collection of words.

What’s this song’s legacy? After catching wind of an alleged affair between DMX and Kurupt’s ex-fiancée, Foxy Brown, Kurupt said fuck a subliminal and started calling out actual names (a lost art these days).

Anyone within earshot of DMX and Foxy (who were also Def Jam labelmates) was put in the hot seat, with the likes of Murder Inc., Ruff Ryders (But he gave the Lox and Eve a pass, so who was he dissing? Drag-On?), and the Firm feeling the brunt of it.

But did it hurt Kurupt’s solo career? Maybe. In June 1998, DMX, Silkk the Shocker, and Kurupt graced The Source magazine’s “Rap’s New Generation” cover, which touted them as the future of the genre. Kurupt was a solid pick, as just a few years prior he had topped the charts as part of Tha Dogg Pound. But he had struggled to find his footing without the Death Row machine, and his solo debut, Kuruption, was met with less than favorable reviews and poor sales. But while Kurupt fizzled, DMX ascended to the top of the business, becoming the biggest success story of 1998—and allegedly saving Def Jam.

In 1999, Kurupt dusted himself off and returned with his sophomore solo shot, Tha Streetz Iz a Mutha, which was a superior album across the board—a project many consider to be a classic. But rumors swirled that the industry was blackballing Kurupt for attacking Def Jam’s darlings (DMX, Ja Rule, and Foxy Brown), which slowed down his sales, airplay, and overall opportunities.

Who caught the worst stray? “Callin Out Names” could be best remembered as the first time a rapper dissed an entire movie cast: “Fuck Belly.”

What’s your favorite behind-the-scenes thing about this song? While the beef was quickly swept under the rug before the ’90s came to a close, it took DMX and Kurupt nearly 20 years to meet face-to-face, in a chance encounter at LAX. The two became fast friends and sat at an airport bar for hours while making up for lost time. And yes, they both missed their respective flights. —Barber

32. “Play Wit Yo Bitch,” Young Dolph

Year: 2017

Target: Yo Gotti

What’s the most vicious part of this song? One gets the sense that Young Dolph feels embarrassed to even address his hometown rival by name. To get around this humiliation, he creates a clever new nickname for Yo Gotti and his Collective Music Group label, christening the label boss “Ho Gotti” and his crew the “Cocaine Muzik F——.” The song became the first public shot in a local Memphis beef that had been brewing for the better part of a decade. Young Dolph insists that Yo Gotti should pick on someone his own size, chiding the “Down in the DM” rapper for beefing with V Slash, a Three 6 Mafia affiliate whom Yo Gotti had dissed in 2010.

What’s this song’s legacy? There’s a bittersweet quality to a song like “Play Wit Yo Bitch” since Young Dolph was killed while buying cookies for his mother in November 2021. The song itself was and is a major blow against CMG, not only because Dolph and Zaytoven make better music than Yo Gotti’s entire roster does, but because it revealed, once and for all, that Memphs belonged to Young Dolph. That fact became all the more clear in the wake of his death, when lawmakers called for a curfew to prevent rioting and civil unrest.

Was this song a knockout blow? The Zaytoven production and the way “Play Wit Yo Bitch” almost just reads as a normal strip club banger makes this a complete knockout blow. There was—and still is—nobody in the CMG camp capable of going toe to toe with Young Dolph. In the wake of this diss, Young Dolph and his Paper Route Empire became the biggest rap export coming out of Memphis. He had the heart of the city and was beginning to grow his label and continue various philanthropic endeavors before his life was cut short. —Morrison

31. “L.A., L.A.,” Capone-n-Noreaga featuring Mobb Deep and Tragedy Khadafi

Year: 1996

Target: Tha Dogg Pound

What’s the most vicious part of this song? This was a reply to Tha Dogg Pound and Snoop Dogg’s “New York, New York,” and Tragedy Khadafi has the hardest verse, per usual, but the song doesn’t feature any explicit disses.

“If you really listen to ‘L.A., L.A.,’ the concept is dissing them but the actual song has no disses at all,” Noreaga told Complex in 2010. “The thing was, as we was listening to ‘New York, New York,’ we couldn’t find no disses from them either. So we just figured we’ll respond the same way they attacked us.”

That meant via music video. So where Snoop, Daz, and Kurupt stomped all over New York City, CNN and Tragedy Khadafi kidnapped fictional versions of Tha Dogg Pound and tossed them off a project building rooftop and the 59th Street Bridge.

What’s this song’s legacy? “L.A., L.A.” is remembered as a tangential moment in the East Coast–West Coast conflict, but it was also instrumental in CNN’s rise. “That record made us to the point where people were like, ‘These guys right here is going to make a mark in the hip-hop game,’” Capone told Complex.

By the time their debut album, The War Report, was released the following year, the duo had made a name for themselves by jumping into one of hip-hop’s most controversial moments.

Was CNN punching up or down—and does that matter? Mobb Deep was established, but CNN was definitely punching up. —Kimble

30. “Fuck Compton,” Tim Dog

Year: 1991

Target: N.W.A, Michel’le, the greater Compton area

What’s the most vicious part of this song? Tim Dog’s Penicillin on Wax is basically a diss album and “Fuck Compton” is the mission statement. Not content to just go after N.W.A, Dog targeted the entire city they repped, claiming that its fearsome reputation had nothing on the South Bronx. Also, why were they wearing all that Raiders gear when the Giants won the Super Bowl? What the Ultramagnetic MCs affiliate lacked in lyrical dexterity, he made up for with bluntness, like when he says that when it comes to Eazy-E, he’ll “chew him with tobacco and spit him in shit.” But as Tim Dog puts it a few bars later, “I’m simplistic, imperialistic, idealistic / And I’m kicking the ballistics.”

What’s this song’s legacy? N.W.A was already on their way to imploding when “Fuck Compton” was released, so the group never collectively responded to this unprovoked attack. But Snoop, back in his Doggy Dogg days, did dedicate the entire second verse of “Fuck Wit Dre Day (and Everybody’s Celebratin’)” to going after “Tim M-U-T [sic]” on the behalf of his mentor.

Who caught the worst stray? Michel’le—R&B singer, Ruthless Records signee, and Dr. Dre’s then-girlfriend—is the target of some junior-high-level taunts and impressions on “Fuck Compton.” Dog was right to call out Dre for physically assaulting rapper and TV host Dee Barnes on the song, and on the skit “Michel’le Conversation” from Penicillin on Wax, he said that Dre beat her too. Years later, Michel’le would corroborate these claims herself. Still, Tim Dog’s sexual taunts directed at her make him far from the good guy in this situation, and before his death in 2013, multiple women say he conned them out of their money. —Ducker

29. “Like That,” Future and Metro Boomin featuring Kendrick Lamar

Year: 2024

Target: Drake

What’s the most vicious part of this song? The foreshadowing of what was to come. When “Like That” dropped, Kendrick’s feature was the culmination of a decade-plus of fans waiting for him to go toe-to-toe with Drake—in what people assumed would be a fun battle. But Dot showed clues of his angst, calling out his disdain for Drake and J. Cole’s “First Person Shooter,” the 2023 song promoting unity among the genre’s three biggest rappers. If you’ve followed everything that’s been said in this feud since, you know that it’s only gotten heavier from there. This whole beef has turned into rap consumers watching with their jaws on the floor, nervously waiting for what’s next.

