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The Definitive Oral History of How "Clueless" Became an Iconic 90s Classic

On the 20th anniversary of the film, this excerpt from Jen Chaney's new book features discussions with the film's breakout stars and Hollywood veterans on the movie that became a fashion template and cultural touchstone.

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?

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.

Clueless Movie Poster

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."

Amy Heckerling: Sometimes you're working on things and you think, Oh, I have to write this, or I'd better look at my notes. And other times you just want to. That was how I felt writing Cher. I just wanted to be in that world, and in her mind-set. All of [the main "Clueless" characters] were in [the original TV show]. [Eventually] the TV people put it in turnaround. That’s when Ken Stovitz became my agent, and I showed him that pilot, and he was like, "This is a movie."

Ken Stovitz, Amy Heckerling's agent: When you get into business with someone, you find out what really is the home run, dream come true. And early on she told me about this project. So I said, All right — if I can do anything for her, I’m going to do what I can to get this made.

Amy Heckerling: Then Fox movies bought it from Fox TV…. During the development there was a concern that it was too much about one female, and that I should make Josh a bigger part, and he should be living next door, and his mother [should be] in love with her father. [Josh and Cher] weren't ex-stepbrother and ex-stepsister. They thought that was incestuous.

Twink Caplan: So we went into turnaround. And we started working out of Amy's house, actually.

Ken Stovitz: We couldn't get it going. What we submitted was the screenplay and [one of] the [Aerosmith] music videos [with Alicia Silverstone]. I told everyone it was a $13 million movie. I gave them the budget; I gave them Amy's track record…. We got rejected so many times it was a joke.

Adam Schroeder, "Clueless" co-producer and then president of Scott Rudin Productions: Teen movies were just not happening. It was almost like a relic of the John Hughes movies in the 80s.

Amy Heckerling: Everybody passed on it. Then Scott Rudin liked the script. That stamp of approval was enough for the town.

Barry Berg, co-producer and unit production manager: Just having [Scott's] name on the film meant so much to so many. It became an important film the moment he signed on to produce it.

Amy Heckerling: When Scott read [the script], his notes were pretty much what brought it back to the way it was [originally].

Ken Stovitz: Rejection can either be the thing that kills you or the thing that inspires you to just say, "I'm not going to take no for an answer." We chose to do the latter. We chose to say, "We know we've got something good here. We're not going to take no."

Once Fox had decided that "Clueless" should be a theatrical feature rather than a TV show, casting got under way.

Carrie Frazier, "Clueless" casting director at Fox: I brought in Alicia Silverstone — I sent Amy a videotape of a young actress [who] I felt was really terrific.

Amy Heckerling: I was watching an Aerosmith video of "Cryin'." That was the first video she was in. And I just fell in love with her. Then my friend Carrie Frazier said, "You have to see this girl in 'The Crush.'" And I was like, “No, I want the Aerosmith girl.” Well, it was the same girl.

Carrie Frazier: That is exactly what happened — totally.

Amy Heckerling: [Alicia] came in with her manager at the time. She was like 17, and she was just so adorable and sweet and really innocent.

Alicia Silverstone, Cher: I remember when I read the script the first time, thinking, Oh, she's so materialistic — that I was judging [Cher] instead of being delighted by her. I remember thinking, This is so funny and I’m not funny. But once I was playing her — I just had so much fun being her. I loved how seriously she took everything. That's essentially how I played it…. I felt like that was [who] Cher was. She was so sincere and so serious. And that’s what I think makes her so ridiculous and lovely all the time.

Carrie Frazier: After Alicia did [the] screen test, as I remember, it went to Fox and they were kind of like, "Oh, she's O.K." You know, it wasn't like "Oh my God, this girl's fabulous." I was like, "This is the girl! If you don't grab her, you're nuts."

Amy Heckerling: I had my heart set on Alicia. [But] Fox … wanted me to explore all the [options]…. I saw Alicia Witt, the redheaded [actress]. And who else? Tiffani Thiessen. The one that — she was in that show and she cut her hair and everybody was mad? Keri Russell, yes. Then they go, "You've got to see the girl in [Flesh and Bone]." I never got to see her. I guess she was off on other things. That turned out to be Gwyneth Paltrow.

Carrie Frazier: It was the first time I'd seen Angelina Jolie…. But she was too knowing for what was needed for Clueless. Angelina never came in [to audition] for the project. I was just looking at her tape. I remember an agent pitching her, and I’m going, "No, no, no, this is exactly the opposite of what I need for this." Later on, when I started heading up the casting department for HBO, and I got the script for Gia, I said, "I've got the girl." That was Angelina.

Amy Heckerling: I met with Reese [Witherspoon] because everyone said, "This girl's amazing. She's going to be huge."

Carrie Frazier: I had [Amy] meet Reese over at the Four Seasons hotel in Los Angeles, on Doheny, in the bar.

Amy Heckerling: I saw some movie where she had a southern accent. Maybe it was on TV, a movie of the week. But I did see some scenes of hers and went: Wow. She's amazing. But Alicia is Cher.

