Clueless director Amy Heckerling on how a pessimist created one of cinema’s great optimists

As if! With those succinct words, Amy Heckerling launched a phenomenon that would grow to include not only a hit film, but a TV series, a musical, a comic book, and a series of young adult paperbacks—not to mention a million knee sock/plaid skirt combos. That phenomenon, as anyone who was a teenage girl in the ’90s surely already knows, is Clueless, Heckerling’s affectionately satirical 1995 take on Jane Austen’s Emma. Alicia Silverstone stars as Cher Horowitz, a precocious matchmaker at a tony Beverly Hills high school whose attempts to meddle in the love lives of her teachers and her peers eventually lead her to a stunning realization: She’s the one who’s totally clueless!

Clueless wasn’t Heckerling’s first teen-movie hit; she made her feature directing debut with 1982’s Fast Times At Ridgemont High, written by Cameron Crowe. That film is best remembered for three things: Sean Penn’s uber-stoner Spicoli, a sensitive and nuanced depiction of abortion, and a nude scene that wore down VHS tapes around the globe. Compared to that messy bundle of real-life contradictions, Clueless is a more escapist vision of high school life, driven by colorful fashions, highly quotable dialogue, and Cher’s indefatigable optimism.

But even though she created Cher, Heckerling, an incurable pessimist, still doesn’t get the whole “looking on the bright side” thing. We connected with Heckerling over the phone in advance of Clueless’ 25th anniversary (and a new Blu-ray release coming July 21), discussing the development of Cher, Heckerling’s fatigue about being asked, “What’s it like to be a woman in Hollywood?”, and the origins of the most savage insult in teen movie history: “You’re a virgin who can’t drive.”

Amy Heckerling: All right, I guess.

AVC: That’s pretty good for nowadays.

AH: “All right” is actually pretty stellar for nowadays.

AVC: When did you write the first draft of Clueless?

AH: I wrote a pilot with the character [of Cher], then the studio and the people that were there were replaced by other people, and they passed on it. Then I got a new agent, and he read it and said, “this would be a great feature.” All of that wasn’t really leading to a first draft of the film, but it was that character.

This must have been, I don’t know, in ’93? ’94? Everybody was drinking Snapple at the time, that’s what I remember.

AVC: There’s a line about Snapple in the movie!

AH: Well, the whole thing was written on the green iced tea.

AVC: Did you go through a lot of drafts with this script? It has so many quotable lines—“you’re a virgin who can’t drive” has become iconic.

AH: That was in the first full-length version of the script. I mean, that’s who I am, so that was always in there.

But the drafts—we had the TV pilot, and then the film, and then the TV series, and then the off-Broadway version—basically, if I stacked them up, they would reach to the moon. Once you start shooting, there’s pages, right? And they come in a different color [when you change the script]. We went through every color that there is, twice, at least. Only an AD would get that. [Laughs.]

AVC: Clueless could easily have been a really vicious satire of teen culture and rich kids. But there’s a lot of earnestness in, and affection for, your characters. What made you go that way?

AH: Well, that wasn’t a conscious choice. That was obvious to me. What I really wanted to write was a character who would be just completely optimistic, who would never think that anybody didn’t like her, or that things wouldn’t turn out.

And that just blows my mind. Rich or poor, there are people that have that optimism, and I don’t understand it. So I wanted to deal with that. There are characters that I totally love—one was written by Cameron Crowe in Fast Times, with Spicoli. It wouldn’t occur to him that he’s being the bad boy in the class when he’s ordering pizza, or doing whatever he’s doing. There’s no evil in him. It’s just, “This is fine and nobody will be mad at me for this.”

Another character I love is in the movie Ed Wood. He’s just so happy about what he’s creating, and it doesn’t occur to him that everybody thinks it stinks. Another big influence was in Gentlemen Prefer Blondes—not the movie, the book—and the character of Lorelei Lee. She just assumes that all men are in love with her, and goes through life based on that assumption. It’s adorable, I think, when you’re in your own pink bubble. That’s what interested me.

AVC: Do you feel like you understand those people better, having written those characters?

AH: Optimists or rich kids?

AVC: [Laughs.] Optimists.

AH: No. Recently I was working with somebody who was just thinking all the time about how things would work out. And I was just like, “What? How do you wake up and feel like this all the time?” I don’t get it.

AVC: It’s like, “Oh, that must be nice for you.”

AH: [Laughs.] Yeah, I’m watching The King And I with puzzlement, like, “huh.”
Sometimes you see it in little kids. And it’s just so endearing when it never gets knocked out in them.

AVC: Between doing Fast Times and Clueless, was there anything that you noticed that changed about teen culture in the meantime?

AH: Well, I wasn’t some sort of anthropologist looking through a microscope. Those were very different pieces of material, because Cameron Crowe went to a very specific school. It was working class, not big city kids. And he just recorded everything, and it was amazingly real. I don’t think a lot of people have read the book that the film is based on, but it’s wonderful. If they didn’t have a fast-food job, they weren’t going to be able to get a car—that’s what attracted me, the idea that because of the economics of their situation, they had to be more like grownups. And that’s kind of sad when you want to have a little bit of a freewheeling youth, you know?

