June 3, 2023


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How Amy Heckerling Made the Ultimate Teen Movie

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Clueless was a teen movie 180 years in the making. When it was released in July of 1995, writer-director Amy Heckerling’s high-school comedy—which was based on Jane Austen’s 1815 novel Emma—took a classic story about a privileged, matchmaking teenager and gave it a high-octane upgrade, updating the story to 20th-century Beverly Hills and overhauling Austen’s characters with thoroughly modern makeovers.

The movie was a hit at the box office and with critics, and it made bona fide stars of its cast, including Alicia Silverstone as Cher Horowitz, Stacey Dash as Dionne Davenport, the late Brittany Murphy as Tai Frasier, and Paul Rudd as Josh Lucas. It’s real impact, however, took much longer to see.

she's a full on monet

In the quarter century since its release, Clueless has become a cultural touchstone. The fashion and language that the movie introduced became instant classics, and the movie remains a nearly constant reference, popping up everywhere from the red carpet (like when Lupita Nyong’o dressed as Dionne for Halloween in 2018) to TV (Killing Eve’s Villanelle used Cher Horowitz as a nom de guerre in the show’s second season) and fashion runways (where tiny handbags and plaid skirt suits pop up time and time again). The movie also spawned a 1996 TV spinoff, a 2018 Off-Broadway musical, and any number of rumored reboots and reimaginings.

stacey dash and alicia silverstone in clueless, 1995

Stacey Dash (as Dionne Davenport), and Alicia Silverstone (as Cher Horowitz) in the movie “Clueless”, written and directed by Amy Heckerling, 1995.

CBS Photo Archive

Today, Heckerling is firmly ensconced in the streaming era—she directed the new series Royalties, currently streaming on Quibi—but has never stopped thinking about Clueless. Here, she and a collection of collaborators, friends, and fans look back at what made the movie special, and why we’ve never been able to forget it.

The Beginning

Amy Heckerling’s first feature film was the 1982 hit Fast Times at Ridgemont High. She went on to make comedies like National Lampoon’s European Vacation and Look Who’s Talking, but never stopped thinking about setting another movie at an American high school.

Amy Heckerling, writer and director: You don’t go, “you know what, the world needs an adaptation of Emma and mine will be genius.” You find yourself driving around wondering, what am I going to do next, and thinking, I stink, and everybody hates me. Then you start to wonder, what do I like and what makes me happy? When you work on something in the movie industry, or that industry as it existed, things take a long time. You really had to want to do what you were working on. I started to think of what really amused me, which was very positive characters; I just don’t understand how people can go around being positive and it kind of cracks me up.

he is kind of a baldwin

Mona May, costume designer: I worked with Amy Heckerling on a pilot that didn’t get picked up, but we fell in love with each other because we had the same kind of artistic sensibility. When she wrote Clueless, she knew that I was the person to do it. I grew up in Europe, so I had a very European point of view. And she knew that because I also studied fashion, I got into costume design that married high fashion and the costume design—I could bring the high-fashion from Europe to high school in Beverly Hills.


Brittany Murphy (as Tai), Alicia Silverstone (as Cher Horowitz) and Justin Walker (as Christian).

CBS Photo ArchiveGetty Images

Heckerling: I started to think what if there was a teenager girl who, no matter what was happening, couldn’t have her bubble burst. I was wondering about this particular character, what are the best bones for a three-act feature, and I remembered I had read Emma in college. Then I re-read it, and everything in it was so perfect and so relatable in that time period—or any time period, really, because she’s so wise—that I started to think of what the equivalent would be in the world I was living in, in California in the 1990s. How could I turn that into a teen comedy for the present time?

clueless whatever

Autumn de Wilde, director of Emma: Because I was in my twenties, I probably ignored it at first. And then when someone I knew liked it, I was like, “I’ll check this out.” I first heard about it because I got a postcard from Stephen Malkmus, the lead singer of Pavement, that said that he watched Clueless on the plane or maybe right before he got on a plane—and he didn’t expect to like it as much as he did. I remember getting that postcard going, “Stephen Malkmus liked Clueless?” And then I was like, “OK, I better watch it.”

