Internet personality, one half of the “Las Culturistas” podcast and the prince of pop culture himself Matt Rogers heads to the City Beautiful to deliver a heaping helping of holiday laughs.
In what Rogers called the “dumbest, gayest Christmas spectacle you can imagine,” his annual holiday tour Christmas in December blends comedic sketches, satire and plenty of campy live music.
We’ll likely hear tunes from his own 2022 musical special, Have You Heard of Christmas?, get first listens of new songs and witness some Mariah Carey high-note levels of Christmas cheer.
The project started in 2017, Rogers told Billboard, in a 70-seat cabaret theater in New York City. It’s since grown to fill several thousand-capped rooms of fans, including its very last stop right here in Orlando. Get ready to ho ho ho.
6:30 p.m. Sunday, Dec. 21, Plaza Live, 425 N. Bumby Ave., plazaliveorlando.org, $63-$86.
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Cosplay, anime panels, voice actor meet-and-greets, vendors, gaming and themed dances
Four-time Emmy- and Grammy-nominated comedian, singer and internet sensation Randy Rainbow brings his sharp wit and show-stopping vocals to Orlando this weekend.
Renowned for his musical parodies and timely political satire, Rainbow’s live show blends comedy, music and audience interaction for a theatrical evening.
Expect the rapid-fire commentary and signature charm that’s made him a favorite among fans of both Broadway and late-night humor.
8 p.m. Saturday, Oct. 25, Hard Rock Live, 6050 Universal Blvd., hardrock.com, $36-$86 .
A young Preacher Lawson doing stand-up at Austin’s Credit: rCourtesy Preacher Lawson
For two decades, Sunday night at Austin’s Coffee was where Orlando comics tested material, bombed gloriously and became family. When the coffee shop and creative haven was forced to move, comedian Preacher Lawson stepped in to help keep that Sunday tradition alive.
“I’m really a silent investor. I don’t run the business,” says Lawson, who earned his comedy chops in Orlando and broke out nationally on America’s Got Talent, to Orlando Weekly. “My business was just to make sure that this place doesn’t get shut down, because it’s the longest-running mic in Orlando.”
That’s the short version of a story that has played out since 2021, when the City of Winter Park made it known it wished to buy the land at 929–957 W. Fairbanks Ave. for an intersection and drainage project. The purchase went through in late 2024, and with its lease set to expire October 31, 2025, Austin’s had to act. Fast.
Friends of Austin’s Coffee rose to the occasion and brought in funds. Siblings Angela Whitmer and Richard Whitmer came in as co-owners, and Lawson joined them following an early-August Hail Mary call from the savvy comedy mic mainstay Craig Norberg, who had an inkling Lawson might be game.
“Even when he was famous, he would always come in for open mics when he was in town,” says Norberg. “I knew he wanted it to succeed, so I told him what was going on.”
Norberg founded the mic the same year Austin’s opened, 2003. “I had been doing comedy for about a year or less,” he says. “I wanted more stage time for myself and the community. I really had no idea what I was doing, but I figured it was worth a shot.”
Intrepid comedy fan and supporter Jean Anderson first checked out Orlando comedy in 2005 or 2006. “I started going to Austin’s. That’s where I first saw Pat Garrity. He was pretty impressive. And later on, Preacher was there. He stood out right away,” she recalls.
“When I first came up, they showed me a lot of love,” says Lawson. “The owner knew my drink. It was an Arctic Thunder, basically chocolate milk, and I’d get it every Sunday. They’d see me walk in and just know. It’s been an important place in my life for a lot of reasons. It was the first place I performed after my breakup. It was the first place I went after being on TV. The first time I felt like I really killed on stage was there. I went up to do three minutes and ended up doing 10.”
Dewayne Williams first braved the mic in 2012 and became a regular in 2017. “Austin’s played a big role in my career because it gave me stage time,” he says. “It’s a different energy from anywhere else in the city. The crowd is mostly college kids. A lot of them haven’t lived through the things you’re talking about, so getting them to relate is a challenge. It was a fun challenge because the goal is the same. Make them laugh.”
