Every actor or comedian had those roles in the past that were close to happening. For Dave Chappelle it was recently revealed that his was being eyed to star in 1995’s Clueless. Director of the teen film, Amy Heckerling shared in an interview with Vanity Fair that Chappelle almost played Stacey Dash’s love interest, which later went to actor Donald Faison.
Another future superstar surprisingly considered for a role in the beloved 1995 film was comedian Dave Chappelle. But the part of Murray — Cher’s best friend Dionne’s boyfriend — eventually went to Donald Faison. “I do remember that I saw Mel Brooks’ movie [Robin Hood: Men in Tights]. And I loved Dave Chappelle. I met with him in New York,” Heckerling recalls. “Donald had a much more kid-like energy. And Dave [had] a very cynical, grown-up, funny, comic kind of thing that I felt was maybe a little too edgy.”