The Impact

Clueless was a certified hit, making a reported $56 million in ticket sales, but its impact went beyond the big screen. The movie tapped into a hunger for smart content aimed at young people–something Jane Austen had mastered—and offered a depiction of teenagers that was exaggerated but not untrue, something which audiences couldn’t help but appreciate.

Bridget Gless Keller, philanthropist, jewelry designer, L.A. native: I was a film major at USC, and there weren’t a lot of very visible female filmmakers at the time, so of course I paid attention to Amy Heckerling. She had done Fast Times at Ridgemont High, the definitive 1980s high school movie, and then she made Clueless which did the same for the 1990s.


Paul Rudd (as Josh) and Alicia Silverstone (as Cher Horowitz).

CBS Photo ArchiveGetty Images

Autumn de Wilde: Amy not only loved Emma, but she knew it. She understood the point of view and she understood the history, so she was able to rework the story in a way that makes you, if you know the book, recognize it. But if you don’t know Emma, you totally get it and you can relate to it even if you’re not that rich girl or that girl that got the makeover or the stoner skater boy. That’s a real testament to Amy Heckerling’s brilliance.

Bridget Gless Keller: I went to the Marlborough School, an all-girls school in L.A., and we partied with people from Beverly Hills High, it’s where I took driver’s ed. And this movie is so close to the truth; yes, it’s big, broad brushstrokes but it wasn’t so far off. The clothes were just a little more fashionable in the movie than they were in real life. But when they broke down all the different groups—the stoners, the fashion crowd, the kids who were into film—that was all true.


Breckin Meyer (as Travis Birkenstock).

CBS Photo ArchiveGetty Images

Autumn de Wilde: I didn’t really ever like high school. When grown-ups try to tell teenagers how they feel or try to tell them what their opinion of their modern life is, it rarely works. But because Amy Heckerling was actually cool, she knew how to poke fun at all of it, but not from a square, grown-up point of view.

The Lexicon

“As if.” “Whatever.” “You’re a virgin who can’t drive.” Clueless didn’t only mimic the vernacular of L.A.’s one-percent teens, it also introduced a new brand of language to audiences worldwide—one that you can still hear echoes of today.

clueless whatever

Amy Heckerling: One thing I love in movies is the language. In My Fair Lady, what you say defines everything about you—how much money you have, where you grew up, everything. I wanted to incorporate that in a goofy way and also mix it up. I wanted white kids to be using words they learned from rap artists, black kids to be speaking Yiddish, a young person talking like he’s a Rat Packer, or a girl who’s a father is a lawyer using legal terms. We could have fun with that.

Every time you put in a line of dialogue you’d drive yourself crazy thinking of the words you might use, so I put together a dictionary of words I might like—good, great, happy, bad—and had a million synonyms at my disposal, it’d be like having a perfect thesaurus for my purpose. I still have it, and for a few years, I just kept adding to it. Now that everything’s online, there’s no point to it. I did it through the early 2000s but now you can just use Google.

you're a virgin who can't drive

Bridget Gless Keller: Think about how “as if” became part of our lexicon. Amy took a sample of Beverly Hills life and introduced it to the rest of the world. At that time, I wasn’t using phrases like “as if” or “whatever,” but it was happening. Amy took these phrases that a small group of people were using and put a spotlight on them, then the rest of us started using them. “OK, so he’s kind of a Baldwin” or “she’s a full-on Monet,” those are still funny.

The Fashion

From Cher’s iconic yellow Dolce & Gabbana suit and Calvin Klein slip dress to Dionne’s outlandish hats and the throwback looks of Justin Walker’s character, Christian Stovitz, the movie doubled down on serious fashion and managed to not only send up its characters, but set trends that are still going strong today.