From the start, Norberg wanted Austin’s to be what it in fact became, a home base for comedians.
“The first night I went, I didn’t even perform. I just hung out,” says Edwin Pagan. “Akeem Woods was guest hosting, and Heather Shaw, Justin Lawson and Ryan Holmes were around. I went back the next Sunday and finally went up. I don’t even remember how it went. At some point you stop caring about bombing; you’re just happy to be up there. Where else are you gonna do comedy on a Sunday?”
“The real magic was outside after midnight, with everyone just hanging out and talking. There wasn’t much drinking, so it was chill. That’s how I met people I’m still close with. Austin’s was social glue for comics in this city.”
Lawson sees it similarly. “Austin’s is a judgment-free zone. You could do whatever you wanted as long as you didn’t hurt anyone, and nobody cared. It’s weird in the best way, like family. You’ve got people you love, people you argue with, people you miss. It’s all family.”
Comedian Robin Love has been a regular at the mic, considering it a mainstay.
“We all keep coming back for something and at the end of the day, that’s what makes it beautiful,” she says.
On Sunday, Oct. 19, the comedy family gathered at the familiar building on Fairbanks for the last time. “It felt different,” Pagan says. “You saw all the comics you started with, all the old faces. It wasn’t a funeral; it was like a reunion. You realize how far everyone’s come, and you still have that respect for each other.”
“I have so many memories. I was crying. It’s just moving, and it’s good, but I’m still sad. I don’t know why,” says Love.
Now the good news: 2240 W. Fairbanks Ave., formerly Loving Vegan Market & Cuisine in Winter Park, is the confirmed new residence of this town’s favorite coffee, comedy and open mic haunt. And likely within weeks, said two insider sources, Austin’s will reopen.
“I’m excited for the new spot,” Williams says. “The longest-running open mic in Orlando gets to continue in a new location. New building, same night, same energy or better.”
Oliver Morris and Casey Tregeagle in “Nosferatu” at The Ren (2024) Credit: Rachel Dresner
Whether your Halloween decorations have been up for weeks or you’ve been waiting patiently for that calendar page to turn, the time has come: Fall is here. So go ahead and start marking your calendar with all of the below dates, our picks for what we are somewhat arbitrarily defining as fall in Orlando — Oct. 1 through Nov. 11, or in other words, all the weeks between this, our Fall Guide, and the arrival of our Holiday Guide Wednesday, Nov. 12. — Pumpkin spicily yours, the OW editorial team.
???: Nosferatu
This is a sentimental pick for us, even through — as we type this — the Renaissance Theatre Co.’s immersive annual vampire extravaganza is on unexpected and unwelcome hiatus. The theater space has been shut down by the city after a surprise inspection revealed code violations, and there’s no clear timeline for reopening. And that sucks (wink wink) because Nosferatu is a dazzling, elegantly staged, carnal and campy delight year after year. For now, you can donate to the Ren directly or check out sister event V Bar as it haunts different venues around town like Plaza Live.
Saturday, Oct. 11: Leslie Jones
“Things are dark, but I want to give people a reason to laugh instead of cry,” says comedian and television star Leslie Jones. You know her from Saturday Night Live, the Ghostbusters reboot, her singular Olympics commentary, guest spots on The Daily Show, Supermarket Sweep v.2, or even her podcast “The Fckry” and now you can see her in person at the Plaza Live. Her comedy is audacious, unapologetic, topical and perfectly suited for the moment. 8 p.m., Plaza Live, 425 N. Bumby Ave., plazaliveorlando.org, $66-$178.
