Twenty Years Later:

Why Clueless Endures

Two full and tumultuous decades in American culture have passed since the summer that Clueless burst into theaters. But the platform-shoe prints of this comedy of nineties manners can still be seen all over popular culture.

In every TV show and movie that adopts a young-skewing female point of view—Pitch Perfect, HBO’s Girls, New Girl, The Mindy Project, Suburgatory (especially the episodes that reunited Alicia Silverstone with Jeremy Sisto), and others—hints of Clueless can be found. Its influence can be seen, too, in the myriad modernized Jane Austen tales that followed in its wake, including Bridget Jones’s Diary, The Jane Austen Book Club, Bride and Prejudice, the Hindi rom-com Aisha (which is far more Clueless than Emma), Austenland, and The Lizzie Bennet Diaries.Clueless deserves to be much, much more recognized for its influence on popular culture related to Austen,” notes Austen scholar Dr. Juliette Wells.

On social media, the Clueless effect has resulted in scads of Tumblrs fire-hosed with “As if” GIFs or branded with names like “In Cher Horowitz We Trust”; Instagram feeds filled with Clueless screen shots or ladies dressed in Cher-wear for Halloween and New Year’s; and tweets peppered with Clueless quotes or, in the case of the @modernclueless Twitter feed created by writers Jessica Blankenship and Ella Cerón, devoted exclusively to 140-character, Cher Horowitz–ian interpretations of current events. That account, by the way, has more than twenty-eight thousand followers. (Sample tweet: “Cher: I’m captain of the Ebola epidemic relief. Mel: I don’t think they need your skis.”)

The fashion choices, music videos, and/or social media profiles of some of the biggest contemporary pop stars—from Charli XCX to Rihanna to Katy Perry to Iggy Azalea—point to a continued Clueless fixation, as do the number of Clueless-related blog posts, listicles, and quizzes that pour forth on the regular from outlets like Buzzfeed, Bustle, Jezebel, and (yes) Vulture.

Pretty soon, the Clueless legacy may make its mark on a new cultural frontier: the stage. Amy Heckerling has written the book and lyrics for a long-gestating musical version of Clueless. At the time this is being written, the Dodgers—the play-producing team behind Broadway hits such as Matilda, Jersey Boys, and Urinetown—are in the process of signing on to produce; Kristin Hanggi, who directed the original production of Rock of Ages, is on board to direct; Clueless composer David Kitay has been working on some of the musical arrangements with Heckerling; and the aforementioned Katy Perry has expressed interest in playing Cher, though, at this pre-publication moment, that’s not a done deal. “It’s a jukebox musical, so it’s got songs from the past,” Heckerling says. Kitay adds, “It’s really a totally original slant on that that I don’t think anybody’s ever done before.”

Clearly Clueless isn’t going anywhere. Which raises a question that was posed during just about every interview conducted during the writing of this book: what makes this movie so enduring?

In keeping with the complex mix of satire, broad comedy, cultural commentary, and earnest teen romance at work in the movie itself, there are multiple answers to this question.

In the book X vs. Y, a back-and-forth exchange of pop cultural arguments written by sisters Eve and Leonora Epstein, the X-er, Eve, suggests that Clueless appeals to her generation as well as her younger sister’s because the relationship between Cher and Josh is essentially “the story of Generation Y (Cher) falling in love with Generation X (Josh).” I heart this idea hard.

There’s also the notion that the movie’s fantasy captured certain elements of our future reality, which gives Clueless a currency and timelessness that other teen movies lack.

Taking that a step further, I also offer this: Clueless operates on a level that mirrors the way we process information in the era of digital media. We are all reinventers now. We immediately turn TV moments into GIFs, filter our Instagram photos so they’ll look more evocative, post our own versions of movie trailers on YouTube, even, in extraordinarily rare cases, self-publish Twilight fan fiction that goes on to become bestselling works of mainstream erotica. Every piece of pop culture we encounter is an opportunity for reinterpretation.

As music supervisor Karyn Rachtman implied, Clueless is steeped in a nondigital version of that kind of updating. It samples from preexisting things—Emma’s story structure, slang from the UCLA dictionary, nineties pop culture references, schoolgirl plaid, seventies and eighties pop songs, the iconography from other movies—then reworks them in a way that creates something totally new, different, and original.

Clueless was at the forefront in so many ways. And for so many reasons, that’s very likely where it will continue to stay. Not “as if”; for sure.

