Vanity Fair has just given us a giant 90s present in the form of an epic oral history from the cast and creators of Clueless. You should definitely give the whole thing a read, but as a taste, at one point Amy Heckerling and the movie’s casting director Carrie Frazier go into some alternate casting choices that almost were. Here are some bizarro world versions of Clueless that almost existed.
Amy Heckerling was set on Alicia Silverstone, but the studio wasn’t so sure and made her look at:
Reese Witherspoon was probably the top contender, if Heckerling hadn’t been so adament about Silverstone.
Angelina Jolie was considered “too knowing” for Cher.
Zach Braff was still a student at Northwestern when he auditioned.
Ben Affleck - The studio was pushing Ben Affleck HARD.
Dave Chappelle was a major contender, but was ultimately deemed “too edgy” for Murray.
Sarah Michelle Gellar was offered the part, but All My Children wouldn’t let her off for filming.
Seth Green and Breckin Meyer were real life BFFs and the final two picks for the role.
Alanna Ubach was Seth Green’s real-life girlfriend at the time.
Jerry Orbach was offered the role
Harvey Keitel - They wanted but “couldn’t afford” Keitel.
From Vanity Fair.