20 facts you might not know about 'Clueless'

Clueless is awash in '90s culture and lingo and steeped in the Beverly Hills aura. Naturally, it’s an adaptation of an 1815 British novel. No, really. Clueless is, admittedly loosely, based on Jane Austen’s classic Emma, which has gotten more-traditional adaptations starring Gwyneth Paltrow and Anna Taylor-Joy over the years.

Amy Heckerling, who wrote and directed Clueless, was asked by 20th Century Fox to bring them a TV show. Originally, Clueless was going to be a TV pilot in the 1993 season, but at the time, it wasn’t really Clueless. Heckerling told The Telegraph in 2015 that the studio approached her because they wanted a show about teenagers, specifically “cool kids” and not “nerds.”

It’s easy to see why the studio wanted Heckerling on the project. She had made her name directing another iconic teen story, Fast Times at Ridgemont High. Heckerling reckoned that Jeff Spicoli was the most popular character in anything she had worked on, and in her mind, Spicoli was so well-liked because he was positive. This gave her the idea to create a character that was positive and happy, and that was Cher Horowitz.

While working on the screenplay, Heckerling went to Beverly Hills High School to observe the students and add authenticity to her script. One thing she noticed? She told Entertainment Weekly that the girls in the school were in a “constant state of grooming.”

Eventually, Heckerling’s project went from a pilot to an entire film, initially titled No Worries. Executives at Fox weren’t happy with it, though. According to Heckerling’s friend and collaborator, Twink Caplan (who plays Ms. Geist in the movie), they thought the story was too female-focused for a wide audience. Clueless went into turnaround at Fox, leaving it effectively dead as a project. Then, producer Scott Rudin found the script and got behind it. After a bidding war, the movie ended up at Paramount.

When Fox was developing the project, they bandied about actresses like Angelina Jolie, Keri Russell, and Alicia Witt for the lead role of Cher. Heckerling also met with Reese Witherspoon for the part. In the end, none of them would get the role.

Before being cast as Cher, Alicia Silverstone was best known as “that girl from that one Aerosmith video.” She only had one film, The Crush, to her name. However, Heckerling had seen the video for “Cryin’” and liked Silverstone for Cher. The studio put no pressure on Heckerling to cast a known name, so Silverstone won the part.

A young Paul Rudd ended up playing Josh, leading to a good two decades of people comparing photos of Rudd now to Rudd then as proof that he simply does not age. We could have missed out on that opportunity. Ben Affleck and Zach Braff auditioned to play Josh, too.

Imagine a version of Clueless where Harvey Keitel plays Mel Horowitz. Apparently, he was considered, which would have made for a very different film. Jerry Orbach was also in consideration, but Dan Hedaya ultimately ended up winning the role.

Terrence Howard and Dave Chappelle were reportedly in the mix to play Murray, a role that went to Donald Faison. Seth Green was considered for Travis, Breckin Meyer’s role, which is very fitting for the era. Alanna Ubach was up to play Tai, but Brittany Murphy got the part. Notably, since Murphy was still only 17, she had to have a guardian on set.

Wallace Shawn’s character Mr. Hall was inspired by a real debate teacher at Beverly Hills High School. However, Shawn had some inspiration of his own. Before his acting career took off, Shawn had worked as a teacher. He was able to tap into his personal experiences.

Cher and her friends live in Los Angeles, and the movie was shot there. Real locations, like Circus Liquor and Rodeo Drive, played themselves, so to speak. The exterior of Bronson Alcott High is actually Occidental College, while Ulysses S. Grant High School in Valley Glen provided the interiors.

It’s not uncommon for a teenager to be played by an older actor. By and large, the actors in Clueless are around the age they are playing. As we noted, Murphy was only 17 when filming began. Even Rudd, who plays a college student, was 25. Dash was a bit older than her character Dionne, though. She was 29 at the time.

The analog to Christian in Emma is Frank Churchill. Emma and Frank can’t be together in the book because Frank is secretly already engaged. With a high school story, that doesn’t work as a believable complication. Christian was turned into a gay character to keep him and Cher apart.

When filming in Los Angeles, it’s understandable if you don’t prepare for rain. During the filming of Clueless, though, the weather ended up changing things. The Mighty Mighty Bosstones’ performance in the film was supposed to be outdoors, but then L.A. was hit with rain that day. This meant having to move things indoors.

Rudd had done some TV work before 1995, but his first two films came out that year. (He was also in Halloween 6: The Curse of Michael Myers). The opportunity seemed to be appreciated by the young actor. He bought gifts for his fellow cast members after filming wrapped, according to Jen Chaney's 2015 book As If!: The Oral History of Clueless as Told by Amy Heckerling, the Cast, and the Crew.

The executives at Fox that passed on Clueless were worried about nothing. The film debuted second at the box office, and it would end up making $56.6 million off of a $12 million budget. It was also a critical hit. The movie has an 81 percent rating on Rotten Tomatoes, and Roger Ebert gave it three-and-a-half stars.

Heckerling helped break Silverstone as a star, and they would work together many years later. In 2012, Heckerling wrote and directed the vampire comedy Vamps. It starred Silverstone and also had Shawn show up in a role.

Clearly, this movie struck a chord with people. It spawned a series of books in the ‘90s aimed at teenage readers. A comic book series debuted in 2017. There was a computer game released in 2009. Perhaps most notably, there was a musical, written in part by Heckerling, that debuted off-Broadway in New York. Alas, it wasn’t meant to be. The show opened on Dec. 11, 2018, and closed one month later.

Fitting for a movie that began life as a TV pilot, Clueless would eventually be turned into a TV show. It debuted on ABC’s TGIF lineup for its first season before moving to UPN for two final seasons. Some cast members made the jump from the film to the show, but Silverstone was replaced as Cher by Rachel Blanchard.