Mona May: Amy wanted to make sure that this movie was young and youthful. So, the high fashion is almost transmuted through their eyes. They are young and sweet; she didn’t want models running in the hallways. Cher’s yellow suit will always be something so iconic. And it was so interesting trying to find that right outfit for that opening scene of the movie. What was it going to be that makes her pop? We’ve tried a bunch of different things, and nothing really worked. But once we had the yellow the Dolce & Gabbana suit, it was just that a-ha moment.

Stefano Gabbana, fashion designer: It was 1995. The world was very different, but the impact of Amy Heckerling’s film was viral even without social media. An ironically intelligent movie that, between stereotypes, outlines a perfect picture of the “millennial” generation of the time. It would be interesting to watch it today, with our “millennials”; maybe we would discover that things have not changed so much!

Mona May: It was so interesting, the whole process, because Alicia Silverstone’s character Cher had 60 changes in the film. It was a huge undertaking, and there was not a big budget. I had to be clever in creating these looks. And as a costume designer, I think what’s really important is to really create the characters. When we were starting to research and going to high schools, it was all grunge—baggy pants, oversized shirts, and plaid for boys and girls. And, so the inspiration really had to come from Europe. We had to see what we could buy, scrounge, or borrow. We couldn’t make calls and just go, “Hey, we’re doing this movie, can you send a bunch of stuff?”

Domenico Dolce, fashion designer: In the film, there are many references to fashion; Cher’s passion for shopping is comparable to that of Carrie in Sex and the City. Seeing our creation on the big screen is always a great emotion. 25 years ago, it was a dream come true!


Brittany Murphy (as Tai), Alicia Silverstone (as Cher) and Stacey Dash (as Dionne).

CBS Photo ArchiveGetty Images

Amy Heckerling: People are always sending me stuff—look at the screening they had there, or the people dressed up here.

that was way harsh, tai

Mona May: We had to find somebody who knew who the contact to Alaïa to get that dress. Then could we borrow the dress, and could we make alterations to fit Alicia. Then can we still return it? It was a lot more footwork that if you now just send an email to a PR firm and get a bunch of clothes. But then, you see the actor putting something on and you almost have goosebumps knowing that this is it. The character is born in that moment. It’s just phenomenal.

The Legacy

Twenty-five years after its release, Clueless is just as powerful as ever. The story has been adapted for TV and the stage—there was an Off-Broadway musical, and in 2019, a group including Issa Rae, Kumail Nanjiani, and Ilana Glazer performed a stage reading at a San Francisco comedy festival—and last year’s remake of Emma reminded us all of how current the story can feel even when it’s set more than a century in the past.

Autumn de Wilde: I actually watched Clueless this weekend. I didn’t watch it right before I made Emma because I didn’t want too many echoes in my head, but I had obviously seen it quite a few times because years later it became like comfort food. I’m obsessed with teen movies. I was talking to a friend about it and said, “Why is it no matter how old you get, you always want to watch a teen movie?” And I remember him saying, “I don’t remember what I was so upset about in my twenties, but I remember every single person that hurt my feelings in high school.”

alicia silverstone in 'clueless'

Alicia Silverstone holding shopping bags in a scene from the film ’Clueless’, 1995.

Archive PhotosGetty Images

Mona May: I was at an art fair earlier this year, and there was this adorable young girl, maybe 15. I said, “Oh, I just love your outfit. It’s very Cher.” And she said, “I love that movie.” I told her I designed the costumes, and she almost fainted. She was just so happy to meet me.

Domenico Dolce and Stefano Gabbana: Today, Cher Horowitz would be the perfect influencer!

Amy Heckerling: Did you see the Off-Broadway musical? I wrote that. I was just talking to a producer the other day, we’re revamping things and it’s possible it will be in another country to begin with. Clueless is kind of my happy place. I never really let go of it completely. The stage is where my brain is. Apparently, there’s going to be a TV show, more of a Riverdale take on Clueless. My ex-boyfriend from film school has had three of his films rebooted, and he always says you just have to let it go. It’s just material, you were paid for it, the studio owns it, they can do what they want. What can I say? It pays for the Fresh Direct.

clueless buggin

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