What’s this song’s legacy? Kendrick’s verse began the most consequential beef of the modern era—and the beginning of hip-hop’s rejection of its biggest star. Throughout the 2010s, Drake has positioned himself as the face of hip-hop’s growing infiltration of the mainstream. Under Aubrey’s watch, hip-hop has transformed from a genre that has periodically infiltrated pop culture to one that has made its every news cycle part of the public consciousness, for better or for worse. Lamar is the manifestation of hip-hop’s past growing tired of him. (That includes those who helped build Drizzy’s career in the first place—oh hey, Ross.) Since “Like That” was released, Drake’s peers, and frequent collaborators, are repeating a familiar refrain: He’s corny, an outsider, and doesn’t respect the culture he’s financially benefiting from. “Like That” gave everyone free rein to say what they were thinking.

Was Kendrick punching up or down—and does that matter? Kendrick is punching up, but it doesn’t matter. This has nothing to do with sales, notoriety, or one’s place in the rap game. It’s about a man’s hate for another man, and how far both are willing to take it. Thus far, Kenny has taken it the furthest. —Logan Murdock

28. “Kick in the Door,” the Notorious B.I.G.

Year: 1997

Targets: Nas, Raekwon, Ghostface Killah, Jeru the Damaja

What’s the most vicious part of this song? The last line. While “Kick in the Door” has venom for a number of unnamed targets—including Raekwon, whose “Ice Water” lyrics Big inverts in response to the suggestion that the Ready to Die cover was modeled on Illmatic—it opens and closes on Nas. And after three verses of menace and staggering technique, Big reduces his rival’s lot in life to five withering words: “And you still recoupin’, stupid.”

What’s this song’s legacy? It shows the greatest rapper to ever live at the absolute apex of his powers. Life After Death is the first (and, depending on how you feel about The Eminem Show and My Beautiful Dark Twisted Fantasy, perhaps only) masterpiece that is about being a rap star, and “Kick in the Door” hears him boast, convincingly, about being a sharper MC, a bigger box-office draw, and simply more likable than many of the most talented rappers alive. The track is so undeniable, in fact, that five years later, when Nas is debriefing listeners on his beef with Jay-Z on “Last Real N—- Alive,” he boasts about having been in Big’s crosshairs here.

Who caught the worst stray?: The producer, weirdly. “Son, I’m surprised you run with them,” Big quips to DJ Premier about Jeru the Damaja, whose first two albums Preemo had produced in their entirety, and who had made a remark about “hip-hop with a Versace suit on” on 1996’s “One Day.” —Thompson

27. “To Da Break of Dawn,” LL Cool J

Year: 1991

Target: Hammer, Ice-T, Kool Moe Dee

What’s the most vicious part of this song? In a song going after his longtime rival Kool Moe Dee and the chart-topper-of-the-moment in Hammer, LL reserves his most disrespectful bars for the Original Gangster. “Before you rapped, you was a downtown car thief / Workin’ in a parking lot / A brother with a perm deserves to get burned” may have been enough to make Ice-T quit rap for a while and start Body Count.

What’s this song’s legacy? It’s weird to think that at just 22, LL Cool J needed to make a little bit of a comeback, but that’s how Mama Said Knock You Out was positioned. The title track was obviously the massive hit that led that record, but the entire LP is an exercise in reasserting dominance. Nowhere is that more evident than on “To Da Break of Dawn”—maybe LL’s best diss song in a career loaded with them.

Who caught the worst stray? “I took the cover right home to the bathroom / In the immortal words of LL, ‘Hard as hell’ / Your broad wears it well” is insinuation that Ice-T’s records only sold because of their famous cover girl —and just an awful visual. I hope Darlene Ortiz is doing OK, wherever she is. —Sayles

26. “Against All Odds,” 2Pac (Makaveli)

Year: 1996

Target: The Notorious B.I.G., Mobb Deep, De La Soul, Diddy, Nas, Jay-Z, Jimmy Henchmen, Haitian Jack

What’s the most vicious part of this song? How freely Tupac names people who are allegedly out to see his demise. In Shakur’s eyes, Dr. Dre is a punk who can’t go back to his hood, Nas stole his style from Rakim, Puffy is getting robbed, and Haitian Jack set him up in Pac’s 1994 sexual assault case. It’s the ultimate war record from hip-hop’s biggest self-identified soldier fighting in rap’s most violent battle. It rivals, if not surpasses, Shakur’s magnum opus of lyrical combat “Hit ’Em Up,” if not in influence, then in vitriol. It’s a spooky, dark, and revealing record you can spin over and over and over again and still not fully realize how much contempt Shakur has in his heart for those who wronged him.

What’s this song’s legacy? It’s the last track on the first LP released following Shakur’s killing, giving an eerie look into Shakur’s mind in the final months of his life. In 1996, he was appealing the 1994 case in which he was found guilty of two counts of first-degree sexual abuse. He was in the middle of a famous feud with Bad Boy Records CEO Sean “Diddy” Combs and the Notorious B.I.G., the label’s biggest artist. And he was doing this while fighting the paranoia that comes with getting shot five times, which also happened in 1994, in an incident Shakur blamed on Combs and Biggie, his former friend. In “Against All Odds,” you can hear all of these elements exploding out on wax. Nearly 30 years after its release, I’m still getting chills listening to Pac recite the “truest shit [he’s] ever spoke.”

What’s your favorite behind-the-scenes thing about this song? This record was inspired by the bass line of Cameo’s 1988 single, “Skin I’m In,” a song that promotes world peace. —Murdock

25. “How Ya Like Me Now,” Kool Moe Dee

Year: 1987

Target: LL Cool J

What’s the most vicious part of this song? “I’m bigger and better, forget about deffer.” So many diss tracks are built on subliminal insults and cryptic references that sometimes it’s just nice to hear a direct shot taken at a plainly visible target that doesn’t require a trip down the rap Reddit rabbit hole to decipher. “How Ya Like Me Now” mirrors a lot of diss tracks in that the subject’s name is never brought up, but the “forget about deffer” line at least clears up any confusion over who Kool Moe Dee is talking to: A few months before this track dropped, LL Cool J released an album called Bigger and Deffer.

What’s this song’s legacy? It’s not so much the song as it is the album cover. “How Ya Like Me Now” (the song) is the opening track on How Ya Like Me Now (the album), and the cover art for that album features KMD flexing in front of a Jeep with its front wheel crushing a red Kangol hat—the same kind of red Kangol that LL Cool J is wearing on the cover of Bigger and Deffer.

