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Arts and Entertainment

Behind-The-Scenes Stories You Didn't Know About 'Clueless'

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It's been 20 years since Clueless debuted, and we still feel nostalgic every time we see Cher's game-changing yellow plaid ensemble or hear the catchphrase "as if!"

The seminal '90s film updated the teen comedy, a genre that hadn't gotten much play since the '80s. Movies like She's All That and Can't Hardly Wait would follow in Clueless' wake. "Teen movies were just not happening. It was almost like a relic of the John Hughes movies in the 80s," Clueless co-producer Adam Schroeder said in Jen Chaney's recently-released book, As If!: The Oral History of Clueless, as Told by Amy Heckerling, the Cast, and the Crew.

People have also often compared Mean Girls to Clueless. "When I think about Mean Girls I feel like Mean Girls is a hybrid—and I'm sure someone has said this before—a hybrid of Clueless and Heathers," Chaney told Harper's Bazaar. "It has that sort of dark streak in it. Clueless, even though there's elements of satire in it, I don't think it's really a mean-spirited movie at all. Mean Girls is a little bit more actively cynical than Clueless is, which is where the Heathers element comes in."

When Clueless first hit the box office on July 19, 1995, it was a sleeper hit that ranked number two its opening weekend, right after Apollo 13. It would eventually make $56 million domestically—not bad for a film that cost about $12 to $13 million to make.

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It developed a fervent cult over time that has only grown as millennial nostalgia for the 90s has been cresting (which is baffling The Olds). Last year, Iggy Azalea paid homage to the film with her "Fancy" music video, even donning Cher's (Alicia Silverstone) yellow-and-black plaid number and recreating the Dionne (Stacey Dash) and Murray (Donald Faison) freak-out on the freeway scene.

Chaney revealed a lot more in her book, including details about the casting, where she got the inspiration for the story and the fashion. Here are some of the facts about the movie that we found most interesting.

The Plot:

We all know that Clueless, a story of a privileged Beverly Hills teen with a penchant for matchmaking, is loosely based on Jane Austen's novel Emma. However, it turns out Cher and Josh's (Paul Rudd) stepsister and ex-stepbrother romantic relationship was based on Clueless writer-director Amy Heckerling's family story. Heckerling's grandparents were stepbrother and stepsister, and got married to each other.

"Totally not blood-related," Heckerling says in Chaney's book. "When I was a kid all she did was complain about her stepmother to me ... but her step brother, whom she later married, was always a protector. They were married. They knew each other from the time they were teenagers. They were so dependent on each other and so angry all the time with each other. Anyhow, that cracked me up. So it did not seem like a crazy thing to me [for Josh and Cher to be together]."

The Cast:

It's hard to imagine anyone else playing Cher, Josh, Murray, and basically all of the characters in Clueless. They're a bunch of Baldwins and Bettys! Carrie Frazier, the casting director for the film, once considered Reese Witherspoon for the role of Cher. Gwyneth Paltrow was considered as well, but she pooh-poohed the film while promoting the movie Emma, which came out the following year. She told New York Magazine (while taking a drag off a Camel): "I think it’s sad that America’s first cultural reference to this movie will be Clueless. I mean, honestly."

Ben Affleck was a top contender for Josh, though Zach Braff also read for the part *shudder*. Sarah Michelle Gellar was offered the part of Amber, which would later be portrayed by Elisa Donovan. However, that fell through when the head honchos behind the show Gellar was working on, All My Children, wouldn't let her leave for two weeks to film Clueless. Terrance Howard and Dave Chapelle were even both considered for the role Faison would later snatch.

The story that's wiggin' us out the most is that Rudd also read for the role of Murray. "When I auditioned for it, I had also asked to read for other parts [including Christian and Murray]," Rudd said in Chaney's book. "I thought Murray was kind of a white guy wanting to be black. 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."

The Fashion:

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Clueless' fashion was best known for its babydoll dresses, A-line skirts paired with knee-high socks, and high-end hats. And of course, that matching yellow and black plaid blazer and skirt Cher wore. Mona May, Clueless' costume designer, who also worked on Romy and Michelle's High School Reunion and Enchanted, had a small budget for clothing, but ended up dropping big bucks for Cher's yellow plaid outfit. It was actually an original Dolce & Gabbana.

"It was about taking fashion from all different sources and predict what would be on the street six months ahead, like a fashion designer would," May told Vanity Fair. "Amy and I both love plaid, and I think there is nothing better to have than a quintessential plaid skirt for a girl’s first day of school. But we had to go further with that [idea] for the movie, so we had to have the complete suit."

When the movie came out, grunge was the "it" fashion best embodied by a pre-makeover Tai (Brittany Murphy) who wore flannel and baggy clothes. "I think what you said earlier about this coming out of the grunge movement, I think that's right," Chaney told Harper's Bazaar. "I think that was Mona's intention and Amy Heckerling's intention—to sort of do something that was to be a departure from that and to sort of give girls permission to be girly again."

As for the hats: "I always get hats, but never have the nerve to wear them,” Heckerling told Vanity Fair. "Hats are a thing that are really stylish, but you have to have the confidence to pull it off. And Cher and Dionne do. At the time there was that rave culture, where for a brief moment in time people were being more creative with their clothing. And you would see a lot of crazy hats at raves—like a top hat or Dr. Seuss hat, and Mona found a way to make them stylish."

The Origins:

Clueless was originally developed as a TV show for Fox about popular kids at a California high school, with the central character being an overly optimistic girl. Lots of different titles were thrown around for that show, including No Worries and I Was a Teenage Teenager before Fox movies saw potential in the show to be a feature film. However, it was Paramount that took the film under its wing in the end. Eventually, it did become a UPN TV show that didn't live up to the film's greatness.

The Soundtrack

There are moments in Clueless that are forever etched into our minds as being paired with music. When Tai finally gets some one-on-one time with Elton (Jeremy Sisto) at a house party in the Valley, she rolls her hands to Coolio's "Rollin' with the Homies." Or when Supergrass' "Alright" bubbled in the background of Cher's photo shoot by the fountain. And we'll definitely never forget when the Mighty Mighty Bosstones performed live at the party where Josh saves the night by dancing like a dweeb with Tai.

Heckerling and music supervisor Karyn Rachtman, who also worked on the soundtracks for Pulp Fiction and Boogie Nights, mixed together a blend of upbeat alt-rock, ska, pop and rap from some up-and-coming artists and some established ones, like Counting Crows, Jill Sobule, Radiohead and Luscious Jackson. There was even a cover of the 1981 track "Kids in America" performed by the Muffs, and David Bowie's "Fashion" in the mix.

"Amy [Heckerling] really is a music fan, but all the music she wanted to use was ’80s! And '70s and '60s too," Rachtman told Flavorwire. "The film had this timeless feel, even though it’s so ’90s."

Cher calls Radiohead "complaint rock," something Rachtman felt the same way at the time. "I looked at them as ‘the whiny band,’ and I was very, ‘Whatever’ on them," she told Flavorwire. "I became a Radiohead fan later on, but I remember hearing at the time that they were assholes. I had to go to England to show them Clueless, and Thom Yorke was such a great guy. I may have really played up how shallow Cher was, like, 'Of course she’s going to call you whiny, it’s a compliment, get it?' They were fine with it."

The soundtrack went platinum by 1998. In celebration of its 20th anniversary, the soundtrack was re-released in April. Urban Outfitters is even selling a special reissue that's on yellow and black plaid vinyl.