Oct. 11-12: Winter Park Autumn Art Festival
Celebrate local arts this fall at the 52nd Annual Winter Park Autumn Art Festival, the only juried fine art festival exclusively featuring Florida artists. Hosted by the Winter Park Chamber of Commerce, this weekender transforms Central Park into an outdoor gallery. Attendees can also enjoy live music, local entertainment, children’s activities and a welcoming festival atmosphere. Central Park, 251 S. Park Ave., Winter Park, winterpark.org, free.
Sunday, Oct. 12: Rocky Horror Picture Show 50th Anniversary
Oh Rocky, has the Dr. Phil got a shadowcast for you. To mark a half-century of the seminal, genderfluid, glammy midnight monster musical, Rocky Horror Picture Show screens at our most lavish downtown venue. Probably no rice-throwing during this one, but to make up for it, special guests from the film will be in the castle: Barry “Brad” Bostwick, along with accidental gothic style icons Nell “Columbia” Campbell and Patricia “Magenta” Quinn. VIP meet-and-greets seem essential. 7:30 p.m., Walt Disney Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave., drphillipscenter.org, $46-$300.
Tuesday, Oct. 14: We Wiggle Dolls: A DIY Puppet Cabaret (For Adults)
Brooklyn-born “DIY puppet cabaret” (go onnnnnn) We Wiggle Dolls comes to Conduit as part of a fall tour that promises to upend your notions of puppetry in the same way Miss Pussycat, Poncili Creacion and The Vourdalak did. We Wiggle Dolls push the art form forward, both technically — techniques and construction — and, obviously, thematically, as a more grown-up endeavor. Featuring on the night will be Naughty Little No Good, Puppet Parts Productions, Yellowlemonshapedrock and Chaz Lord from Drippy Eye Projections. You should enter this with no expectations. We certainly are …. 7 p.m., Conduit, 6700 Aloma Ave., Winter Park, conduitfl.com, $19.90.
Downtown Arts District hosts the annual Dia de Los Muertos & Monster Party Credit: courtesy image
Thursday, Oct. 16: Día de los Muertos & Monster Party
Downtown Art District’s spooky arts party returns with the 16th Annual Día de los Muertos and Monster Party at CityArts. The evening opens with two dynamic exhibitions: a Día de los Muertos showcase featuring traditional ofrendas and catrina dolls, and a monster-inspired gallery of spooky art by local and international artists. Outside on Pine Street, the festivities spill into a lively block party with food, drinks, entertainment and vendors. A frighteningly good time for all. 6 p.m., CityArts Orlando, 39 S. Magnolia Ave., downtownartsdistrict.com/ddlm, free.
Orlando Ballet kicks off their 2025/2026 season with a double dose of classic Tchaikovsky chestnuts. Of course The Nutcracker will dance in the winter holiday season, but starting things off this fall is the romantic Russian composer’s elegant and lovelorn Swan Lake, featuring choreography by Christopher Stowell and live scoring from the Orlando Philharmonic. Past productions of this iconic heartbreaker have never failed to impress, so expectations are high. Steinmetz Hall, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave., drphillipscenter.org, $43-$200.
Spooky Empire (2024) Credit: Matt Keller Lehman
Oct. 31-Nov. 2: Spooky Empire
Alongside the likes of Halloween Horror Nights, Phantasmagoria and Nosferatu, one of the ghoulish gems in Orlando’s Halloween crown has to be Spooky Empire. This horror-focused fandom fest provides hearty attendees with cosplay, vendors, panels and film screenings by the metric ton. But this year — and we really mean it this time — is all about the celebrity guests. It’s a terrifying bonanza with the likes of Elvira, Parker Posey, David “Art the Clown” Thornton, Chris Jericho, Method Man, Bill Moseley, Tom Savini, Nivek Ogre from Skinny Puppy, several Jasons, the cast of It, Frank from Hellraiser … we could go on, but go see for yourself (if you dare). Hyatt Regency Orlando, 9801 International Drive, spookyempire.com, $40-$299.
