'Clueless' Almost Starred Angelina Jolie, And Every Other Actor You Love

You’d be justified in thinking "As if!," but according to Jen Chaney’s new oral history of Clueless, Jolie auditioned for the role - as did Reese Witherspoon, Keri Russell, Tiffani Amber Thiessen, and Alicia Witt.

In a Vanity Fair excerpt from the book, director Amy Heckerling reveals why she picked Silverstone to play Cher, the fashion-obsessed teenage matchmaker at the heart of the beloved 1995 high-school comedy.

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"I was watching an Aerosmith video of Cryin'. That was the first video she was in. And I just fell in love with her,” says Heckerling. “Then my friend [casting director] Carrie Frazier said, ‘You have to see this girl in The Crush.’ And I was like, ‘No, I want the Aerosmith girl.’ Well, it was the same girl.”

As soon as Silverstone auditioned, Heckerling knew her instincts were right. But to placate the studio, she and Frazier saw other actresses.

One was Jolie, who submitted an audition tape, but was never really a contender. (“She was too knowing for what was needed for Clueless,” says Frazier, who later cast Jolie in HBO’s Gia.) Witherspoon, who met Heckerling for lunch to discuss the role, had a better shot. (“I did see some scenes of hers and went: Wow. She’s amazing. But Alicia is Cher,” says the director.)

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The studio also advised Heckerling to look at a rising actress in a movie called Flesh and Bone.

“I never got to see her. I guess she was off on other things. That turned out to be Gwyneth Paltrow,” Heckerling says.

In the end, Heckerling got her first choice: Silverstone, whom she loved from the moment she auditioned. “She was like 17, and she was just so adorable and sweet and really innocent,” the director recalls.

A few other casting tidbits from the Clueless oral history:

Paul Rudd was one of the first actors to audition for the role of Josh, Cher’s environmentally conscious ex-stepbrother. The producers waffled on casting him, so he took a part in Halloween: The Curse of Michael Myers instead. After auditioning other actors, including Ben Affleck and Zach Braff, the Clueless team came back to Rudd — who was by that time done with Halloween.

Breckin Meyer competed for the role of stoner Travis with his real-life best friend Seth Green.

The late Brittany Murphy nailed her audition for the part of new-in-school misfit Tai. “When she came in, it was just like: Oh my God. Stop the press. This is the girl,” recalls Alicia Silverstone.

Donald Faison beat out his childhood friend Terrence Howard for the role of Murray, longtime boyfriend of Dionne (Stacey Dash). Heckerling also considered Dave Chappelle, because she loved his performance in Robin Hood: Men in Tights. “Donald had a much more kid-like energy,” Heckerling says of her final choice. “And Dave [had] a very cynical, grown-up, funny, comic kind of thing that I felt was maybe a little too edgy.”

Sarah Michelle Gellar was the top choice to play Cher’s bratty rival Amber, but she couldn’t change her shooting schedule for the soap opera All My Children. The role went instead to Elisa Donovan.

Read the full Vanity Fair article here.

Gwynne Watkins writes for Yahoo Movies