20 Things You Didn't Know About Clueless
19. All Of These Actresses Were Considered To Play Cher
The character of Cher Horowitz being a strong female lead as she is, a large number of up-and-coming actresses either auditioned for or were considered for the role.
Before Alicia Silverstone won the part - without even having an audition, no less - the likes of Reese Witherspoon, Zooey Deschanel, Alicia Witt, Keri Russell, and Tiffani Thiessen all met with Amy Heckerling to discuss playing Cher.
Angelina Jolie and Gwyneth Paltrow were also both considered, though neither ultimately auditioned.
In the end it's incredibly difficult to imagine anyone but Silverstone in the role, but of the aforementioned actresses, Reese Witherspoon surely seems like the most natural fit.