Carrie Frazier: So much of casting is about catching the actor or actress at the right time in their life. And even though you end up going, "So-and-so can do the role," there was something about Alicia that was a little bit younger and a little bit more naïve in a way that we felt was really the right girl.

I brought in [Brittany] Murphy. She was just so similar, again, to the character. She was really sweet. Who else did I bring in that ended up in the movie?

Amy Heckerling: Ben Affleck told me [later that] he read. But I don’t remember that. He might have read for a casting director.

Carrie Frazier: I brought in Ben Affleck, for the role of Josh. I thought he would be fabulous for it. I was really trying to get Ben Affleck the part. Then, when I got the call that it was going over to Paramount, they wanted to have me work on it for no money…. And I said I wouldn’t do that — they'd have to pay me, and they said, "Oh, well, we really can’t do that." I was heartbroken about that on every level.

When "Clueless" eventually landed in the hands of producer Scott Rudin and Paramount Pictures, Frazier was off the project, and Marcia Ross was brought on as the new casting director. With Ross, a new set of producers — including Rudin, Adam Schroeder, Robert Lawrence, and Barry Berg — and Heckerling, Caplan, and Paramount executives all now at the decision-making table, the second attempt to cast "Clueless" began in the fall of 1994.

Amy Heckerling: [Casting Josh] was the hardest. I had a vision in my head and it wasn’t jelling with people out there. When I’m writing, I usually have little pictures of what I imagine the guy looking like. And I had the Beastie Boy: Adam Horovitz. There was something smart and funny about him.

Marcia Ross, "Clueless" casting director: Because I was always reading actors, I knew a lot of young actors, and I was able to come up with a bunch of thoughts for parts and sort of come in with ideas and show her.

Paul Rudd was one of those people.

Paul Rudd, Josh: When I auditioned for it, I had also asked to read for other parts [including Christian and Murray].

I thought Murray was kind of a white guy wanting to be black. I didn’t realize he was actually black. Also I thought: I haven’t seen that character before, the white guy who’s trying to co-opt black culture. But, well: that character is actually going to be African-American. Oh, O.K.

I think I read for Elton as well. But Amy said, “What do you think of Josh? Do you want to read for that?” So I did.

Amy Heckerling: I remember I saw Paul, and I really liked him. There were still more people to be seen [though].

Adam Schroeder: He needed to be older, and [Alicia] was young, but we didn’t ever want it to feel not natural when they ended up together. There was the whole stepbrother thing, even though they weren’t related at all, so we really wanted to be careful and cast that perfect person. We read a lot of actors.

Twink Caplan: Amy and I loved [Paul] right off. He hadn’t done that much, but he was cute and he was sweet. He reminded me of George Peppard. Not in his acting, but the nose. He was very engaging.

Adam Schroeder: We tested him, and we knew he was very, very top-of-the-list.

Paul Rudd: I knew that they must have been kind of interested, because they had me back a few times. Honestly, what I remember when I was auditioning and meeting Amy for the first time is making some joke about Shakespeare preparing something from a monologue. I’m sure it was not a very good joke or anything. But I remember she really laughed at it. Almost more than anything else, I remember, in talking with Amy in the auditions, I was like: Oh, she’s cool. I click with her.

Marcia Ross: We had him on hold for a long time, but they weren’t really ready to decide. Then … finally, they decided — they cut him loose actually. And it was hard. They really liked him, but they just couldn’t commit to it, and he was offered another movie. He took this Halloween movie. I remember he cut his hair for that.

Paul Rudd: That Halloween movie was my first movie, which I wasn’t so sure I wanted to do. I had a manager at the time who was like, “You should do this.” And then I remember I got "Clueless," and he’s like, "You shouldn’t do this." That's how good that manager was.

I remember really vividly where I was, just kind of walking down the street, and I was like, “Man. I don’t know. Why don’t I just cut off all my hair?” And I just walked into a barber shop and they just buzzed my head. Then, I want to say a week later or something, I was in a restaurant and Amy Heckerling was there.

Amy Heckerling: I went, “What the fuck did you do?” He said, “I didn’t think I had the part.” I said, “Oh my God, hardly any time went by — I didn’t finish seeing everybody. Yeah, I want you. You cut your hair?”

Paul Rudd: I was weirdly cavalier about it. In a way, it wasn’t really on my radar. And I remember I said, “Well, you know: if it’s supposed to work out, it’ll work out.”

Marcia Ross: We kept seeing more people and [were] not sure we had it….

I’m fairly sure Zach Braff read for Josh. I had hired a casting director in Chicago to put people on tape for the role while I was still searching for an actor to play the role. He was going to [Northwestern] at the time. My note was that he was good.

We screen-tested several guys with [Alicia] on film, and she and Paul — he really was good with her. From the minute he came in to the minute he got the part — and it was such a long journey, really, that one in particular — there was always this sort of harking back to: remember Paul? I can’t explain it to you. He never went out of consciousness.

Paul Rudd: I don’t remember the actual call saying I got the part…. I wasn’t sure about [Halloween]. But Clueless: no, I wanted to do that one.

Read the full oral history of "Clueless" on

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