Clueless, Reese Witherspoon, Alicia Silverstone, Angelina Jolie

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In honor of the 20-year anniversary of Clueless (yes, 20, can you believe it?!) Vanity Fair has published an amazing feature which spills loads of behind the scenes secrets from the iconic flick. 

Appropriately titled, "The Definitive Oral History of How Clueless Became an Iconic 90s Classic," the article features interviews with a number of the key players in the making of the film, including director and writer Amy Heckerling, Carrie Frazier, Marcia Cross (the casting directors at Fox and Paramount, respectively) as well as stars Alicia Silverstone (Cher), Stacey Dash (Dionne) and Paul Rudd (Josh).

If you're a Clueless fan, the entire piece is worth a read, but the part about the casting process is particularly fascinating as it reveals that nearly every major Hollywood actress auditioned for the role of Cher!

"I had my heart set on Alicia [Silverstone]" Heckerling recalls. "[But] Fox … wanted me to explore all the [options]…. I saw Alicia Witt, the redheaded [actress]. And who else? Tiffani Thiessen. The one that—she was in that show and she cut her hair and everybody was mad? Keri Russell, yes. Then they go, 'You've got to see the girl in [Flesh and Bone].' I never got to see her. I guess she was off on other things. That turned out to be Gwyneth Paltrow."

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Paul Rudd, Alicia Silverstone, Clueless

Paramount Pictures

Gwyneth Paltrow as Cher Horowitz?! Now that's something we'd love to see. 

"It was the first time I'd seen Angelina Jolie…. But she was too knowing for what was needed for Clueless," Frazier continues. "Angelina never came in [to audition] for the project. I was just looking at her tape. I remember an agent pitching her, and I'm going, 'No, no, no, this is exactly the opposite of what I need for this.' Later on, when I started heading up the casting department for HBO, and I got the script for Gia, I said, 'I've got the girl.' That was Angelina." 

(Safe to say the role was a better fit). 

As for the other now-A-list actresses who were up for the part? 

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Brittany Murphy, Stacey Dash, Alicia Silverstone, Clueless

Paramount Pictures

"I met with Reese [Witherspoon] because everyone said, 'This girl's amazing. She's going to be huge,'" Heckerling says of Witherspoon, who just a few years later, would land her breakout role in Cruel Intentions.

"I had [Amy] meet Reese over at the Four Seasons hotel in Los Angeles, on Doheny, in the bar," Frazier adds before Heckerline recalls, "I saw some movie where she [Witherspoon] had a southern accent. Maybe it was on TV, a movie of the week. But I did see some scenes of hers and went: Wow. She's amazing. But Alicia is Cher." 

When it came to the role of Josh, who was brilliantly played by actor Paul Rudd, the list of thesps who auditioned for the part is, again, quite shocking. 

"I brought in Ben Affleck, for the role of Josh," Frazier reveals. "I thought he would be fabulous for it. I was really trying to get Ben Affleck the part." 

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Clueless Gif

Additionally, Frazier says she "brought in [Brittany] Murphy. She was just so similar, again, to the character. She was really sweet."

However, Marcia Cross became the new casting director when the project moved to Paramount, and she was ultimately responsible for casting Rudd. 

"Because I was always reading actors, I knew a lot of young actors, and I was able to come up with a bunch of thoughts for parts and sort of come in with ideas and show her [Amy Heckerling]," Cross says. "Paul Rudd was one of those people."

As Heckerling recalls, casting Josh "was the hardest" and he was actually turned down for the role until eventually, he was brought back into the casting mix. 

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Clueless Gif

"I'm fairly sure Zach Braff read for Josh," Cross reveals. "I had hired a casting director in Chicago to put people on tape for the role while I was still searching for an actor to play the role. He was going to [Northwestern] at the time. My note was that he was good.

"We screen-tested several guys with [Alicia] on film, and she and Paul—he really was good with her," she continues. "From the minute he came in to the minute he got the part—and it was such a long journey, really, that one in particular—there was always this sort of harking back to: remember Paul? I can't explain it to you. He never went out of consciousness." 

As for Rudd's reaction? 

"I don't remember the actual call saying I got the part…. I wasn't sure about [Halloween]," he recalls of his first film. "But Clueless: no, I wanted to do that one."

For more on Clueless—including how Terrence Howard almost got the role of Murray (played by Donald Faison)—be sure to head to Vanity Fair!

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