Adam Schroeder, coproducer: I keep on thinking, Wow, it’s such an old movie and I wonder, Does it feel dated? But whenever I talk to friends with kids, or relatives and [their] kids, they all have discovered the movie in the last twenty years and it kind of plays just as if it were contemporary, even with twenty years having gone by.

Alicia Silverstone, Cher: It was always a movie that spoke to many different generations. I remember when it came out, parents really loved it. Because, you know, they had to see it with their kids three thousand times and they would say, “Actually, I really like that movie.” Amy makes movies for both. It’s got all the young teenybopper things going on but it’s also got super-clever ideas spread through there as well.

Danny Silverberg, second assistant director: I’ve got kids. They’re not young anymore, but they’re twenty and seventeen. They have seen the movie a dozen times. I didn’t even realize that. My daughter told me, “Oh yeah, we watch this all the time.” It’s a sleepover movie, when friends come over after school—they’ve seen it over and over again.

It’s still very relevant to what teenagers are doing.

Sherry Lansing, former chair and CEO of Paramount Pictures: Much of who you are as a young girl is still who you are as an adult, even though you’ve had experience. But I think for women—and maybe for men as well, but I can only speak for myself—we all remember that and it still strikes a chord for us. Here I was, clearly not the demographic, but it turns out that the demographic was everybody.

Alan Friedman, makeup supervisor: I have a wedding business [doing makeup] up in Northern California, in wine country. And I can’t tell you how many times I will go to a location to work with a group of young ladies and that’s been part of the festivities. If there hasn’t been a male stripper getting naked, there’s certainly been Clueless on disc.

Bill Pope, director of photography: Like Amy and the fountain in Gigi, there’s something that touched [fans]. And it goes right into their iconography.

Charlie Lyne, director of the teen movie documentary Beyond Clueless: What Clueless really did in my eyes, in terms of restoring faith in that [teen] genre, was show that there was a market for films that were very fiercely set in the here and now and felt like they were for actual teenage audiences.

Sarah Pitre, director of national programming, Alamo Drafthouse, founder of the Girlie Night movie series: It’s also super nostalgic for those of us that were in high school in the nineties. To me, it’s like a guilty pleasure without the guilt because it does have substance and it did make an impact on our culture. I have a ton of guilty pleasures and I’m not ashamed of them. But I would never call Clueless a guilty pleasure. It’s just a freaking good movie.

Stacey Dash, Dionne: It was the first of its kind. They tried to do some [teen movies like it] after that but, I feel, failed. They never got it just right like Clueless did.

Amanda Hess, writer, Slate: Clueless . . . has so many smart things to say about consumerism, I think, and it is really kind to its characters even when it is mocking them. I think especially for someone like Tavi [Gevinson] or the people who are in her community that she has created, they really are drawn to that. They’re still really in this teen world that, in a lot of ways, is like ruled by this consumerist culture. There are parts of it that they want to engage in and parts they want to push back against. That movie is like a great gateway for understanding how that might be possible.

Wallace Shawn, Mr. Hall: The movie is both a satire and, in a way, a sort of celebration of these characters. And I can’t really explain this, but people love it who see it as a satire, and people love it who see it as a celebration. Their actual feelings as they watch the movie may be not that different, I don’t know. It’s a sort of mysterious phenomenon.

Paul Rudd: The Breakfast Club and those movies were major movies to me and all of my friends, probably for the same reason that Clueless is major to some other people. They saw that movie at an age when it’s like, Oh, I’m that age and there’s not a lot of movies about kids my age that are like this. I don’t know what it is. But then they kind of grow up with a feeling of nostalgia. You know, you see it at a certain age and you like it. Then you see it a few times. I mean, [Clueless] was a multi-viewing kind of movie. I’ve met many parents that said, “God, we played that DVD in our house so much.” Or videotape, probably, at the time. It becomes a part of your childhood and then as you get older, you just have such warm feelings about something like that.

It’s an amazing thing to be in a movie that somebody is that passionate about, or has actually meant something like that to somebody. As to why, I don’t question why. But I certainly am appreciative [that] it does hold such affection for so many people.

Amanda Hess: That was the first Paul Rudd movie that I had ever seen and I think he definitely imprinted on me and other girls of my generation, where he became just, like, the ideal male actor. We’re all still following Paul Rudd’s career partly because of that.

Amy Wells, set decorator: It’s so funny because I’ll see Paul Rudd now, and I just cannot believe—how can someone continually be that gorgeous for an entire lifetime?

