The idea for the 1995 film “Clueless” first originated as a television pilot in 1993. Writer and director Amy Heckerling said: “Twentieth Century Fox said they wanted a show about teenagers—but not the nerds. They wanted it to be about the cool kids. The most successful character in anything I’d ever done was Jeff Spicoli in ‘Fast Times (at Ridgemont High’ (1982). People think that’s because he was stoned and a surfer. But that’s not it. It’s because he’s positive. So I thought, ‘I’m going to write a character who’s positive and happy.’ And that was Cher.” Heckerling, having read the Jane Austen novel “Emma” in college and loving the title character’s positivity, decided to write the script around an Emma-like character, saying, “I started to think, ‘What’s the larger context for that kind of a ‘nothing can go wrong’ ‘always looks through rose colored glasses’ kind of girl? So I tried to take all the things that were in this sort of pretty 1800s world and see what would that be like if it was in Beverly Hills.”
Heckerling first saw Alicia Silverstone in the Aerosmith music video for “Cryin'” and kept her in the back of her mind for the role of Cher. When the film was still in development at Fox, executives suggested Alicia Witt, Keri Russell, Gwyneth Paltrow, and Angelina Jolie for the part. Heckerling met with Reese Witherspoon, who already had a few film roles to her credit. Though Silverstone only had the thriller “The Crush” (1993) as her previous film, the studio did not pressure Heckerling to cast big stars, and Silverstone ultimately won the role of Cher.
According to “As If!” a book by Jen Chaney celebrating the twentieth anniversary of this film, though many people think the costuming budget must have been high for the film, it was actually quite modest for a big blockbuster film. Costume designer Mona May wanted the girls to look like mall rats, not models, so her 63 outfit changes only cost $200,000. The biggest costume expense was the plaid Jean Paul Gaultier outfit Silverstone wears in the opening scenes, an outfit that she got to keep, along with all her outfits from the film which, as she told Entertainment Weekly magazine, she gave away to charity.
Silverstone actually did not know how to correctly pronounce “Haitians” in the classroom scene. Heckerling told the crew not to correct her because she liked it so much and wanted it to be in the film.
