New Clueless behind-the-scenes secrets will blow your mind

Jun 10, 2015 at 7:14 p.m. ET
Image: Paramount Pictures

To celebrate Clueless' 20-year anniversary, Vanity Fair revealed a host of casting secrets, and you'll never guess which celebs were passed up for the leads.

It seems like every soon-to-be '90s A-lister was considered as an option.

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"I had my heart set on Alicia [Silverstone]," writer and director Amy Heckerling said in the article. "[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 the 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."

Fox casting director Carrie Frazier added some other huge names who were considered. "It was the first time I'd seen Angelina Jolie... but she was too knowing for what was needed for Clueless."

And that quote definitely made me laugh because Frazier is basically saying that Jolie wasn't clueless enough for Clueless.

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"Angelina never came in [to audition] for the project," Frazier continued. "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."

Everything happens for a reason!

But the list of A-listers who were considered for roles in Clueless hardly ends there.

"I met with Reese [Witherspoon] because everyone said, 'This girl's amazing. She's going to be huge,'" Heckerling recalls. This was a few years before Witherspoon landed her breakout role in Cruel Intentions. "I saw some movie where she 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."

More: Iggy Azalea as Cher Horowitz for Clueless-inspired "Fancy" music video

As for the role of Josh that eventually went to Paul Rudd, "I brought in Ben Affleck, "Frazier said. "I thought he would be fabulous for it. I was really trying to get Ben Affleck the part."

Maybe it's because Rudd is too ingrained in my mind, but I just can't see Affleck in the role.

Heckerling admits Josh was the hardest role to cast.

"I'm fairly sure Zach Braff read for Josh," Paramount Pictures casting director Marcia Ross revealed. "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. 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."

Other actors who were up for parts: Terrence Howard auditioned against Donald Faison for the role of Murray. Producers really wanted Sarah Michelle Gellar for the role of Amber but her contract with All My Children at the time wouldn't allow it in her schedule. Brittany Murphy was brought in as a potential Cher but was eventually cast perfectly as Tai. And Seth Green was one of the top picks to play Travis.

Which could-have-been Clueless actor surprises you the most?