When she first walked onto the screen in July of 1995, it was love at first sight. America was immediately smitten by a ditzy, glitzy Beverly Hills fashion plate named Cher Horowitz. Well, almost everyone. When Alicia Silverstone first read writer-director Amy Heckerling’s script for Clueless in the back of a limo coming home from shooting one of her iconic ’90s Aerosmith videos, she didn’t get Cher. “I thought, ‘Who is this girl?'” says Silverstone. “I had nothing in common with her at all. I thought she was a materialistic, annoying little bitch.” As if!

Over the past 17 years, Silverstone and the rest of the cast (which also includes Paul Rudd, Stacey Dash, Donald Faison, Jeremy Sisto, Breckin Meyer, and the late Brittany Murphy) have not only come to embrace Cher in all of her well-intentioned matchmaking adorableness, they’ve also come to appreciate how a little $15 million high-school comedy changed their lives. In Rudd’s case, that mean teenage guys coming up to him for years, saying, “Dude, you got to make out with Alicia Silverstone!”

Check out video of the cult teen comedy’s class reunion.

In our oral history of the making of Clueless, you’ll learn about some now-famous names who auditioned for the film, but didn’t get cast (Reese Witherspoon as Cher, Terrence Howard as Murray, Lauryn Hill as Dionne), how the male stars spent weeks after the film wrapped sleeping on the floor of Meyer’s seedy apartment watching Corey Haim and Corey Feldman movies, and how they scratched their heads when they first encountered some of the slang that Heckerling’s script made famous (Whatever, Bettys & Barneys, and Monet). “I had no idea what the hell I was saying,” says Faison. “What’s going postal mean? And when they explained to me what it meant, I thought, ‘That’s really messed up!'”

Here’s a sampler of some other Clueless outtakes and tidbits from the story:

*The film was originally pitched as a TV series to Fox TV with the title No Worries. Before being called Clueless, other titles included I Was a Teenage Teenager and Clueless in California. Says Heckerling, “When I grew up there were a lot of movies with titles like I Was a Teenage Werewolf and stuff like that. Clueless in California was just a play on Sleepless in Seattle.”

*While the story was based on Jane Austen’s novel Emma, none of the young crew knew that going in. “I had no idea,” says Silverstone, who was just 17 when the film was made. “I’m so embarrassed. When I was done with the movie they told me about Emma. And I read the book and I was like, Wow, Amy did such a good job. I was reading it and I’d be like, Hey, there’s Justin Walker’s character!”

*Heckerling, who also directed 1982’s Fast Times at Ridgemont High, hung out at Beverly Hills High School as research. What she didn’t know at the time was that both Silverstone and Meyer had gone there, too…as students. “I didn’t live in Beverly Hills,” says Meyer, “but it was a very good public school, so my parents lied about my address and we got me into Beverly Hills High. Alicia went to Beverly, too. I never saw her there, which just proves that I was not a very cool person. I guarantee that she didn’t know I existed.”

*Stacey Dash, who plays Cher’s best friend Dionne, was hardly a teenager at the time. “I was 27, and I was playing this high school student,” says Dash, “and I had a son at home who was six years old.”

*Heckerling intentionally let Silverstone mis-pronounce words because that’s what Cher would have done. “The first day we shot the scene in debate class. And Alicia said, the Hate-i-ans instead of Haitians, and everybody started to run up to her and tell her it was wrong. I had to stop them. It’s much funnier the way she said it. That was Cher.”

*Everybody’s expectations were low. Says Faison, “When we were making the movie, you don’t think the movie’s going to be good. You think, I’m making the next License to Drive. You think this movie’s going to be just for teenagers and that’s it.”

*Silverstone isn’t a very good a hoarder. “I thought the clothes were so wonderful, by the end I wanted all of them. I took a few things here and there. I didn’t do a very good job at saving any of them. I was stupid about that whole thing. I think I gave them all away.” Too bad, she could have made a fortune on eBay.

*Over the years, the film’s cult following has come up with some odd interpretations of the film. “Someone came up to me once and — very serious and teary-eyed — said, ‘I just want you to know that when I saw Clueless and I saw Travis decide to go into a 12-step program, that’s when I decided to get sober.’ There was a part of me that was like, ‘Wow, that’s amazing.’ And there was another part of me that was like, ‘Are you serious? Because I’m pretty sure Travis might have relapsed. But I’m happy you found that.'”

Other reunions in the annual double issue, on stands this week (or available to buy online), include National Lampoon’s Vacation, Arrested Development, Breaking Away, Melrose Place, and E.T. The Extra-Terrestrial.

Entertainment Weekly and some of the stars featured in the Reunions Issue have teamed up with — the global leader in online celebrity auctions — to raise money for a variety of great causes. Fans can bid on memorabilia, meet-and-greets, and more; all proceeds go to charity. Visit and charitybuzz/ewreunion for more information.


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