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."

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.

"It was the first time I'd seen Angelina Jolie…," Frazier said. "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."