This week, everyone is celebrating the 20th anniversary of one of the most classic films of all time, Clueless. I haven’t seen it in years but I could probably sit here and recite the entire script from memory. It was an absolutely genius move for writer/director Amy Heckerling to adapt Jane Austen’s Emma in a modern Beverly Hills setting. It’s absolutely perfect. So to celebrate the anniversary, everyone involved with the process of making it has been spilling some interesting details. Like… an agent pitched Angelina Jolie for Cher Horowitz. OMG. So that’s why I’m including all of these photos of Angelina in Hackers, which was released around the same time: this is what Angelina looked like circa 1994-95

“Clueless” was one of the defining movies of the ’90s — and now, 20 years later, Vanity Fair has revealed some major casting secrets! While director Amy Heckerling says she “had her heart set on Alicia Silverstone” from the beginning, she explains that Fox wanted her to explore other options for Cher.

“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,” she tells the mag. “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.”

Even Angelina Jolie was initially considered for the lead role!

“She was too knowing for what was needed for Clueless,” Fox casting director Carrie Frazier reveals. “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.”

Reese Witherspoon also was in the running for the part.

“I met with Reese because everyone said, ‘This girl’s amazing. She’s going to be huge,’” Heckerling adds. “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.”

[From TooFab]

I could totally see Reese Witherspoon as Cher. That would have been a good backup casting choice for Alicia Silverstone. Gwyneth was good as the OG Emma in the straight-up film adaptation of the book a few years later, but I’m glad Goop didn’t get her hands on Cher. As for Angelina… yeah, no way in hell she would have ever been cast as Cher. But it’s funny that someone, somewhere was like, “Send Angelina’s tape to Amy Heckerling!”

Photos courtesy of ‘Hackers’ and ‘Clueless’.