The new book "As If!: The Oral History of Clueless as told by Amy Heckerling and the Cast and Crew," is busting at the spine with juicy tidbits that helped shape the 90s teen classic.

In a new excerpt featured in the July issue of Vanity Fair, author Jen Chaney uncovers some of the film's early casting could-have-beens, including Reese Witherspoon as Cher and Ben Affleck as her ex-stepbrother/lovah, Josh.

"I met with Reese [Witherspoon] because everyone said, 'This girl’s amazing. She’s going to be huge,' reveals Clueless writer/director Amy Heckerling. "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."

"I had my heart set on Alicia [Silverstone]," she admits. "[But] Fox… wanted me to explore all the [options]. 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. 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."

Angelina Jolie was called in to read for the part was deemed too "knowing" by casting director Carrie Frazier.

As for Josh, Cher's socially conscious ex-stepbrother famously portrayed by Paul Rudd, that almost wound up being a relatively unknown Ben Affleck.

"I brought in Ben Affleck, for the role of Josh," reveals Frazier. "I thought he would be fabulous for it. I was really trying to get Ben Affleck the part."

Rudd reveals that he had originally read for Christian and Murray. "I thought Murray was kind of a white guy wanting to be black," Rudd confesses. "I didn’t realize he was actually black. Also I thought: I haven’t seen that character before, the white guy who’s trying to co-opt black culture. But, well: that character is actually going to be African-American. Oh, O.K."

Other actor's considered for the role of Murray: Terrence Howard and Dave Chappelle.

As for Amber: "I really loved Sarah Michelle Gellar, who was on All My Children at the time," says producer Adam Schroeder. "She played Erica Kane’s daughter, and she was just kind of wicked, beautiful. I showed Amy tapes of her. We ended up offering her the part of Amber. There became a big negotiation for All My Children to let her out. It was just for a couple of weeks, and they absolutely stuck their feet in [and] wouldn’t let her."

Get even more Clueless tea by picking up a copy of "As If!: The Oral History of Clueless as told by Amy Heckerling and the Cast and Crew" when it comes out on July 7.