It is a great moment in rap beef as a visual medium; you don’t have to hear one word of “How Ya Like Me Now” to know exactly how Kool Moe Dee feels about LL, who sparked the rivalry with seemingly harmless braggadocio bars calling himself “the new grand master” and claiming “I’m only 18 making more than your pops” on “The Do Wop.” (Bow Wow of all people would, years later, borrow the latter lyric; but he did not incur the wrath of any hip-hop elder statesmen with it.) While today’s pettiest and most celebrated musical agitators like Kendrick Lamar and, um, Taylor Swift, will have X detectives scouring every square inch of an image looking for a crumb of beef, that clear-as-day crushed Kangol from ’87 still holds a spot in the hearts of many fans of music-industry feuds.

Was this song a knockout blow? Far from a knockout, this was the knockdown that lit a fire under the now Hall of Fame rap-beef grill master that is LL Cool J. Think of Kool Moe Dee as the “Bad Boy” Detroit Pistons, and LL as a young Michael Jordan. LL came into the game all flashy and full of himself before Moe Dee leveled him with some elbows and judo throws, forcing LL to show what he was really made of. KMD thus played foil in the launching pad of LL’s rise to legendary status.

“How Ya Like Me Now” prompted LL to respond with “Jack the Ripper” (“How ya like me now, punk? You living foul / Here’s what my game is / Kill is what my aim is / A washed-up rapper needs a wash-up”). Kool Moe Dee came back with “Let’s Go” (“You need to sneak back to the drawing board, Jack / The Ripper, down with my zipper / You get paid to be a Moe Dee tipster”), and finally LL had the last dance with “To Da Break of Dawn” (“Brother, you’re dead wrong / And got the nerve to have them Star Trek shades on”) and “Mama Said Knock You Out” (“When I pull out my jammy get ready ’cause it might go blaow / How ya like me now?”). —Burton

24. “Back Down,” 50 Cent

Year: 2003

Target: Ja Rule

What’s the most vicious part of this song? The pronunciation of Ja Rule’s government name, Jeffrey Atkins, hasn’t sounded the same since the release of “Back Down,” where comedian and actor Alex Thomas does a startlingly convincing impression of what’s supposed to be Ja Rule’s stylist in outro. “Oh no, he didn’t say anything about Ja, OK? Ja is my boo, OK? Jeffrey Atkiiiiins ain’t never hurt nobody,” Thomas says imitating an effeminate male stylist. Thomas later revealed he didn’t even know who 50 Cent was at the time he did the recording, having instead been paid $10,000 by good friend Dr. Dre for the day’s work.

What’s this song’s legacy? “Back Down” is the centerpiece to one of the only true rap classics since the 2000s began. It marked the beginning of the end for Ja Rule and the Irv Gotti–led Murder Inc. Even aside from the dissing, some of 50 Cent’s best writing is in this song, which it’s why it’s still being listened to long after it’s been removed from the context of a fleeting rap feud.

50 Cent has always been known as a shit starter, and “Back Down”—with its hyperfixation on Ja Rule, coupled with the energy of a man who just survived being shot nine times—easily enters the pantheon of great diss records for the sheer damage it caused to the careers of Ja and the rest of Murder Inc. “You sing for hoes and sound like the Cookie Monster,” was so devastating that it killed the idea of the rapper/singer archetype for years, until Drake came around.

What’s your favorite behind-the-scenes thing about this song? Sha Money XL said in a recent interview that the original version of “Back Down” features lines going against Cam’ron, Nas, Jay-Z, R. Kelly, and convicted drug trafficker Kenneth “Supreme” McGriff. Apparently it was Dr. Dre who convinced 50 Cent to narrow his focus to just the Murder Inc. camp. Dr. Dre would diss Ja Rule and Irv Gotti in a verse on Obie Trice’s debut album not long after this. —Morrison

23. “You Gotta Love It,” Cam’ron featuring Max B

Year: 2006

Target: Jay-Z

What’s the most vicious part of this song? The most cocksurely disrespectful intro since “Hit ’Em Up.” “First off, you a bitch n—-,” starts the verbal assault. Then, after making Jay-Z out to be an executive who steals artists and clothing lines from his former rivals, Cam’ron stops the beat and lays waste to the then–Def Jam CEO: “You 37 years old / You was born in 1968 and I open up the Daily News / How’s the king of New York rockin’ sandals with jeans? / Open toe sandals with chancletas with jeans on / How’s the king of New York rockin’ sandals with jeans and he 42 years old?” Jay-Z became an instant punch line for all the Harlem dudes with Dipset shirts, jackets, and whose loyalty was always to Dame Dash.

What’s this song’s legacy? Jay-Z is an all-time great rapper—maybe the greatest of all time in terms of craft. But he’s also shockingly easy to make fun of, and this song is another in a long line of jokes about Hov’s awkwardness. Jay can somewhat forget about the streets that raised him, or at the very least appear oafishly wealthy on a beach. His goal was probably always to become the consciousness of the Black elite. But guys like Cam’ron don’t think about that at all. They just exist in the world. In 2006, Jay had traded his jerseys and Timbs for open toe sandals with jeans. Cam’ron and Max, in a show-stopping chorus, took this as a sign that he was no longer the king of New York.

Was this song a knockout blow? No, because Jay-Z is too certified, talented, and rich for it to be. Hov made it out of the jungle, with worse memories and traumas than any line that Cam’ron spat here. At some point, you become too famous for anything to knock the mantle that you’re standing on. Despite the fact he was pushing 40 and was possibly no longer the one, he was still Sir Carter of Brooklyn. —Buford

22. “300 Bars N Runnin’,” the Game

Year: 2005

Target: 50 Cent, G-Unit

What’s the most vicious part of this song? The beat changes, and Game switching flows to match, like he’s playing changes, hit harder and nastier than any of the lyrics in particular, honestly.

What’s this song’s legacy? 50 Cent made “How to Rob” and then trolled Ja Rule to death and thus earned his reputation as a master of rap beef. But he actually has a pretty weak track record of draws and losses—against Game, Jay-Z, Cam’ron, Nas, Rick Ross, et al.—and I’d say Game was the first rapper to put up a real fight against 50 and expose his mortality.

Who caught the worst stray? “I told Funk Flex, when I catch the n—- Whoo Kid / We gon see if he know how to DJ with bruised ribs.” —Charity

21. “South Bronx,” Boogie Down Productions

Year: 1986

Target: MC Shan

What’s the most vicious part of this song? KRS imploring Shan to stop worrying about LL Cool J and “take your homeboys off the crack” is a line that’s stuck with Shan for the rest of his career.

What’s this song’s legacy? “South Bronx” is the record that helped put KRS-One and Boogie Down Productions on the map. When it came down to deciding on the birthplace of hip-hop, the Juice Crew’s MC Shan planted the flag in Queensbridge with “The Bridge.” KRS-One of the Boogie Down Productions crew disagreed, penning “South Bronx,” not only detailing what he saw as the true origins of hip-hop culture, but also making a point to speak on how he “didn’t hear a PEEP” from anyone in Queens at the time.