I worked with Jon Hamm, who’s a good friend of his, for a long time. I always said Jon Hamm was the most gorgeous creature on Earth. As I look at Paul Rudd, I realize: No. It’s actually Paul Rudd.

Michelle Manning, Paramount executive who oversaw production and also produced Sixteen Candles and The Breakfast Club: I think that what Amy Heckerling, Cameron Crowe, John Hughes—what they all did very well was talk to kids, because they were kids in their hearts. It wasn’t like: here’s what I think you sound like . . . It was: here’s what you sound like and here’s the issues that are relevant to you. I think that makes kids want to listen, you know.

[John and Amy,] they were both, at whatever age they happened to be—and probably still to this day, with Amy—they’re teenagers. I mean, they are teenagers. They would hang with the kids [on set] as if they were one of them. There was never a feeling of “I’m the director and the writer, so I’m the boss.” It was always like, “I’m just one of you and let’s hang out and let’s be teenagers together.”

Paul Rudd: One of the things that Amy does better than anybody is represent kids and teenagers and the stuff that they go through, but not talk down to them in any way. Because she loves kids and respects their thoughts about things, and what’s important to them, and their insecurities, and everything. I think she captures that in a really sweet way in this movie.

Jeremy Sisto, Elton: Amy is just a genius and [Clueless] was one of her amazing ideas. It’s pretty exciting to be a part of something like that, but it’s really—for me it feels like the thing that’s amazing about it is her. That she had this idea and she wrote the script and she created these characters.

Twink Caplan, associate producer and Miss Geist: Amy made a place for all of us, in a certain time, in an era that will never be forgotten, just like [George Lucas] did with American Graffiti. You know, there are those standout times that make you always remember you’re part of something so much bigger. You’re the face of somebody’s childhood, or just something that they’ll remember.

Jessica Morgan, cofounder and cowriter, Go Fug Yourself: I think that there are a lot of movies that are really funny in context, but you can take lines out of Clueless and it’s still amusing. Which lends itself to maximum real-life quotability. Regardless of context, “You’re just a virgin who can’t drive” is basically the meanest thing you can humanly say to a teenager.

Heather Cocks, cofounder and cowriter, Go Fug Yourself: There will never be a day when Jess tells me her foot hurts that I don’t reply, “Do you want to go to the nurse?”

Kate Schellenbach, drummer, Luscious Jackson: I also like the way it doesn’t put down anybody. Like there’s the stoner, but then he’s sort of included, and then there’s the gay kid who—there’s no gay slurs, which is kind of amazing.

For all of us who have kids and we’re constantly trying to find things on Netflix for them to watch . . . when you find something like Clueless, you’re like, “Thank God, it’s something I can watch with my kid.” I think we all get a little something out of it.

Jace Alexander, Mugger: I have three kids so I’m constantly looking for movies. They’re always saying, “Let’s watch a comedy, let’s watch a comedy.” Then I start scrolling through these massive lists of old comedies and I just scroll past all of them because they’re not really that good. They’re not really that funny, and they don’t make you feel good, most of them. This one has that little touch of magic to it, you know? It really does.

Dan Hedaya: I think there’s a purity to the movie. It’s clean-cut. It’s not vulgar. . . . Mostly, when I think about it, it feels like a very pure movie. There’s nothing cynical about it.

Paul Rudd: And Alicia’s so good in it. She just carries the thing. She’s incredible in it.

Elisa Donovan, Amber: Once in a while, when all the stars are aligned and all of the right people are involved, this beautiful thing happens. And I think that that is what happened with this movie. It doesn’t happen all the time. There are like a handful of movies that have that kind of longevity, especially for comedies, because comedies are so difficult to make.

Mona May, costume designer: Maybe to some people it would be silly to say, “Oh my God, you did Clueless.” To me, it’s very serious because it’s my work. It’s my own expression of my art. I will never feel tired of talking about it. I will always feel proud of it no matter what. My friends laugh that I’ll have a boa on my grave, you know. A pink boa on my grave.

Bill Pope: In the end, you’re left with exactly what Amy wanted you to be left with: you’re happy.

Amy Heckerling: I’m happiest when I’m in that sort of fantasy land. That happy, youthful, optimistic place where somebody can see what’s good in people and see what’s good in the world. Maybe you have to be an idiot to be like that. Not an idiot. But clueless.