Could you picture Reese Witherspoon as Clueless' Cher Horowitz?! ... Or how about Gwyneth Paltrow, or even Angelina Jolie?
In a new Vanity Fair interview with director Amy Heckerling to celebrate the now-classic film's 20th anniversary, she reveals that a number of A-listers were very much interested in the role that eventually went to Alicia Silverstone.
"I had my heart set on Alicia," Heckerling explains. "[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."
Casting director for Fox at the time, Carrie Frazier, also remembers seeing Angelina Jolie.
"But she was too knowing for what was needed for Clueless," she recalls. "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.'"
But it's Reese Witherspoon, who actually met with Heckerling at the bar of the Four Seasons hotel in Los Angeles for the role, who came the closest to nabbing the part.
"I met with Reese [Witherspoon] because everyone said, 'This girl is amazing. She's going to be huge,'" she remembers. "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."
And although Paul Rudd was adorable as Cher's stepbrother/love interest, Josh, Frazier says she was actually "heartbroken" that the role didn't go to Ben Affleck.
"I brought in Ben Affleck, for the role of Josh. I thought he would be fabulous for it," she reveals. "I was really trying to get Ben Affleck the part."
"Ben Affleck told me [later that] he read," Heckerling adds. "But I don’t remember that."
Another future superstar surprisingly considered for a role in the beloved 1995 film was comedian Dave Chappelle. But the part of Murray -- Cher's best friend Dionne's boyfriend -- eventually went to Donald Faison.
"I do remember that I saw Mel Brooks' movie [Robin Hood: Men in Tights]. And I loved Dave Chappelle. I met with him in New York," Heckerling recalls. "Donald had a much more kid-like energy. And Dave [had] a very cynical, grown-up, funny, comic kind of thing that I felt was maybe a little too edgy."
Interestingly enough, Faison's BFF and Scrubs co-star Zach Braff is said to have also auditioned for the role of Josh, and Empire's Terrence Howard was another "top contender" for Murray. The part of Cher's nemesis Amber (Elisa Donovan) was also first offered to Sarah Michelle Gellar, who had to pass thanks to her role on All My Children at the time.
But one actress the Clueless director says was a shoe-in from the beginning was the late Brittany Murphy, who stole the show as the adorably innocent Tai.
"When I met Brittany, I was like: 'I love her. I want to take care of her,'" she remembers. "She was just so bouncy and giggly and just so young. I mean, when you saw her, you just smiled."
In July 2013, Faison and Stacey Dash (Dionne) actually staged a mini Clueless reunion during an episode of TV Land's The Exes. Watch the adorable scene below!