Was BDP punching up or down—and does that matter? KRS was very much punching up, to his advantage. It was a wise play for the emerging BDP crew, the spark that led to the beginning of KRS-One and BDP as a whole making their mark on the culture, while this marked the beginning of the end of MC Shan’s time in hip-hop’s limelight. —khal

20. “The Bitch in Yoo,” Common

Year: 1996

Target: Ice Cube, WC, Mack 10

What’s the most vicious part of this song? Years before Jay asked Nas if “it’s ‘Oochie Wally’ or ‘One Mic,’” Common hit Cube for his hypocrisy with devastating simplicity when he called him out for “slangin’ bean pies and St. Ides in the same sentence”—a reference to Cube’s former ties to the Nation of Islam and his role as malt liquor pitchman. I’m not saying Common knocked Cube off his axis, but I am saying that Cube stuck to movies and songs like “We Be Clubbin’” for a while after this.

What’s this song’s legacy? “The Bitch in Yoo” first appeared on a Relativity Records compilation in 1996 and didn’t get much play beyond college radio and stray mixtape appearances early on. But it’s been surprisingly sticky in the three decades since—to the point where it’s now rightly considered one of the best diss tracks ever. (Partial credit goes to the Pete Rock beat.) But Common also gets credit for reinventing the “You haven’t made a good record since …” staple of rap beefs. Every one of those—from “one hot record every 10 year average” to Drake and Cole trying to discredit Kendrick’s recent output—owes a debt to “You ain’t made shit dope since AmeriKKKa’s Most.”

Was Common punching up or down—and does that matter? Way up! Before codifying cabbie-hat rap in the Soulquarians era, Common (née Common Sense) was an indie MC and Rap City staple best known for “I Used to Love H.E.R.,” a freshman-year-level creative-writing exercise that lamented how gangsta rappers—like Cube—had violated hip-hop’s, uh, “essence.” Cube, meanwhile, was a multiplatinum rapper who had annihilated his old N.W.A running mates with “No Vaseline” a few years earlier. It shouldn’t have been a fair fight, but “The Bitch in Yoo” lives on, while nobody thinks of the Westside Connection records that went at Common. But fittingly, both men ended up today where they probably belonged all along: better known as actors than for any beef record. —Sayles

19. “Back to Back,” Drake

Year: 2015

Target: Meek Mill

What’s the most vicious part of this song? The fact that Drake gave Meek less than two days to respond. There’s typically a “you go, I go, you go” tempo to rap battles, but Drake disrupted that and released a track that dealt Meek a critical hit at an unexpected time.

Though Meek released a half-baked response two weeks later, he’s since renewed his friendship with Drizzy and even kissed the proverbial ring onstage at one of Drake’s Philadelphia concerts. The bars were great, but more than anything, “Back to Back” proves that it’s best to attack when the enemy least expects it. It’s something Drake would learn the hard way nine years later.

What’s this song’s legacy? In the summer of 2015, Drake was basking in the afterglow of his greatest three-album run (Take Care, Nothing Was the Same, and If You’re Reading This It’s Too Late) and was well on his way to becoming hip-hop’s Thanos. Rap fans were preparing for Views, and the Canadian megastar appeared untouchable. Then came the ghostwriting allegations from Meek Mill.

For a moment, Drizzy was vulnerable. But within days, Aubrey released “Charged Up,” and in a swift, calculated move, he dropped “Back to Back” 48 hours after that.

The entire approach—from the bars (”This ain’t what she meant when she told you to open up more” stings as much today as it did on first listen) to the strategy—would’ve made Sun Tzu proud. With “Back to Back,” Drake diminished a peer’s credibility and parlayed an accusation of committing rap’s greatest sin into one of his biggest hits. It was the first diss track I ever heard in a club and represented one of the defining moments of Drake’s career.

Was this song a knockout blow? And then some. Not only did Drake belittle Meek’s career and clown his relationship with Nicki Minaj—both of which have since fallen by the wayside—but he proved that even his diss tracks could go multiplatinum and become club hits.

The same can’t be said for Mr. Twitter Fingers. One of my favorite stats from this beef: “Back to Back” has more Spotify streams than any Meek song outside of “Going Bad,” which features … Drake. For the record, can you immediately recall the name of Meek’s response track? —Comer

18. “Dollaz + Sense,” DJ Quik

Year: 1995

Target: MC Eiht

What’s the most vicious part of this song? Quik pulled back the curtains on their altercation at the airport (where Quik hilariously states he found Eiht “shakin’ like a crap game”), but one of the most clever shots at Eiht is Quik simply breaking down how Eiht spelled his rap moniker and the irony of one of “Compton’s Most Wanted” not even having a “g” in his name. “You left out the G ’cause the G ain’t in you”—what an effective way to call out someone’s gangsta (or lack thereof).

What’s this song’s legacy? In 1994, DJ Quik was tired of MC Eiht’s multiple diss tracks aimed at him, and when he was asked to submit a track to Death Row’s Murder Was the Case soundtrack, he sent “Dollaz + Sense,” which dissected everything about Eiht—from his subpar acting skills in Menace II Society to his small stature—over a G-funk trunk rattler.

Was this song a knockout blow? If Eiht had dropped out at that point, it would have been understandable, but no, Eiht and Quik battled for years after this track, finally squashing their beef in 1999. —khal

17. “Roxanne’s Revenge,” Roxanne Shanté

Year: 1984

Target: UTFO

What’s the most vicious part of this song? The fact that Roxanne was 14 years old when she recorded this and her song outlives any other record that came out of one of rap’s first—and easily its most protracted—major battles.

What’s this song’s legacy? You got an hour? Need a flowchart? This all starts with UTFO’s “Roxanne, Roxanne,” an early hit rap record about a girl who rebuffs the group’s advances. (Up to you to decide whether fictional Roxanne was right.) Shortly after that song’s release, UTFO canceled a show being thrown by DJ Mr. Magic and a then-unknown Marley Marl. Lolita Shanté Gooden—of course her name was Lolita—overheard Magic and Marley complaining about it outside the Queensbridge projects. She offered to take on the name Roxanne Shanté and make a song firing back at UTFO. “Roxanne’s Revenge” became a hit in its own right, launched the careers of Shanté and Marley Marl (and, in turn, arguably the Juice Crew), and over the next few years produced anywhere between 30 and 100 response records, depending on whom you ask. That includes ones by UTFO featuring a female rapper going by “The Real Roxanne,” but also ones from lesser-known fame-humpers writing from the perspective of fictional Roxanne’s parents, Roxanne’s doctor, and someone called “Ice Roxanne.” But maybe the most important response in the Roxanne Wars was “The Final Word—No More Roxanne (Please)” by the East Coast Crew. We may need the ECC to reunite for the Drake-Kendrick beef.

