Ben Stiller is not a standup comedian — and that’s OK.
At the 30th annual Nantucket Film Festival, Stiller assembled a group of comedy all-stars, as he has for the years, to discuss their journeys and share career insights while cracking up the auditorium audience.
This year, Stiller shared that he was “dead set against” a comedy career because it’s what his parents did, and an early attempt at standup in his teens pretty much killed that particular interest. The bit focused on New York City’s alternate side parking policy, and he even performed a version for festival-goers and his fellow panelists.
Obviously, comedy found its way to Stiller one way or another, but not on the path taken by the panel’s improvisers Amber Ruffin and Zach Cherry, or standups Iliza Schlesinger, Michael Ian Black, and Mae Martin. Schlesinger was working a desk job and asked her parents to help her buy a laptop for comedy writing; Martin dropped out of high school to work at Second City and tell jokes on stage; and Ruffin’s work led her to Chicago then Amsterdam.
The 2025 Nantucket Film Festival showcased over 50 feature and short films, including Jay Duplass’ “The Baltimorons,” A24’s “André is an Idiot,” Cole Webley’s “Omaha,” Kate Beecroft’s “East of Wall,” Matthew Shear’s “Fantasy Life,” Sophie Brooks’ “Oh, Hi!,” Heidi Ewing and Rachel Grady’s “Folktales,” and Kim A. Snyder’s “The Librarians,” among many others. The June 27 Screenwriters Tribute honored “Andor” creator Tony Gilroy, documentary director Alex Gibney, and “The Bear” co-showrunner Joanna Calo, who also participated in conversations and panels throughout the weekend.
The roundtable was moderated by writer and producer Donick Cary, a Nantucket native who took the stage at his high school alma mater for the conversation — and who, of course, couldn’t resist bringing up “Severance” to Stiller and Cherry before the event concluded. While the duo obviously couldn’t spill any secrets from Season 3, they talked about the show’s pockets of levity and Cherry’s freedom to improvise (a privilege not afforded to everyone on set).
“Anybody who’s done a series would know you start from one place, but then it’s going to develop and these things are going to happen that you don’t even know,” Stiller said. “You’re just locking in with the actors and saying ‘OK, we’re going to cast these actors, and it’s going to be a journey.’”