“There’s a long list of almost-weres in the history of Clueless casting. For the role of Cher...Reese Witherspoon, Angelina Jolie and Sarah Michelle Gellar were considered—about Jolie, casting director Carrie Frasier says: ‘No, no, no, this is exactly the opposite of what I need for this.’” An Oral History of Clueless

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I actually think Reese Witherspoon would have been a passable choice. The others? Nope. Alicia Silverstone still wins, though.