Tag: What If

After growing up with Rob Reiner‘s movies playing on repeat in his home, Jake Szymanski recently got to explore the beloved filmmaker’s legacy in a unique way. Szymanski — the director of Jury Duty and Netflix’s forthcoming Cameron Diaz-led Bad Day — helmed the buzzy 2025 Super Bowl commercial that reunited Meg Ryan and Billy Crystal at Katz’s Delicatessen for the first time since they filmed their iconic scene in When Harry Met Sally.

“The best part for me was just getting to ask them questions and have them tell stories about making When Harry Met Sally and about Rob,” Szymanski tells The Hollywood Reporter. “He was very collaborative and let comedians do their thing, which I’m a huge believer in, and I don’t think I knew that’s what he was doing until later. Rob was able to make a movie that could only be his, while still letting comedic performers get their voice through.”

Hollywood continues to mourn the legendary figure and process the senseless tragedy of Reiner and wife Michele having been found dead Sunday in their Brentwood home. Loved ones and former colleagues have shared endless praise for the entertainer behind such other indelible favorites as This Is Spinal Tap, The Princess Bride and A Few Good Men. But even if they didn’t know him personally, Reiner’s impact endures for the industry’s top creatives through his storytelling and devotion to character.

“Movies like When Harry Met Sally and The Princess Bride are timeless because they’re built around people, not punchlines,” says Andy Jones, whose writing credits include It’s Always Sunny in Philadelphia. He points out that the dynamic between the When Harry Met Sally leads — a man (Crystal) and woman (Ryan) trying to remain platonic friends despite sexual tension — has continued to impact popular projects in recent years. This includes New Girl, the Fox comedy series that featured the will-they-won’t-they connection between Zooey Deschanel’s Jess and Jake Johnson’s Nick — and also saw Reiner portraying Jess’ father.

Adds Jones, “It was great to see Rob play Jess’ dad on New Girl because Nick and Jess have the same dynamic as Harry and Sally, or Gib and Alison in [Reiner’s 1985 comedy] The Sure Thing. It’s that brand of comedy that’s rooted in awkwardness, sincerity and people slowly realizing they care more than they planned to.”

One film that included direct acknowledgement of the joy from Reiner’s work was What If, the Daniel Radcliffe-Zoe Kazan romantic comedy that premiered at TIFF in 2013 and centers on two friends trying to ignore their romantic feelings. The movie includes references to When Harry Met Sally, and one scene involves the leads spotting each other at a screening of The Princess Bride.

Elan Mastai, who wrote What If, has heard that Reiner was very touched that the film wore its affections for his work on its sleeve. “When Harry Met Sally is my Godfather, and Princess Bride is my Star Wars,” Mastai, who earned an Emmy nomination for his work on This Is Us, admits with a laugh.

“It really strikes me just how rich the characters in these movies are, and you never feel like these are marionettes being put through the paces of a plot just to hit a punchline,” he continues. “These are fully fleshed-out characters, and the choices that they make, while hilarious, come from what makes these people tick — their wounds, their passions, their ambitions, their misguided beliefs. There’s such a deep empathy.”

While Reiner has been heralded for being somewhat genre-agnostic — given that his work includes thrillers, political comedies and quieter dramas — he will continue to be closely associated with the mockumentary thanks to his first directorial effort, This Is Spinal Tap, an eternal classic that spawned a sequel that hit theaters in September. Among those appreciating the impact of the 1984 original was the team behind American Vandal, the Netflix mockumentary series that satirized true-crime docs.

“In Spinal Tap, you see this idea that every idiot has a story that’s worth telling and worth seeing, and that’s such a lovely way to approach not just characters or comedy, but people in general,” says American Vandal writer Lauren Herstik. “If you talk to anyone who’s making a mockumentary, in the first breath, they’re going to say, ‘Spinal Tap — that’s the guiding light. That’s what we’re going for.’”

Szymanski, who directed Ryan and Crystal in the Super Bowl ad, grew up obsessing over The Princess Bride and Stand by Me but would later come to appreciate Spinal Tap. When he was working with the Lonely Island team on Saturday Night Live shorts and would then direct Andy Samberg in HBO’s sports mockumentaries Tour de Pharmacy and 7 Days in Hell, he found himself hoping to live up to such benchmarks as Reiner’s.

Says Szymanski, “Rob’s one of those filmmakers who — even though I never spent time with him — in a way, I owe a large part of my career to him because of his work on things like Spinal Tap.”