Who caught the worst stray? Too many records were pressed to truly say, but let’s go with the original “Real Roxanne,” who had to be replaced by Adelaida Martinez shortly after “The Real Roxanne” dropped. As with any good rap beef, “realness” is a moving goalpost. —Sayles

16. “Jack the Ripper,” LL Cool J

Year: 1988

Target: Kool Moe Dee

What’s the most vicious part of this song? When Kool Moe Dee initiated his beef with LL Cool J on the Teddy Riley–produced “How Ya Like Me Now,” his mistake was bringing synthesized saxophone sounds to an Ultimate Breaks and Beats fight. Initially released as the B-side to “Going Back to Cali” (both of which were produced by Rick Rubin), Cool J went hardcore on “Jack the Ripper,” embracing the more aggressive direction that rap was headed and essentially telling the old-school-tested MC to New Jack Swing on his nuts. Though Moe Dee was trying to burnish his career for a new era with “How Ya Like Me Now,” Cool J made it clear on “Jack the Ripper” that he was the fresh face of the genre and that his opponent was outdated.

What’s this song’s legacy? The knock on Cool J from everyone and their mama was that he was soft, trading on good looks and love songs to find fame. “Jack the Ripper’’ proved that he could still get pugnacious when he felt provoked, a tactic he returned to multiple times during his career. Its title was also referenced by both sides in Cool J’s subsequent beef with Canibus.

Was this song a knockout blow? The MCs traded several more disses over the years—including Moe Dee’s six-minute tirade “Death Blow”—but the fight was already over. LL Cool J remained a star and has become hip-hop’s goodwill ambassador, while Moe Dee’s profile dwindled. —Ducker

15. “Fuck Wit Dre Day (and Everybody’s Celebratin’),” Dr. Dre featuring Snoop Doggy Dogg

Year: 1992

Target: Eazy-E, Jerry Heller, Uncle Luke, Tim Dog

What’s the most vicious part of this song? “You fucked with me, now it’s a must that I fuck with you” is the perfect line to drop in such a vibrant diss record. If Eazy-E wasn’t mad before, everyone dancing to a hit record throwing all kinds of dirt on his name would have to have him pissed … right?

What’s this song’s legacy? When you talk about great diss songs also dominating the club, “Dre Day” is the record they are talking about. It’s hard to know what Eazy-E thought would happen when Dr. Dre finally released The Chronic, his long-awaited debut solo album, but it’s hard to believe that he thought Dre would turn “Atomic Dog” into a scathing diss that not only caught regular MTV rotation but also received gold-record status and hit no. 8 on the Billboard Hot 100 chart.

Was this song a knockout blow? Not necessarily. Sure, the video made Eazy-E look foolish, but as Eazy rapped on “Real Muthaphuckkin G’s,” Eazy was still making money off of Dr. Dre’s material at the time, literally getting paid while he was getting dissed. That’s a corporate win, but a win all the same. —khal

14. “Second Round K.O.,” Canibus

Year: 1998

Target: LL Cool J

What’s the most vicious part of this song? Canibus revisiting the tattoo on LL’s arm—the one that started this beef—and penning a witty sequence where, after ripping the mic from LL’s arm, he intimidates LL’s family enough to have them call Louis Farrakhan in an attempt to help squash their beef like he did for Common and Ice Cube.

What’s this song’s legacy? On LL Cool J’s seventh studio album, 1997’s Phenomenon, the Queens rapper brought in a bunch of rappers for the massive posse cut “4, 3, 2, 1,” including Method Man and Redman, Master P, and DMX. Also on the track was the rising mixtape star Canibus, who was asked to remove some fairly innocuous lines from his verse referring to the microphone tattoo on LL’s arm that LL interpreted as a diss. (LL would rewrite his own verse to throw Canibus shade on the song.) Canibus took those shots and, on his debut album, he retaliated with “Second Round K.O.” The song featured five minutes of Canibus threatening to rip said microphone from LL’s arm while Mike Tyson egged him on via phone. Oddly enough, the legacy of “Second Round K.O.” may be Canibus drilling the date of The Notorious B.I.G.’s death into every rap fan’s head.

Was this song a knockout blow? It’s hard to take out a hip-hop luminary like LL Cool J; Cool J responded with “The Ripper Strikes Back” and has continued to chart a career within Hollywood. —khal

13. “Drop a Gem on ’Em,” Mobb Deep

Year: 1996

Target: 2Pac

What’s the most vicious part of this song? Although neither Havoc nor Prodigy said Tupac’s name, both referenced the rumor that he was raped during his stint at Rikers Island. Prodigy took it a step further by mentioning the November 1994 shooting at Quad Studios in New York, which led to the bicoastal conflict that would overshadow the next two years.

“Rikers Island flashbacks of the house you got scuffed in / You would think that gettin’ your head shot’s enough, but then / Now you wanna go at my team, must have been drunk when you wrote that shit.”

What’s this song’s legacy? “Drop a Gem on ’Em” was Mobb Deep’s official response to Tupac’s vitriolic “Hit ’Em Up” and the first single from their forthcoming album Hell on Earth. Although they pulled it from the radio following his murder in September 1996 and eventually scrapped the plan to shoot a video out of respect for Tupac’s family, they still left it on Hell on Earth—which wasn’t released until two months later. And as dark as it may sound, Hell on Earth is a better album with “Drop a Gem on ’Em” included.

Was Mobb Deep punching up or down—and does that matter? Mobb Deep weren’t punching up as much as they were punching back following Tupac’s disrespectful tirade at the end of “Hit ’Em Up.” However, Tupac’s killing deflated the conflict just a few weeks after they engaged with him. —Kimble

12. “Nail in the Coffin” / ”The Sauce,” Eminem

Year: 2002

Target: Benzino

What’s the most vicious part of this song? Eminem borrows from the modus operandi of his archetype B-Rabbit from 8 Mile when he evokes images of his former wife cutting her wrists in front of him and his young child, before he actually begins digging into Benzino and his worst character flaws. Eminem then juxtaposes his life experience with that of a man who seemingly forces his seven-year-old son, Ray Ray, to be an entertainer in lieu of having a childhood. The line in question would prove far more prescient 20 years later, as Benzino’s younger daughter, Coi Leray, becomes a star in her own right. It seems Benzino has a habit of capitalizing on his kids.

What’s this song’s legacy? Benzino’s feud with Eminem is so integral to his legacy that it warrants its own subhead in the former Source co-owner’s surprisingly scant Wikipedia page. The whole ordeal ends with Benzino parting ways with The Source just two years later, saying he’d become too consumed with his feud with Eminem. He’s basically been a laughingstock ever since, unless you view being on Love & Hip-Hop: Atlanta as a great accomplishment.

