Alicia Silverstone was chosen for Clueless, instead of Angelina Jolie

There was audition for the role of Cher for 1995 movie Clueless and Angelina Jolie was one of them who auditioned for the role.

Jolie submitted an audition tape but according to casting director Frazier, she didn't know what was needed for Clueless. 

Director Heckerling explained why Alicia Silverstone was chosen, “I was watching an Aerosmith video of ‘Cryin’.’ That was the first video she was in. And I just fell in love with her. Then my friend [casting director] Carrie Frazier said, ‘You have to see this girl in The Crush.’ And I was like, ‘No, I want the Aerosmith girl.’ Well, it was the same girl.”