The Definitive Oral History of How Clueless Became an Iconic 90s Classic (2024)

In mid-July of 1995—when American culture was fixated on such matters as O. J. Simpson’s ill-fitting glove—the fact that a modestly budgeted teen movie called Clueless was about to arrive in theaters, become a major box-office hit, catapult the careers of its stars, influence fashion for two decades, and become a permanent cultural touchstone for multiple generations … well, let’s just say it was something most people couldn’t have predicted at the time.

Executives at Paramount Pictures—the studio that took on the film after others had passed on the project—had great confidence in writer-director Amy Heckerling’s comedy about a shopaholic Beverly Hills teenager with a few Jane Austen DNA molecules in her genetic code. Sherry Lansing, then the head of the studio, liked it so much that after screening it she didn’t have a single story note.

It’s not as if Clueless had been flying entirely below the public’s radar. The comedy benefited from some serious promotional juice courtesy of MTV, which, like Paramount, was part of the Viacom family and pitched the film heavily to its Real World-addicted Gen X and Y audience. Media buzz about the breakout potential of Alicia Silverstone—then best known for her appearances in a trio of Aerosmith videos and the thriller The Crush—also started to build well before the film’s release. But in Hollywood, even a gorgeous, on-the-rise young starlet and a director with a track record for making profitable hits (see Heckerling’s Fast Times at Ridgemont High, European Vacation, and the Look Who’s Talking films) do not guarantee success.

Then Clueless made its debut, on July 19, 1995, and became the No. 1 movie in the country that day. The weekend of July 21–23, it generated $10.6 million and immediately was branded as one of the summer’s most unexpected triumphs. The movie went on to earn $56.6 million in the U.S. and Canada (a figure that the movie data-tracking site Box Office Mojo equates to $105.7 million in contemporary, inflated dollars). That’s a nice return for a film whose production budget was $12 to $13 million.

More important, Clueless touched a chord in the culture that was clearly primed and ready to be struck. Pre-teen and teen girls raced to malls in search of plaid skirts and knee-high socks. Almost immediately, Paramount began working with Heckerling to develop a TV adaptation. Within a year, the movie’s soundtrack would sell enough copies to be certified gold, and would eventually reach platinum status. The success of Clueless also would defibrillate the barely breathing high-school movie genre, resulting in a flood of teen movies in the late 90s and early 00s.

What’s even more remarkable is that, 20 years later, Clueless is still as omnipresent in American culture as it was back then. Thanks to its presence on cable, DVD, and streaming services such as Netflix and Amazon Instant Video, Clueless is still watched on a regular basis by longtime fans as well as young people discovering the film for the first time. Tributes to the movie—in the form of Twitter accounts and Buzzfeed listicles—are ubiquitous in the digital sphere. Fashion designers and labels continue to riff on the costumes created for the film by Mona May.

The idea of molding Jane Austen’s narrative structures and themes into something more modern? That has been everywhere post-Clueless, from Austenland to Web series such as The Lizzie Bennet Diaries and Emma Approved. The influence of the film can be seen in the pop-cultural creations of some high-profile influencers of today’s girls and young women, including Katy Perry, Lena Dunham, Tavi Gevinson, Mindy Kaling, and Iggy Azalea, just for starters.

Clueless, then, isn’t merely a touchstone for the 90s generation. It’s a teen movie that continues to be passed from one generation to the next and is just timeless enough for every generation to think it’s speaking directly to them.

So, how did it all happen*?*

How Clueless Got off the Ground

In 1993, Heckerling began developing a TV show for Fox that focused on the popular kids at a California high school, including a central female character fueled by relentless reserves of optimism. At that point, the project was called No Worries, one of several names used (I Was a Teenage Teenager was another) before Clueless got its official title. Given Heckerling’s established skill and success with coming-of-age comedy, it seems as if No Worries should have easily come together. But that wasn’t the case.

In its formative stages, the project eventually known as Clueless went from potential Fox TV show to potential Fox feature film, and then—for a short but frustrating period before landing at Paramount—almost didn’t happen at all. Its path to the big screen is a tale about a filmmaker inventing a very positive character, then dealing with frustration and rejection, but ultimately finding the support to make her movie by staying true to her vision.

Amy Heckerling, writer-director: I remember reading Emma and Gentlemen Prefer Blondes. Those characters: what I gravitated to was how positive they could be.

Twink Caplan, Miss Geist and associate producer of Clueless: After Look Who’s Talking, Look Who’s Talking, Too, and a couple TV shows that we tried to do [together], Amy came up with this idea of Clueless, that was a takeoff of Emma.