Alicia Silverstone Beat Out Reese Witherspoon, Gwyneth Paltrow for Clueless Role

Reese Witherspoon and Gwyneth Paltrow
Alicia Silverstone beat out both Reese Witherspoon and Gwyneth Paltrow for the role of Cher in 1995's Clueless. Paul Zimmerman/WireImage.com

As if? Alicia Silverstone portrayed spoiled Beverly Hills rich girl Cher Horowitz perfectly in 1995’s Clueless, and in a new interview, the film’s writer-director Amy Heckerling reveals that the movie’s leading lady role was highly coveted by Hollywood’s A-list.

“I had my heart set on Alicia. [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,” Heckerling recalls in As If!: The Oral History of Clueless, which was excerpted by Vanity Fair. 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.”

When Paltrow missed out on her chance to read for Heckerling, Reese Witherspoon was waiting in the wings. “I met with Reese because everyone said, ‘This girl’s amazing. She’s going to be huge.’ 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,” Heckerling said. (Not to be outdone, Witherspoon went on to star in equally acclaimed flicks including Cruel Intentions and Legally Blonde after the release of Clueless.)

clueless cast
The cast of Clueless: Justin Walker, Elisa Donovan, Stacey Dash, Alicia Silverstone, Jeremy Sisto, Brittany Murphy, Donald Faison, Breckin Meyer, and Paul Rudd Paramount/Courtesy Everett Collection

Angelina Jolie‘s name was bandied about by Heckerling’s colleague Carrie Frazier on the casting team, who writes in As If that she watched Jolie’s audition tape but did not ask the actress to read in person because Brad Pitt‘s wife was “too knowing for what was needed for Clueless.”

Once she had her fill of second string contenders, Heckerling zeroed in on Silverstone, now 38. The role of Silverstone’s that drew Heckerling in: Her appearance in Aerosmith’s 1993 music video for “Cryin.'” Silverstone was also in Aerosmith’s “Crazy” and “Amazing” videos.

Cast alongside the likes of Brittany Murphy (Tai), Jeremy Sisto (Elton), and Elisa Donovan (Amber), Silverstone knew the role would catapult her career to a new level. “I remember when I read the script the first time, thinking, ‘Oh, she’s so materialistic’ — that I was judging [Cher] instead of being delighted by her,” Silverstone said in As If!. “I remember thinking, ‘This is so funny and I’m not funny.’ But once I was playing her, I just had so much fun being her. I loved how seriously she took everything. She was so sincere and so serious. And that’s what I think makes her so ridiculous and lovely all the time.”

Clueless’ Cher wasn’t the only character that major players fought over in the casting phase. As described in Vanity Fair, Ben Affleck and Zach Braff were high on the list to play Josh, as were Terrence Howard and Dave Chappelle for Murray. Another surprise: Sarah Michelle Gellar was a front-runner for the role of Amber.

Stacey Dash, on the other hand, was a lock for Heckerling’s Dionne character. “In my brain, Dionne was like royalty. I wanted someone that felt like they were part of a royal family in some country somewhere,” the exec remembered. “[Stacey] had that. She didn’t have to act like ‘I’m a snotty bitch’ — she just had that feeling of power and grace, as though she was ready to wave to the public.”

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