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Way Harsh, Tai - Guess Who Almost Got The Lead In 'Clueless' 20 Years Ago?

We were *this* close to rolling with a whole different set of homies.

It's been 20 years since "Clueless" kids were inspiring us all to slip on a pair of knee-high stockings and play matchmaker with the single teachers on staff. Yes even.

And though Alicia Silverstone is adorably etched in your brain as the face of Cher Horowitz -- that is, unless you got into the TV show, too, in which case you might also have a little Rachel Blanchard in the mental picture mix -- there was another then-on-the-rise young actress who almost nabbed the role of the skimpy Calvin Klein "dress"-clad princess of Beverly Hills.

In honor of the film's anniversary, writer-director Amy Heckerling revealed to Vanity Fair a whole list of would-be Chers who were in the running to portray the ditzy-but-glitzy dame -- and one who almost had it in the bag.

Can you imagine any of them in the role? We chose some throwback photos for each just to be totally fair ... as if! We're, like, totally buggin' about the very idea.

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    Heckerling revealed, "I had my heart set on Alicia [Silverstone, but] Fox wanted me to explore all the [options]. I saw Alicia Witt, the redheaded [actress]."

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    The "Saved By The Bell" star was also in the mix. But the brunette beauty had no trouble moving on to another high society L.A.-centric phenom with "Beverly Hills, 90210."

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    And before she was the lead in "Felicity," Keri Russell was also a contender for the part. "The one that—she was in that show and she cut her hair and everybody was mad? Keri Russell, yes," remembered Heckerling.

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    Though she never actually auditioned for the role, the studio had their sights set on Gwyneth Paltrow for the part. "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." (Fun fact: Goop starred in "Emma" the very next year -- which is relevant because "Clueless" was also based on the same Jane Austen novel. How about that for a sliding doors moment?)

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    At the time, Angelina Jolie was still making her way into somebody status by way of her gritty breakout role in "Hackers," but casting director Carrie Frazier remembers watching her film in consideration for the role -- an encounter that would later set Angie up with the role that would really jump-start her career in movies. "It was the first time I'd seen Angelina Jolie," said Frazier. "But she was too knowing for what was needed for 'Clueless.' 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."

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    Turns out, Reese Witherspoon was almost the girl for the job. "I met with Reese because everyone said, 'This girl's amazing. She's going to be huge,'" explained Amy Heckerling. "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."

On a related note, Heckerling almost didn't pick Paul Rudd for the part of the adorkably lovable step-brother-turned-heartthrob Josh.

"I had a vision in my head and it wasn’t jelling with people out there. When I’m writing, I usually have little pictures of what I imagine the guy looking like. And I had the Beastie Boy: Adam Horovitz. There was something smart and funny about him," she said.

Meanwhile, Frazier had her heart set on Ben Affleck. "I brought in Ben Affleck," she said. "I thought he would be fabulous for it. I was really trying to get Ben Affleck the part."

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Also? Sarah Michelle Gellar would've been full-on Monet-ing it as Ambuler Amber if it weren't for her "All My Children" responsibilities, and it could've been a pre-"Scrubs" bromantic moment between Donald Faison and Zach Braff, if the latter had been chosen as Josh instead of Rudd. But then again, there were other names in the Murray mix as well, including Dave Chappelle and Terrence Howard.


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