Secrets Behind ‘Clueless’ Amid the Film’s 30th Anniversary, Including the Classic Book That Inspired It

The 1995 film Clueless has turned 30 – and everyone is totally buggin’ that the coming-of-age comedy has come of age!

Writer-director Amy Heckerling’s modern-day take on Jane Austen’s classic 1815 novel Emma stars Alicia Silverstone as Cher Horowitz, who navigates her way through teenage angst as the popular girl at Bronson Alcot High in Beverly Hills.

The film features a who’s who of up-and-coming Hollywood hotshots, including Paul Rudd (Josh), Stacey Dash (Dionne), Brittany Murphy (Tai), Jeremy Sisto (Elton), Breckin Meyer (Travis) and Donald Faison (Murray), supported by veteran actors Dan Hedaya (Cher’s dad, Mel Horowitz), Wallace Shawn (Mr. Wendell Hall), Twink Caplan (Miss Toby Geist) and Julie Brown (Coach Millie Stoeger).

Heckerling recalls reading Emma in college, saying to Entertainment Weekly, “There’s something so basic about it. I knew [the movie] would be set in Beverly Hills because it’s a hyper-pastel fantasy place. I hung out at Beverly Hills High School for research. And the one thing I observed was these girls in a constant state of grooming.”

Still, she had to fight for the film. “After a couple of [teen-targeted] movies like PCU and Airheads came out and didn’t do so well, Fox got scared,” Heckerling reveals. “Everybody in town pretty much passed on it.”

Luckily, producer Scott Rudin “got it” and had a deal with Paramount — and Heckerling knew exactly who she wanted to play Cher … Silverstone, who had caught her eye in Aerosmith music videos and didn’t even have to audition for the part.

“I loved her from [the videos], and when I met her I had these feelings, like, I just want to watch her,” the director recalls to Vogue. “I want to take care of her. I think men and women will like her. She’s so pretty, she’s so sensual, and she’s also somebody that you seem to care for.”

Silverstone’s “clueless” pronunciation of the word “Haitians” as “Hate-ee-ans” in one memorable debate class scene was a happy accident that the director kept in the movie.

“It wasn’t written that way in the script,” Heckerling reveals in an interview with Vice, “but that’s how she said it. Everybody started to run toward her to correct her, and I had to kind of block them all, like, ‘Step away from the actress!’ I didn’t want her to act, I just wanted her feel that confidence.”

Clueless is filled with now iconic slang. Heckerling says “hymenally challenged” was her own answer to growing PC terminology of the ’90s; “as if” came from a friend; a crew member suggested the phrase “going postal”; and “keeping it real” naturally sprang from actor Donald Faison on set.

What about “whatever”? Confides Heckerling, “I read in a linguistics study that it was the least favorite word of the year. It just works in so many situations.”

While E! News reported Heckerling named the two leads Cher and Dionne “after famous singers of the past who now do infomercials,” Cher has two last names, by accident!

Cher’s report card lists her name as “Hamilton,” but she got a different moniker in a classroom scene. “I never really had anybody in the script say her last name,” Heckerling explains to Vogue. “And then the prop guys must have said, ‘Give us a last name.’ In one scene, Wallace [Shawn] was taking attendance, and he sort of ad-libbed Horowitz. He just ad-libbed a last name. It’s not used anyplace else. In my script, she’s Cher.”

The scene where Dionne freaks out behind the wheel? That was sparked by Heckerling’s own fear of driving. “Any time I wind up in the lane where you can’t quickly turn off of it and it’s turning into the freeway, I just start screaming until I’m off of it,” she says to Vogue.

Another memorable scene has the characters playing “Suck and Blow,” a game in which a credit card is passed between people using only their lips. The cast found it nearly possible, so a prop card made out of cardboard was created. That didn’t work either. Even holes were drilled into the card, but still no dice. Finally, they made it work by having the actors apply a generous slather of ChapStick to their lips.

In the end, Clueless turned out to be a surprise hit, raking in a whopping $88 million at the box office. Its budget? A mere $12 million!