Silverstone’s performance in an Aerosmith music video helped land her the role of Cher.
It’s hard to imagine anyone other than Silverstone in the role of Cher Horowitz, and it turns out she was one of Heckerling’s top choices from the start.
According to Interview magazine, Heckerling said she had her eye on Silverstone thanks to her role in Aerosmith’s ‘Crazy’ music video.
“Her performance in the video — I believed everything. I was just crazy about her. So when I turned in the script, the ‘Crazy’ video had come out and I was shooting it. I gave it to the studio and said, ‘Think of this girl when she you read,’ and they said, ‘Oh, Liv Tyler?’ And I said, ‘No!'” he said.
He continued, “Meanwhile my friend, the casting director, was like, ‘You’ve got to see the girl in ‘The Crush.’ Well, it’s the same girl.’
The “This is an Alaïa!” The heist scene was based on a true story.
One of the most famous lines in “Clueless” is, “You don’t understand. That’s an Alaïa!”
In the scene, Cher is robbed at gunpoint, but when the robber tells her to get on the ground, she protests because she doesn’t want to ruin her designer outfit.
According to Heckerling, the scene is based on a true story he heard at a dinner party about a man whose wife made him start wearing designer suits.
“He held on and the thief said, ‘Get on the ground!’ He said, “But this is Armani!” It wasn’t like he loved Armani, it was more like he was more afraid of his wife than a guy with a gun,” Heckerling told Interview magazine in 2016. “I thought it was so hilarious!”
Cher’s speech should not have included the mispronunciation of “Haitians”.
Another memorable moment in the film was when Cher mispronounced the word “Haitians” as “Hat-ee-ans” while giving a speech in debate class.
According to Heckerling, the mispronunciation was not always meant to be in the film.
“It wasn’t written that way in the script, but it was [Silverstone] she said,” Heckerling told Vice in 2016. “Everybody started running over to correct her and I had to kind of block them all, like, ‘Get away from the actress!’ I didn’t want him to play. I just wanted him to feel that confidence.”
According to Heckerling, a major network picked up the film, in part because of the romance between Cher and her stepbrother.
The production of “Clueless” was more difficult than fans expected.
According to the same Vice interview, Fox continued to make the film because it wanted to focus more on the male characters, and the network apparently felt that the romance between Cher and her stepbrother was inappropriate.
“It was so stupid,” Heckerling told the publication. “[Fox was] going, “how can you have sex with your stepbrother?!” And it’s like, they’re not related: Their parents were briefly married and [Cher’s] the father is still kind [Josh]. It’s not verbatim, you know?’
After the film was picked up by Paramount, Heckerling said she told producer Scott Rudin about all the things she had taken out of the film to appease Fox, and he allowed her to put it all back into the script.
Heckerling was the inspiration for Tye’s “very harsh” offense.
Another iconic line from the film, “You’re a virgin who can’t drive,” was inspired by Heckerling’s teenage years.
According to Vice, Cher’s virginity and repeated failed driving tests were based on Heckerling’s real life, so it was easy for the director to create the perfect insult from Tai (played by Brittany Murphy).
“You’re a virgin who can’t drive.” Well, that was me! For a long time”. Heckerling explained. “You take what you’re most ashamed of and use it.”
Heckerling also used her own fear of driving as inspiration for Dion’s freeway terror.
In a 2017 interview with The Daily Beast, Heckerling explained that she used her own fear of driving as inspiration for the freeway scene in “Clueless.”
“I’ve always had a fear [driving]. So sometimes in my life I end up in the lane where you can’t get out, and you’re on the freeway for an exit, and I’m pretty much screaming the whole way,” he said. “In Los Angeles it’s like a physical disability. I wanted to make fun of it, how it feels when that happens.”
Some of the wardrobe items in the movie came from thrift stores.
In “As If!: The Oral History of Clueless,” costume designer Mona May said there were 63 outfit changes for Cher, but she only had $200,000 to spend on the entire film’s wardrobe.
I had to go to the store. I had to go to high end shops. I had to make some things and create things because they didn’t even exist in the stores, because they were just thought up and dreamed up by designers at the catwalk shows,” May wrote in the book.
Paul Rudd gave a nod to his alma mater in the film.
Paul Rudd played Cher’s step-brother Josh in the film, and it turns out he made some suggestions to May about his wardrobe.
Rudd is a graduate of the University of Kansas, and according to a 2014 interview with Big Slick Kansas City, he asked the “Clueless” costume team if he could wear his own KU hat for a few scenes.
The actor said he gave his hat to the wardrobe department to keep, but hasn’t seen it since filming ended.
According to Heckerling, the slang from the film came from various people.
The film’s iconic vocabulary — “As if!” “Total Baldwin,” “Whatever!” — has a few different roots.
“I always make up slang words because I’m just interested in how people use language,” Heckerling told The Hollywood Reporter in 2016. For example, she attributed the memorable phrase “As if” to the LGBTQ communities of the early 1990s.
He told Entertainment Weekly in 2012 that he also asked actors auditioning for the film for their ideas.
“That’s when I got to the ‘post office,'” she said, talking about the casting process. “I liked to call someone ‘Monet.’ From a distance they are beautiful and up close they are completely different.”