The Untold Truth Of Clueless

It's hard to believe it's been more than 20 years since Clueless made its debut in theaters. The quirky coming-of-age teen comedy became an instant cult classic. Today, Clueless is a virtual time portal to all the hipness 1995 had to offer. Watching the film now instantly transports you back to a simpler time, when movies were rented from Blockbuster and phones were used for talking, not texting (because they were all landlines).

Fans of the film have been obsessing over the fashion, the music and the slang for years leaving seemingly no stone unturned. Whether you've viewed it several times or several hundred times, there's a good chance you don't know these untold truths about Clueless.

According to writer/director Amy Heckerling, Clueless is a modern retelling of Jane Austen's Emma. Fascinated with the social mores depicted in the novel, Heckerling pulled Austen's cast of characters and basic plotlines and dropped them into the contemporary setting of Beverly Hills High School, circa 1995. Cher's well-intentioned but misguided attempts at matchmaking closely parallel Emma's journey into young adulthood. Clueless reminds us that learning to navigate the world of gossip, social hierarchy, courtship are timeless rights of passage.

Inspiration didn't come from just one source. Heckerling drew from the comic novel Gentlemen Prefer Blondes by Anita Loos when it came to shaping the characters in Clueless. As she told Jen Chaney, author of As If!: The Oral History of Clueless as told by Amy Heckerling and the Cast and Crew, "I remember reading Emma and Gentlemen Prefer Blondes. Those characters: what I gravitated to was how positive they could be."

While the movie eventually did have a television spin-off, Clueless was originally conceived as a TV show. In the early 90s Amy Heckerling who at the time was best known for directing the movie Fast Times at Ridgemont High began developing on another project that also centered around Southern California teens. Originally called No Worries, the concept soon moved from television to feature film and was eventually re-named Clueless.

Fans of the film have pointed out a continuity flaw concerning Cher's surname. While she answers to Cher Horowitz in class, her report card reads Cher Hamilton. In addition, her father receives a letter addressed to Melvin Hamilton, not Mel Horowitz. So what's with the name change? There is speculation that the goof is a shout out to Heckerling's directorial film debut, Fast Times at Ridgemont High. The classic teen comedy stars Jennifer Jason Leigh as Stacy Hamilton, another strong female lead character created by Heckerling.

Studio bigwigs were worried a step-brother/step-sister romance would be a tad too incestious for audiences to stomach, but Heckerling insisted that's how the lead characters should connect. The step-sibling love story made sense to Heckerling because it happened in real life for her grandparents, who met when they were teenagers.

You can't talk about Clueless without talking about the fashion. The well-planned-out costumes were the brainchild of costume designer Mona May, who counts Clueless as her first feature film. May pulled together looks for each character based on their personalities. For Cher, each outfit was specifically chosen to highlight her character's growth throughout the movie. While Dionne is "wild and sassy and sexier than Cher," May told The Daily Beast, "so we put her in lots of colorful vinyl miniskirts, leopard prints, and quirky hats."

Fashion is certainly one of the main focal points of Clueless. It influences everything from character development to the set design. But not everyone was a fan. Alicia Silverstone confessed that she thought being fitted for so many outfits was annoying and pointless. Silverstone told xoJane that she "had to endure something like 67 outfit changes" as she transforms from self-absorbed teen to a slightly more self-aware young adult. It really was all about the fashion, even down to the backdrop. According to production design, the scenery was purposely kept drab and muted to ensure the clothes popped. But not everyone was a fan of the focus on fashion.

While Silverstone had disdain for her wardrobe, audiences couldn't get enough of Cher's fashion choices, especially that little white mini Cher wears on her first date with Christian. The simple Calvin Klein slip dress prompted the classic father/daughter debate over what constitutes wearing actual clothing (as opposed to parading around in your underwear). The dress was reissued by the design house in 2010.

Who else could pull off self-absorbed-but-sweet so perfectly? It's hard to imagine anyone but Alicia Silverstone as Cher Horowitz. However, there was a bevy of soon-to-be famous actors who auditioned for the part. Future vampire slayer, Sarah Michelle Gellar almost landed the role. And Gellar wasn't the only future A-list actor considered for the lead. Reese Witherspoon, Keri Russell and Tiffani Thiessen and were all in contention to play the fashion-obsessed Beverly Hills teen.

The studio insisted other actresses be considered for the part of Cher. But for Heckerling, the lead was a clear choice thanks to a music video. "I was watching an Aerosmith video of 'Cryin'," explained Heckerling. "That was the first video she was in. And I just fell in love with her."

Travis Birkenstock, the lovable stoner who skates away with Tai's heart was almost played by Seth Green. Instead, the part went to his close friend, Breckin Meyer. In an excerpt from Jen Chaney's book, As If!: The Oral History of Clueless, as Told by Amy Heckerling, the Cast, and the Crew, featured in Vanity Fair, Clueless co-producer Adam Schroeder relayed the story, "You know, it was also funny when Breckin Meyer and Seth Green came in, and it was down to the two of them for Travis. And it turned out they were best friends.... But I'm sure each wanted the part."

We really couldn't imagine anyone else but Stacey Dash in the role of Dionne. Dash portrayed Cher's fashionable partner in crime in the movie and reprised the role in the Clueless television series. But Dionne's white floral crocheted beanie was almost filled by former Fugees member, Lauryn Hill. However, Dash wasn't worried about losing out to the famous singer, and said: "I knew it was my role."

In an even more bizarre alternative casting universe, Dave Chappelle was considered for the part of Murray before Donald Faison nabbed the job. Chapelle impressed Heckerling, but was a bit too jaded to pull off naive high school goofball. "He was just amazing — he was such a mensch," Heckerling explained to The Hollywood Reporter, but "I needed somebody who was really innocent, a goofy kid."

While I'm sure Chapelle would have been excellent in the role, it's hard to imagine him rocking Murray's braces.

The iconic film is a favorite popular culture reference. At the 1996 MTV movie awards, three of the Golden Girls paid homage to Clueless by spoofing the film. More recently, Australian rapper Iggy Azalea gave a nod to the timeless fashion of Clueless by featuring them in her music video Fancy. And rocking the Clueless look is a perennial Halloween costume favorite with adults and even teens born after the film's debut.

It seems like we still can't get enough of Clueless — there's even a musical that's been in the works since 2012. According to Heckerling, Clueless the Musical will use classic songs from the '90s to tell the story.

In 2015, the book As If!: The Oral History of Clueless as told by Amy Heckerling and the Cast and Crew was released in honor of the film's 20th anniversary. Chock full of insider information and original interviews with behind the scenes players, As If! reminds us why Clueless is a timeless cult classic.