Director Amy Heckerling met with Alicia Witt, Reese Witherspoon, Keri Russell, and Tiffani Thiessen for the role of Cher. Angelina Jolie and Gwyneth Paltrow were both considered for the role, but neither auditioned. Ben Affleck and Zach Braff both auditioned for Josh. Seth Green auditioned for Travis. Alanna Ubach auditioned for Tai. Terrence Howard auditioned for Murray, while Dave Chappelle also met with Heckerling to discuss the role. Jamie Walters auditioned for Christian. Sarah Michelle Gellar was offered the role of Amber, but had to turn it down when her soap opera La valle dei pini (1970) refused to allow her time away. Jerry Orbach was offered the role of Mel Horowitz, but similarly could not get time away from his show, Law & Order - I due volti della giustizia (1990), while Harvey Keitel was deemed too expensive to be cast in the part.

Film

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