In a decision he would later regret, comedian Dave Chappelle turned down a role in Forrest Gump. At just 24, Chappelle was eager to take on the part of Kevin, Joe Fox’s business partner and dating advisor. Director Nora Ephron allowed Chappelle the freedom to improvise, and according to script supervisor Dreyer, “I don’t think there was anyone else on the list.” Chappelle’s performance was everything Ephron hoped for, as highlighted in the book I’ll Have What She’s Having.

Sara Ramirez had a memorable role as a cashier in the cash-only line at Zabar’s. This scene was inspired by a real event during the filming of Sleepless in Seattle when Ephron witnessed her first assistant director having a similar impact on an airport concierge. Interestingly, Zabar’s, the iconic grocery store, allowed a movie to film inside its premises for the first—and last—time during this production.

Not all New Yorkers were pleased with the disruption caused by the film’s production. During a scene shot at a restaurant on the Upper West Side, a local man began banging on the window, shouting at Ephron. “Nora Ephron! Nora Ephron! I thought you loved this neighborhood? Why are you f–kin’ with us?” cinematographer John Lindley recalled. Ephron managed to calm the man down eventually.

Chris Messina, who later gained fame playing Mindy Kaling’s love interest on The Mindy Project, had a small role in the film. He appeared as a clueless sales associate at Fox Books, needing Kathleen’s guidance on “The Shoe Books” series by Mary Noel Streatfield.

11. Chris Messina, who would go on to play Mindy Kaling‘s love interest (and the Internet’s boyfriend, Danny Castellano) on The Mindy Project, actually had a small role in the movie. He played the clueless sales associate working at Fox Books who needs Kathleen’s expertise when it came to “The Shoe Books” series by Mary Noel Streatfield.