Reese Witherspoon, Angelina Jolie and Gwyneth Paltrow Considered for ‘Clueless’ Lead

By Courtney E. Smith

In a new oral history in the July issue of Vanity Fair, it was revealed that Reese WitherspoonAngelina Jolie and Gwyneth Paltrow were all among the actresses considered for the Cher role, played by Alicia Silverstone, in Clueless.

From the start director/writer Amy Heckerling and casting director Carrie Frazier wanted Silverstone, who they (respectively) spotted in the Aerosmith videos and the film The Crush. But Fox, the studio bankrolling things at the time, only thought she was “okay” after her screen test and asked Heckerling to see more actresses.

“I saw Alicia Witt, the redheaded [actress],” Heckerling recalled. “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.”

If imagining Kelly Kapowski from Saved by the Bell or Felicity as Cher blows your mind, then you will totally get what Frazier thought when she was pitched Jolie for the role.

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