Was Eminem punching up or down—and does that matter? On a technical rapping level, punching down. But the status that Benzino held as the head of The Source in the early 2000s cannot be overstated. This was the top-selling music magazine at one point. This was before streaming, when placement in a magazine like The Source or XXL could mean everything to your career. Benzino was, for better or for worse, one of the major tastemakers in hip-hop at the time. No one man should have all that power. Eminem was punching up, fighting against the oversized rule of a biased and greedy opportunist who exploited the magazine and also happened to make some of the worst rap known to man. —Morrison

11. “Checkmate,” Jadakiss

Year: 2005

Target: 50 Cent

What’s the most vicious part of this song? 50 Cent looked bulletproof at the time, especially going against someone as corny as Ja Rule. But if you put a magnifying glass to the Queens rapper, some things looked peculiar. Take “Ghetto Qu’ran,’’ his 2000 song that lays out the organizational depth charts of the infamous drug-dealing organization Supreme Team. It violated a rule of the streets: You don’t go around airing out business publicly—especially on wax.

“Checkmate,” the 50 Cent diss track by Yonkers rapper Jadakiss, throws away the magnifying glass and tosses 50’s offenses on a billboard. “I might never sell that much, but you can bet your last two quarters I’ll never tell that much,” claims Jada over a ruthless beat by the Alchemist. 50, who was quite possibly shot nine times in May 2000 over what he said in that song, had blown up by using his shooting to craft a self-mythology. He was the Luke Cage of rap: a bionically muscular warrior who had survived a bona fide assassination attempt—essentially unbreakable. Jadakiss shattered that—not only by making fun of his snitching, but by portraying 50 as a careerist who lacks a moral compass.

What’s this song’s legacy? 50 Cent came into rap like a hurricane—loud, explosive, and destructive. Jadakiss defeated him by reminding people that there was a reason why 50 was initially blackballed, that there was a reason real street dudes wanted him gone, and that the Queens rapper didn’t have all that much to rap about. 50 was making glorified pop songs at that point, coming off a disappointing sophomore slump. “Checkmate” could be considered the start of 50 Cent’s transition into a wrestling heel–like celebrity who used to be a rapper, not the street superhero he had portrayed himself as.

What’s your favorite behind-the-scenes thing about this song? 50 Cent purchased Mike Tyson’s mansion in Farmington, Connecticut, for $4.1 million in 2003. So when Jada says “you live in Connecticut,” he means in the monstrosity that Fif bought from Tyson, who once employed the man who allegedly shot him in Queens (as a bodyguard). —Buford

10. “How to Rob,” 50 Cent featuring the Madd Rapper

Year: 1999

Targets: Literally everyone

What’s the most vicious part of this song? While 50’s bars for Ghostface, Big Pun, and Jay-Z were enough to elicit responses from each of them, the most vicious bars come toward the end of the song. I can’t decide if accusing Kirk Franklin of robbing God’s people or highlighting Boyz II Men getting real-life robbed by their manager Michael Bivins is worse. But both feel like they cross the line from telling jokes to making things personal.

What’s this song’s legacy? 50 Cent’s “How to Rob” feels less like an attempt at a scathing diss record and more like an attempt at stand-up comedy. Referencing all the biggest names in rap and R&B in punch lines about sticking them up is quite the way to put yourself on the map, and it was the first step in establishing 50 Cent’s legacy as the ultimate troll and shit stirrer. Plenty of rappers have copied the formatting since.

Was 50 punching up or down—and does that matter? Obviously punching up. 50 had nothing to lose and everything to gain by mentioning all these artists on wax with hopes of getting someone to bite and getting his name out there. And the biggest of big fish bit when Jay-Z said, “I’m about a dollar, what the fuck is 50 Cents.” —Kermah

9. “Truth,” Gucci Mane

Year: 2012

Target: Young Jeezy

What’s the most vicious part of this song? 2012’s “Truth” is as evil as beef gets. Any rapper that claims “This is not a diss record” is a liar who’s about to go scorched earth, and “Truth” is Gucci Mane at his nastiest and most vindicated. Seven years after shooting and killing Jeezy affiliate Pookie Loc in what he’s maintained was an act of self-defense during a robbery—he was charged, but prosecutors eventually dropped the case—Guwop circles back for one last haunting laugh.

To this day, “Go dig your partner up, n—a, bet he can’t say shit” feels too real and personal to be committed to wax. Let’s not forget that this beef started over a song as goofy and infectious as “Icy.” There’s no reason Jeezy should’ve been rapping about putting a $10k bounty on Gucci’s chain, nor should there have been a home invasion that ended with someone dead and Gucci imprisoned for a short time. (Worth noting: Despite Pookie’s affiliation with Jeezy, the CTE World label head has repeatedly said he did not order the home invasion.)

A decade later, Gucci is a ripped health influencer, while Jeezy hosts talk shows and openly thirsts after Nia Long. It’s hard to fathom that the two pioneers of the trap movement would ever let it get this bad and ugly. Gucci ends his second verse by taunting Jeezy and claiming, “You left his son to be a bastard,” and it’s around then that you realize maybe Radric was right. This isn’t a “diss” song; it’s some other malevolent thing we still haven’t quantified.

What’s this song’s legacy? There’s no better way to demonstrate the flattening effect time has on beef than the moment Gucci played “Truth” in front of Jeezy during their tumultuous Verzuz. It’s one thing to tell a man to “dig [his] partner up” over an MP3; it’s another thing to say it to his face as thousands of people watch in real time.

But beef isn’t kind, and it rarely ages well. Death is just another part of the content equation. Two of Atlanta’s greatest took the Verzuz bread and smiled next to each other, despite years of bad blood, because what other option is there? No one starts beef to uphold morals, and that’s rarely why anyone stays in the rap game either.

Who caught the worst stray? Even by 2012 Lil’ Flip was already rendered a footnote in Southern rap history thanks to his beef with T.I., so it still seems like overkill for Gucci to rub a big heaping of salt in that wound one last time. (Sidenote: “Game Over” is still a banger.) —Holmes

8. “Real Muthaphuckkin G’s,” Eazy-E featuring Dresta and B.G. Knocc Out

Year: 1993

Target: Dr. Dre, Snoop Doggy Dogg, Death Row Records

What’s the most vicious part of this song? The line where the N.W.A mastermind taunts his former protégé about how “Dre Day only meant Eazy’s payday.” For much of the year that preceded the release of “Real Muthaphuckkin G’s,” the Ruthless Records founder suffered in silence as MTV played an endless loop of videos from The Chronic, operating as Death Row’s own Pravda for anti–Eazy E propaganda.

When Dre and Snoop Dogg finally dropped the video for “Fuck Wit Dre Day (And Everybody’s Celebratin’),” it seemed like the coup de grâce. The eviscerating parody of “Sleazy E” made Eric Wright seem scrawny, weak, and exploitative. Dre was Luke Skywalker vanquishing Darth Vader. But the empire that Dre helped build struck back.

“Real Muthaphuckkin G’s,” brought maniacal venom from the first seconds. Even Rhythm D’s beat was intended to be a sinister parody of Dre’s sound. The scraping noise that sounds like someone trying to escape from the gates of hell came from an old-fashioned metal washboard. Eazy and his new henchmen, B.G. Knocc Out and Dresta, hold nothing sacred. They roast Dre’s fake gangster image, his sexuality, the fact that the man who named his album after the era’s most potent strain of weed almost never actually smoked.