And then Clueless was based on the Jane Austin novel, so it’s more of a comedy of manners. Austen is so viciously wicked and funny, but it’s a different world. It’s like saying what’s the difference between a Cagney movie and a Fred Astaire movie.

AVC: One of the best things about Clueless is the commentary about the different cliques and subcultures at the school. Are there any modern teen subcultures that you find interesting?

AH: Teen culture is something you dip your foot into every few years, and it’s a whole new vocabulary, new concerns, new fashions, new everything. Years ago, it was a whole phone culture, now it’s all about social media. That’s where people seem to live. And now this pandemic is going to change things in another way.

I don’t know how they do what they do. You have to somehow find a way to grow up, find out what you like to do, and what kind of people you like to be with, with the world changing all around you.

AVC: Do you keep up with social media at all? TikTok or anything like that?

AH: I am not on TikTok, but I am on some things. In Hollywood, they won’t have an actor come in and read [anymore]. They’ll look and see how many followers they have. It’s scary. And I’m the kind of person that likes to be private—even though I’m talking to you. [Laughs.] I’ll tell you anything you want to know, but basically I’m not one of those people that goes, “Here I am in the park today. What a glorious day! Look at what I’m wearing. Today I’ve tried bangs, what do you think?” That’s not me.

So now, if you don’t have like hundreds of thousands of followers going, “You’re so beautiful,” they’re not gonna hire you. And if you’re not on these things at all, they’ll go, “You’re an old person, we don’t want you.” Anyhow, now you’re getting me depressed. [Laughs.]

AVC: You’ve been asked since the early ’80s, “What’s it like being a woman director?”

AH: The very first time I was ever interviewed, they came with a certain agenda of what they wanted to write, and wanted me to say the thing that would work in their article. At one point I had said, “Well, I don’t think it’s any different.” And then they sent me a copy of what they were going to print, and it’s like, “Well, it’s very different.” And it’s like, “Wait a minute.” By then it’s too late, but why even bother talking to me?

And also—you go to Hollywood, and you’re a female. There aren’t a lot of them. And you’re going to either raise the flag and try to have a battle with everybody, or try to get in there somehow and make them like you. Make them feel like you can do what men do without being pushy and showing off, so they won’t think you’re going to fuck up because you’re a woman.

When people come from some outside group, and they’re first breaking into different professions—this is horrible, but I think minorities will understand this, and by that I mean anybody that came from anywhere that isn’t the top people—you don’t want to be “too Jewish,” you know? You don’t want to be “too” whatever country or group you’re from. You want to fit in. The first wave of people that are trying to get something done, it almost seems subservient, or like you’ve got no balls, you know? But you have to just fucking get in there and not have them hate you at first.

There was no #MeToo then. I just wanted to fucking be a movie director. I wanted them to let me make movies, and I didn’t want to have to be the one leading the march so that we could all do it. I mean, I would want all of us to do it, but you have to fucking get in first.

That’s not going to be a very popular thing to say, and I’ll be worrying all night that I said it. But it was harder for the people who were trying to do this 40 years ago than it is now. Maybe not harder, but it was different. And the amount of people that are actually doing it even now—the percentage of women in the director’s guild—it’s frightening how much it hasn’t changed.

AVC: It’s so low, especially in films.

AH: Well, film is a dead art form to begin with. And I love films more than anything—not more than my family, but I love movies. My friend Martin Brest, who made Scent Of A Woman, his son was giving him grief for only caring about movies on the big screen and not wanting to see them on streaming. And I said, “You know, Marty, he’s right. This is the way of the future.” And then there’ll be a newer way of the future. But theaters are closing up all over New York. And it’s only going to get worse—that was before nobody wanted to be close to anybody. So imagine!

AVC: So when you started directing, you were like, “I just need to get in the door. I can’t deal with being the leader of a movement. I just need to get in.” Did #MeToo change the way that people talk to you about these things? Or is it the same old conversation as always?

AH: It’s, “What’s it like being a female,” blah, blah, blah. What wacky stories do I have to tell? “When you come onto a set, do they respect you?”

In Hollywood, the people that I hire are nice to me. But it wasn’t so great on sets in other countries. You want to know how far you have to walk to find a ladies’ room? It is a lot easier for a guy on a movie set, I think, at least when I started. Dumb shit like that. But whatever.

AVC: If Cher Horowitz was in high school today, what causes would she be fighting for?

AH: First of all, she’d want people to wear masks. There’s a wonderful T-shirt that says, “Science doesn’t care about what you think.”

AVC: She’d probably have a whole closet full of them, honestly.

AH: Yeah. The answer is, a lot of stuff. She would be for equality, equal pay, immigration reform, prison reform—the environment and climate change and evil corporations poisoning our food supply and the air and the water. I mean, boy, where do you start?

AVC: There’s a lot to fight for.

AH: There’s no end of shit that happens, and happens continuously, and keeps repeating.

AVC: Well, we brought it back around to depressing. [Laughs.]

AH: That’s why we need to see happy people!