Top 10 Behind-the-Scenes Facts about Clueless

It’s no secret that a big part of what makes “Clueless” such an iconic movie is the amazing fashion we see throughout the film. With a plethora of incredible outfits and a wide array of different plaids, it was a treat for fashion lovers everywhere. There’s no teenage girl who didn’t dream of having Cher’s closet. Except maybe Alicia Silverstone. The actress described having more than 60 outfits! While that might sound like a dream to many, she found the fittings irritating. At first, she had a hard time grasping why clothes were so important to Cher - but admitted to wanting to take all of the outfits home by the end!

Jane Austen’s Emma provided a loose framework for writer-director Amy Heckerling when she was creating the world and characters of Clueless. The novel tells the story of Emma Woodhouse, who much like Cher is a confident girl living a pampered life that shields her from life’s harsh realities. As such, the titular character often involves herself in other peoples’ business. Does that sound familiar? Heckerling has previously said that in reading Emma, she realized how the bones of its plot could be applied to film and television. While Clueless and Emma might not initially seem like they have much in common, there are a lot of similarities beneath the surface in terms of themes and character development!

Everyone remembers the cruel moment where Tai insults Cher’s lack of experience. Well, it turns out that Amy Heckerling drew from personal experience there. Speaking to Interview magazine, she explained, “I was the last American virgin. I didn’t know anybody who didn’t have a boyfriend when I still didn’t and I failed the driver’s test five times.” Funnily enough, the late Brittany Murphy once revealed that she was just as inexperienced when she delivered the line! And that’s not the only part of her own life that Heckerling incorporated. The scene where everybody loses their mind as Dionne accidentally gets on the freeway came from how much she dreads doing so herself! Instead of letting past insecurities get her down, the writer-director turned them into comedy gold.

It’s hard to hear Coolio’s “Rollin’ With My Homies'' and not instantly picture the move Elton teaches Tai as they sing along to the tune. It’s a relatively quick moment in the film, but it left a lasting impression on the audience. The actor behind Elton, Jeremy Sisto, has said that people often bring it up when they meet him. Yet he explained that it actually wasn’t a choreographed move! That’s right, he winged it. He said, “I did my go-to, funny, whatever-I-thought-was-a-douche-y dance at the time. I remember being kind of uncomfortable about it because I was awkward about dancing.” Well, he made it look perfectly natural!

Everybody knows Paul Rudd as the lovable guy that doesn’t age, who brilliantly brought Josh to life in “Clueless”. But what some fans might not know is that he attended the University of Kansas. And he holds his alma mater close to his heart. In fact, the KU Josh is seen sporting throughout the movie belonged to Rudd himself. They incorporated into his character’s wardrobe at his request. Naturally, he gave it to the costume department for safe keeping. Yet funnily enough, he has no idea where it ended up. That’s right, Rudd hasn’t seen his beloved hat since the movie wrapped! He definitely made his school proud though.

Getting Clueless made was a complicated process. Amy Heckerling’s original idea was actually for a Fox TV show called “No Worries”! It was then decided that it should be a movie, and 20th Century Fox purchased it. But the path forward was still far from simple. Heckerling explained that the executives wanted her to make a lot of changes. Namely, they didn’t think a film centered around a teenage girl would work, and didn’t want Cher and Josh to be (ex) step-siblings. What followed was a period plagued by rejection. Eventually, Scott Rudin signed on as a producer, the film found a home at Paramount, and Amy got to tell the story her way. Plus, the movie’s astronomical success actually spawned a TV show by the same name!

Clueless’ casting process was extensive, to say the least. While Heckerling wanted Alicia Silverstone to play Cher as soon as she saw her in an Aerosmith music video, plenty of actresses were in the running. And the woman behind everyone’s favourite lawyer, Reese Witherspoon, was a front-runner. Other stars who were considered for various roles include Tiffani Thiessen for Cher, Ben Affleck for Josh, Terrence Howard and Dave Chappelle for Murray, and Lauryn Hill for Dionne. Even Jeremy Renner read for Travis! As for the part of Amber? It was offered to Sarah Michelle Gellar, but she had to turn it down because of her job on “All My Children”. Honestly, it’s hard to imagine the cast being any different than it was.

One of the best scenes in Clueless is undoubtedly Cher’s speech in debate class. Part of what makes it so great is the way she says “Haitians”. The mispronunciation, coupled with how confident Cher is, makes for an unforgettable combination. Well, it turns out that hilarious moment wasn’t planned: Alicia Silverstone really thought that was how it was pronounced. Amy Heckerling realized that while technically incorrect, the way she said it was perfect for the character. So, she didn’t let anyone correct her. She told Vogue, “I didn’t want her to know that she had it wrong, I wanted that assurance without her thinking this is funny or a joke—which changes how you say things”. We’re certainly grateful Heckerling recognized the magic in the mistake!

One of the greatest things about Clueless is the teens’ use of slang. So how did Amy Heckerling come up with the group’s unique way of speaking? It actually stemmed from her life-long fascination with language, and the ways different groups utilize it. She made some expressions up herself, and used a slang dictionary to find terms like “Baldwin” and “Monet”. Plus, she credits the LGBTQ community for the now iconic “as if”, and incorporated Yiddish vernacular throughout as well. Of course, she also drew on suggestions from the cast and crew. That’s how “postal” and “keepin’ it real” made it into the film! From Bettys and Barneys to totally buggin’, it’s easy to see why fans quote Cher and her friends to this day.

Who could ever forget the yellow plaid ensemble Cher dons? 25 years later, it’s still used as fashion inspiration. So fans might be surprised to hear the Dolce & Gabbana set was almost a different colour! Speaking to Vogue, Alicia Silverstone explained that there were also blue and red versions of the look. So why the yellow one? In an interview, costume designer Mona May elaborated on the choice. She said “We tried a blue suit, which was just great with the blond hair. We tried a red suit, which was a little bit trying too hard. And when she put the yellow one on, it was like, ‘Yes!’ That yellow was like a ray of sunshine, like she was the queen.” The rest, as they say, is history.