Gwyneth & Angelina Were Almost In Clueless? As If!

One hot summer day in July 1995, the kids in America looked out their dirty old windows and ran headlong into a cultural phenomenon called Clueless. It's been 20 years since we first met Cher, Dionne, Tai, and Josh. Twenty! It's hard to imagine anyone besides Alicia Silverstone, Stacey Dash, Brittany Murphy, and Paul Rudd playing those now-iconic characters. Who else could deliver the line, "You're a virgin who can't drive?" Vanity Fair just published an excerpt from the new book As If! The Oral History of Clueless, as Told by Amy Heckerling, the Cast, and the Crew, which offers up some surprising candidates. Heckerling, the film's writer and director, says that she had her heart set on Alicia Silverstone as Cher from the very beginning, but the studio wanted her to explore other options. She recounts that she saw Alicia Witt, Tiffani Thiessen, and Keri Russell. "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," Heckerling reminisces. Someone also pitched Angelina Jolie for a role in the film, but Carrie Frazier, who was the film's casting director at Fox, knew she wasn't right. "It was the first time I’d seen Angelina Jolie… 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.'" Frazier was later able to cast Jolie in Gia. Frazier also had Heckerling meet with Reese Witherspoon, because everyone was predicting that her career was going to blow up. "I did see some scenes of [Reese's] and went: Wow. She’s amazing. But Alicia is Cher," Heckerling says. Frazier recalls bringing in Ben Affleck to read for the role of Josh, but that's when her involvement with the film ended, because it changed studios (from Fox to Paramount). Apparently, that's when Affleck's involvement ended as well. Josh, it seems, was the most difficult role to cast. Since he was older than Cher, and their relationship had that step-sibling element (which could be interpreted as incestuous, although the characters aren't technically related), he had to be perfect. Even though they liked Paul Rudd and had him come back to read several times, they ended up letting him go. He took a part in another film, cut his hair, and then the team at Clueless called him back and acted all upset that he'd cut his hair for the job he had gotten. Oh, Hollywood! As far as other characters, Dave Chappelle and Terrence Howard were both strong contenders for the role of Murray. The team wanted Sarah Michelle Gellar to play Amber, but she couldn't get out of her contract over at All My Children. Once all the roles had been cast, everyone gathered for their first table read. Afterward, the cast went out for drinks. "How cool would it be if this thing had legs?" Paul Rudd remembers wondering. He was kind of psychic, but that's another movie quote for a different oral history. (Vanity Fair)