Sunday, Nov. 1: Beer Bacon & BBQ
Altamonte becomes the promised land for carnivores as the Beer Bacon & BBQ Festival sizzles. The name pretty much says it all; the focus is squarely on the array of roughly 40 craft beers ready for quaffing as well as meaty decadence of the bacon and barbecue (or both!) varieties proffered by local spots like Smoke in the City BBQ, Phat Ash Bakes, Big John’s Rockin’ BBQ, Heart and Soul Food Truck and more. There will be live music and games, but you might be too blissed out in a porky food coma-slash-nirvana. 2 p.m., Cranes Roost Park, 274 Cranes Roost Blvd., Altamonte Springs, beerbaconandbbq.com, $41.93.
Wednesday, Nov. 5: Doug Stanhope
Amid the bounty of righteous comedic anger we’ve got headed our way this fall, Doug Stanhope stands tall as perhaps the one radiating the most confrontational fury. Stanhope, like a latter-day Bill Hicks, is not afraid to alienate — or maybe provoke thought — as he rails against the fractured American way, clad in a rumpled thrift-store suit like a crooner with nothing to lose, with maybe a dash or two of Howard Beale for spice. 6 p.m., Funny Bone, 9101 International Drive, orlando.funnybone.com, $54-$84.
Jonathan Van Ness Credit: courtesy image
Saturday, Nov. 8: Jonathan Van Ness
Queer Eye star and ethereal delight Jonathan Van Ness is setting out on another leg of their “Hot & Healed” stand-up tour, on the fashionable heels of the release of their debut comedy special, Fun & Slutty. Van Ness promises a new and different take from what fans saw on Fun, considering the bleak current sociopolitical landscape. “It’s a lot of Republican stuff. It’s a lot of trans commentary on living as a gender-nonconforming person in this time,” Van Ness told GLAAD, describing their new material. “I’m also dealing more with racism than I ever have … white people … honey … we got to talk about it.” 8 p.m., Hard Rock Live, 6050 Universal Blvd., entertainment.hardrock.com, $48-$142.
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Hayrides, apple cider, themed treats, photo ops and even dog costume contests are popping up all around town
Drag, music, art, meditation, Doug Rhodehamel!
Plus Red Panda Noodle and Phat Ash Bakes move into downtown food truck park at Art2
Jordan Klepper and Roy Wood Jr. come to Orlando for some serious comedy
Daily Show stars and comedic firebrands Jordan Klepper and Roy Wood Jr. are teaming up to say hello/goodbye to “America, for the Last Time” in December.
Billed cheekily as “a comedic town hall that digs into the issues that matter and many that do not,” Wood and Klepper are taking their show on the road to just two cities [so far announced] in this newest leg of their duo tour: Brooklyn in November and Orlando in December. A Q&A portion of the evening is tantalizingly hinted at.
Both are longtime Daily Show correspondents who have branched out into a multiplicity of solo endeavors — stand-up tours, documentaries and solo specials. And both embody deadpan [Klepper] and exasperated [Wood Jr.] humor like few others.
“America, for the Last Time” comes to the Walt Disney Theater at the Dr. Phillips Center on Dec. 7. Tickets are on sale through the venue.
Comedian Marlon Wayans plays Orlando for three nights
White Chicks and Scary Movie star, In Living Color trailblazer and renowned stand-up Marlon Wayans performs at the Funny Bone for a three-night stand this weekend.
Picking up where he left off after a strong performance at UCF’s Homecoming Comedy Night in 2022, this comedian finds humor and heaviness in topics of acceptance and grief, making you laugh about experiences you didn’t know you could laugh about.
One of Wayans’ latest specials, Marlon Wayans: Good Grief, includes very affecting material about acceptance of his transgender son and other family-related humor. Pregame with the aforementioned Amazon Prime special and get ready to witness a key part of one of America’s first families of comedy.
Thursday-Saturday, June 13-15, Funny Bone Comedy Club, 9101 International Drive, orlando. funnybone.com, $54-$84.