But the knockout blow arrived when Eric Wright undermined the very notion that he could ever really lose: “I had Dre signed as an exclusive producer and exclusive artist, so when Dre tried to make his deal all over at Interscope, I was included for the next six years,” Eazy-E said, describing his ultimate revenge to Arsenio Hall. “You can say all that you want to say. You can diss me all you want, but I’ma still get paid.” To add injury to insult, “Real Muthaphuckkin G’s” became the biggest hit of a double-platinum-selling EP, the most commercially successful solo project of Eazy E’s career.

What’s this song’s legacy? It may be the first meta diss in hip-hop history. Riffing on Dre’s “Sleazy E” lampoon, Eazy created his own effigy of Sleazy E, who is subsequently run out of Compton by a mob of the city’s biggest gangsters, all controlled by the CPT O.G.

In addition, Eazy E’s scorched-earth style of warfare—in which pictures from Dre’s past would haunt him—paved the way for Jay-Z to humiliate Prodigy at Summer Jam with childhood dance recital photos or for Pusha T to deploy the image of Drake in blackface.

If earlier rap disses largely stuck to tearing down a rival’s skills, Eazy E understood that gloves-off rawness was the essential part of his appeal. The carnivorous ferocity of 2Pac, Boosie Badazz, and even Kendrick Lamar first manifested in the form of this diminutive and sneering Compton Crip in locs and a Raiders hat.

Who caught the worst stray? Electro hip-hop. It’s not mentioned by name, but the photos of Dre wearing a stethoscope and sequin suit during his time with the World Class Wreckin’ Cru made it so that this integral chapter of L.A. hip-hop history was considered a laughingstock until well into the next decade. If it weren’t for “Real Muthaphuckkin G’s,” the Egyptian Lover and Arabian Prince would’ve inevitably received a critical rehabilitation much sooner. —Weiss

7. “Not Like Us,” Kendrick Lamar

Year: 2024

Target: Drake

What’s the most vicious part of the song? Kendrick may have just made the song of the summer—and one of the best diss records ever, full stop—while calling Drake a pedophile over a Mustard beat.

What’s this song’s legacy? This is the song that effectively ended the greatest rap beef in 20 years—and maybe the last great one ever. It came less than 24 hours after Kendrick and Drake traded songs in the waning hours of Friday: Drake went first with “Family Matters,” then Kendrick went nuclear with “Meet the Grahams.” While Kendrick’s track may be remembered as a cursed artifact—a six-minute open letter to Aubrey’s loved ones in which he says Drake deserves to die—it was maybe the most brilliant strategy ever deployed in a rap battle. Drake had just released what he believed to be the missile that would end this feud, and Kendrick shot it down with a nasty, hateful song over a crawling Alchemist beat. It completely neutralized any impact “Family Matters” could’ve had. It changed the narrative before the narrative took root. It committed the rumors that had been swirling about Drake for years to wax.

But it also killed the vibes. When Nas battled Jay-Z, he called him a “Tae Bo ho.” Kendrick, meanwhile, was calling Drake a Weinstein-level predator. How do you reckon with that?

Well, an instant hit record helps. About 20 hours after “Meet the Grahams,” Kendrick dropped “Not Like Us”—possibly the best club record he’s ever made, which is incidentally an ether-grade diss. Over a Mustard beat—and borrowing a flow popularized by Drakeo the Ruler, rest in peace—Kendrick builds on the backstory he laid out the previous day. “Freaky,” “69 God,” “OV-hoe”—by turning these barbs into call-and-response refrains, he used the playbook Drake used to beat Meek Mill nine years earlier and annihilated Drake. All that was left was the Notes app explanation, which functionally came the next night as Drake waved the white flag with “The Heart Part 6.”

Some people weren’t sure Kenny had the stomach for this when the whole thing started. Obviously, neither was Drake. Kendrick made fools out of a lot of folks, but only one had to release a song explaining that they were, in fact, not like Jeffrey Epstein.

Was this song a knockout blow? A fire can melt snow, but it’s got no chance against an avalanche. That’s effectively what it felt like watching “Family Matters” go up against this Kendrick onslaught. (Notice we’re not even discussing “Euphoria” or “6:16 in LA.”)

This thing is over. Kendrick’s legacy is secure. The only question now is what happens to Drake’s. —Sayles

6. “The Bridge Is Over,” Boogie Down Productions

Year: 1987

Target: MC Shan, Marley Marl, Queensbridge

What’s the most vicious part of this song? You’d be forgiven for thinking it’s the lyrical disrobing, the school-age insults that hit like chairs tossed at someone mid-gulp from a chocolate-milk carton, or even the acidic interweaving of taunting patois that give “The Bridge Is Over” its fangs. My contention, though, is that the coldest thing about the coldest diss track ever made are the keys in the background. Shit is ghoulish. Spectral footsteps. You hear that joint in the background and you run.

What’s this song’s legacy? “The Bridge Is Over” is the point of origin—the explosion of incomprehensible matter that created the rap beef universe as we know it. It is the first light, and if it is no longer the brightest, this is only because its progeny have marked so many vast and brutal galaxies in its image.

Was this song a knockout blow? One can quibble and say that the Bridge was not, in fact, over—that MC Shan’s biggest hit came well after the tussle—but the truth is Kris swung so hard on the Juice Crew that it took most of a decade for Queens to find another heartbeat. —Pryor

5. “The Story of Adidon,” Pusha T

Year: 2018

Target: Drake

What’s the most vicious part of this song? Weirdly enough the harshest bar on this massively vindictive song isn’t even about Drake! “OVO 40 hunched over like he 80 (tick, tick, tick!).”

What’s this song’s legacy? This song sent Drake into hiding for the summer. The whole summer! This song sent Drake crying to LeBron James, stammering and backpedaling about paternity tests, on some “what had happened was …” like he was a deadbeat dad on Maury. “The Story of Adidon” inflated the stakes of rap beef in a way that later generations—including Drake and Kendrick now—will have a hard time overcoming.

Was this song a knockout blow? This song was the textbook definition of a knockout blow. This song was somehow 100 times more humiliating than Drake’s own knockout blow against Meek Mill. This song had Drake binge-watching Grey’s Anatomy under the covers with his phone off for weeks on end, probably. —Charity

4. “Takeover,” Jay-Z

Year: 2001

Target: Nas, Prodigy

What’s the most vicious part of this song? Though Jay-Z debuted the first two verses (which included his excoriation of Prodigy, damning photograph and all) at Summer Jam 2001, the sharpest barbs were reserved for Nas on the final version. Following through on the promise he made at Summer Jam a few months prior (“Ask Nas, he don’t want it with Hov”), Jay called Nas a fraudulent observer, a foolish exploitee, and a has-been before the age of 28.

There were more clever bars, but his attempt to reduce Nas’s career to a lone standout moment that was rapidly fading from memory was a power move from the strongest force in hip-hop at the time.

