Development
The idea for Clueless first originated as a television pilot in 1993.[8][9][10] 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. 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."[9] 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."[8]
"I remembered reading Emma in college and being struck at how much it reminded me of old TV shows like Gidget. There's something so basic about it. I knew [Clueless] would be set in Beverly Hills because it's a hyper-pastel fantasy place."
—writer and director Amy Heckerling in 2012[9]
As research for the script, Heckerling sat in on classes at Beverly Hills High School to get a feel for the student culture,[11] commenting, "...one thing I observed was these girls in a constant state of grooming."[9] Ken Stovitz had become Heckerling's agent at the time and told her the script had the potential to be a feature film after he read it.[10] The finished script, which was titled "No Worries", contained the main characters that would end up in the Clueless film.[10] Twink Caplan, Heckerling's friend who had worked with her on past projects, said film executives at Fox were wary of the story being too female-oriented to appeal to a large enough audience. "It was obvious they didn't get it. They thought the script needed more boys in it. They were afraid that if they focused on girls, we wouldn't get any guys to see it. So it went into turnaround. It was dead", said Caplan.[9]
Six months later, the script found its way to producer Scott Rudin, who gave it his stamp of approval.[8][9] Rudin's support led to increased interest in the script, and it became the subject of a bidding war between studios which was eventually won by Paramount Pictures.[8] Heckerling was excited, as Paramount owned several major youth-centered TV channels, such as MTV and Nickelodeon, which were suited to the film's target demographic.[8]
Casting
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.[10] When the film was still in development at Fox, executives suggested Alicia Witt, Keri Russell, Gwyneth Paltrow, and Angelina Jolie for the part.[10] Heckerling met with Reese Witherspoon, who already had a few film roles to her credit.[10] Though Silverstone only had the thriller The Crush as her previous film, the studio did not pressure Heckerling to cast big stars, and Silverstone ultimately won the role of Cher.[11] Ben Affleck and Zach Braff auditioned for the role of Josh.[10] Sarah Michelle Gellar was offered the role of Amber Mariens but turned it down due to her commitments to All My Children, while Zooey Deschanel auditioned for the role of Amber as well.[12]
Seth Green auditioned for the role of Travis and Alanna Ubach was considered for the role of Tai.[10] Terrence Howard and Dave Chappelle were considered for the role of Murray.[10] Jeremy Renner and Jamie Walters auditioned for the role of Christian, and Jerry Orbach and Harvey Keitel were considered for the role of Cher's father, Melvin Horowitz.[10][13]
The character of Wendell Hall, played by Wallace Shawn, was inspired by a real-life debate teacher at Beverly Hills High School and a friend of Heckerling's. Prior to full-time acting, Shawn had been a teacher and drew on his experience for his portrayal of Mr. Hall.[11]
Filming
The Westfield Fashion Square in Los Angeles was used for some interior mall scenes.Principal photography for the film began on November 21, 1994,[14] and consisted of a 40-day filming schedule.[15] Brittany Murphy, who was 17 at the time, required a parent or guardian present during filming.[16]
Scenes depicting the fictional Bronson Alcott High School campus including the tennis courts, outdoor cafeteria, and the quad were filmed at Occidental College in Los Angeles.[17] Ulysses S. Grant High School in Valley Glen provided filming locations for the school's interior sets.[18] Other notable filming locations include the former Westside Pavilion shopping mall, Circus Liquor in North Hollywood, where Cher is mugged in her designer dress, and Rodeo Drive, featured in Cher's "crisis" scene as she dejectedly wanders around after a failed driver's test and a confrontation with Tai.[18]
The Mighty Mighty Bosstones performance, originally an outdoor event, had to be moved inside due to rain.[16] Paul Rudd bought everyone gifts after filming wrapped.[19]
Costumes
Mona May did the costume designing for the film. The iconic plaid set worn by Cher Hororwitz in the film was "a nod to a Catholic schoolgirl uniform, but taken to another level and, turned designer."[20] Cher wore several designer clothes ranging from Azzedine Alaïa to Anna Sui.[21] The "underwear" Calvin Klein dress worn by Cher was actually designed by Sui who, at the time, was an emerging designer.[21] Calvin Klein was credited due to more brand recognition during the time.