“Four albums in 10 years, n—a? I could divide / That’s one every, let’s say two / Two of them shits was, doo / One was nah, the other was Illmatic / That’s a one hot album every 10-year average.”

On top of that, each interpolation of David Bowie’s “Fame” to punctuate an insult was salt in the wound. As disingenuous as it all might have been, it was a shrewd approach to attacking a foe—especially one you were a fan of.

What’s this song’s legacy? At the time, “Takeover” was arguably considered the ultimate display of Jay’s dominance. The unlikely superstar absorbed everything his challengers threw at him and returned fire with precision. In the context of The Blueprint, which many regard as his best work, it’s a flourish; he was dispatching people on a side mission.

To this day, “Takeover” is a clinic in using public opinion to your benefit. In a competition where the people ultimately decide the winner, the actual truth is far less important than what you can get those people to believe and repeat.

Sometimes—especially once you reach a certain position—the truth is what you tell people it is.

Was this song a knockout blow? Considering how efficient “Takeover” was, how Jay knew people would repeat whatever he said considering his standing, and the fact that it’s a well-crafted song, he created a nearly impossible deficit for Nas to come back from.

Funny how that worked out, though. —Kimble

3. “Ether,” Nas

Year: 2001

Target: Jay-Z

What’s the most vicious part of this song? “Oh, I get it: You Biggie and he’s Puffy.” While there are easily a dozen other lines that Nas delivers with more vitriol, it’s this aside, tucked toward the end of “Ether,” that pulls all of its threads to a single, humiliating pinpoint. The personal history—Jay-Z getting chased through cramped hallways, begging Nas for advice, wearing borrowed jewelry—collides with the portrait of Jay as an incorrigible biter and casts the empire he’d built as little more than a game of make-believe.

What’s this song’s legacy? What isn’t? The title itself became shorthand for a devastating blow to an artist’s reputation; it arguably coined “stan” as a term for an obsessive fan, swiping it from the Eminem song the year prior. Speaking of which, “Ether” was so instantly credible that it made the ridiculous notion of Jay getting washed on “Renegade” into conventional wisdom. He wasn’t; it didn’t matter. You can rank other diss songs higher than “Ether,” but this is the platonic ideal of the form.

Was Nas punching up or down—and does that matter? This is the sleight of hand. When Jay dropped “Takeover,” Nas’s career had already seemed to reach a nadir. After his planned third album, a sprawling double LP, was widely bootlegged, he rushed out a pair of records (I Am… and Nastradamus, both 1999) that were weighed down by half-hearted radio bids and soggy replacement material. Nas knew this: He describes himself on “Ether” as “left for dead” and places himself in a grave. Jay was massive, still expanding, becoming inevitable. But when Nas addresses him directly, the lines drip with condescension, smiling “like a proud dad” at all his success—before detailing the erosion of his values and the evaporation of his dignity. While Nas’s showing in the beef resurrected his career, it didn’t end his opponent’s: Jay only continued to amass wealth and cultural capital. But by the time the pair brokered a peace five years later, there was no ambiguity about what had gone down. —Thompson

2. “No Vaseline,” Ice Cube

Year: 1991

Target: Eazy-E, Dr. Dre, DJ Yella, MC Ren, Jerry Heller

What’s the most vicious part of this song? I’ll avoid listing all the homophobic and racial insults Cube tossed out—this is a rap battle, and particularly gnarly, so what do you expect?—and instead go with something more, uh, publishable. The refrain that opens the third verse—“I’ll never have dinner with the president,” a reference to Eazy-E accepting a luncheon invitation from the George H. W. Bush White House—is perhaps the most succinct “I’m real and they’re not” blow ever landed in a rap battle.

What’s this song’s legacy? Not many diss songs have become a pivotal moment in a hit movie. “No Vaseline” was the defining moment of the N.W.A-Ice Cube schism, which became the prototypical rap feud for a reason as old as the record industry itself: people getting fucked out of their money. It’s lived on because (1) it’s so nakedly vicious, (2) mostly everyone involved became wildly famous, and (3) it just flat-out bangs. But it also got another boost nine years ago thanks to the movie Straight Outta Compton, introducing new generations to Cube’s pantheon-level hating.

Was this song a knockout blow? Well, N.W.A never responded as a group, and Dre left shortly after “No Vaseline” dropped, citing the same types of monetary issues Cube laid bare here. If I’ve learned anything in 30 years of listening to hip-hop—and if we’re learning anything from watching Kendrick right now—it’s that you don’t mess with a pissed-off rapper from L.A. —Sayles

1. “Hit ’Em Up,” 2Pac

Year: 1996

Target: The Notorious B.I.G., Mobb Deep, Diddy, Junior M.A.F.I.A., Lil’ Kim, Chino XL

What’s the most vicious part of this song? Other than Faith Evans being dragged into it for allegedly sleeping with 2Pac, the shot at Mobb Deep’s Prodigy for suffering from sickle cell anemia was rather uncomfortable.

What’s this song’s legacy? The alpha and omega of diss tracks. On “Hit ’Em Up,” 2Pac boldly took diss songs to a place they’d never gone before, changing the art of the battle and the rap industry forever. If you’ve made it this far you certainly know the story by now: you’ve seen the movie, watched the documentary, read the book, and likely seen at least one of the hundreds of thousands of interviews breaking down every single millisecond of this song and the “beef” between Biggie and 2Pac. Hell, the phrase “keep it on wax”—something we hear every time a battle arises—was invented after this song dropped.

All of the elements of a great diss track are here, but Pac took it to new extremes on “Hit ’Em Up,” which reworked the beat of Junior M.A.F.I.A.’s “Get Money (Remix).” Pac took aim not only at his former friend the Notorious B.I.G. but also at Biggie’s wife, dragging her into the melee within the first second of the song. Other foes such as Puffy, Lil’ Cease, Lil’ Kim, Mobb Deep, Chino XL, and Bad Boy Records as a staff, record label, and as a motherfuckin’ crew caught headshots. Pac even had a music video featuring look-alikes of most of the aforementioned. The song didn’t just make waves culturally but also dominated the charts, shooting all the way to no. 1 on the Billboard Hot 100 for two weeks in the incredibly competitive summer of 1996 as part of the “How Do U Want It” / “California Love” maxi-single—the only place where you could hear “Hit ’Em Up.”

But bad news was around the corner, as the wake of “Hit ’Em Up” left two of hip-hop’s greatest artists dead in brutal killings that remain unsolved (at least officially) to this day. This battle will forever be a reminder that words can escalate quickly and turn deadly.

Who caught the worst stray? Faith Evans. But Chino XL comes in second place, as many fans didn’t know who he was at the time or why he was even mentioned. (Chino XL’s inclusion stems from a misinterpreted line on his song “Riiiot!”: “By this industry, I’m trying not to get fucked like 2Pac in jail.”)

What’s your favorite behind-the-scenes thing about this song? Goodie Mob arrived at the studio to visit 2Pac just as he’d finished recording “Hit ’Em Up.” They were the first people to hear the record outside of Pac’s camp. —Barber