“I Never Felt Embarrassed”: Amy Heckerling on Making Movies About Teens and the Future of ‘Clueless’

The soft-spoken Amy Heckerling — usually clad in black, with unruly hair and kohl-rimmed eyes — exudes a New York City cool that’s reminiscent of an artist, not a woman who has written and directed some of the biggest blockbusters of the ‘80s and ‘90s. Beyond the comedy, Heckerling’s films have a sly edge that betray her past as a Bronx-born latchkey kid who spent her hours watching James Cagney movies on TV — an outsider looking in.

Fast Times at Ridgemont High remains an iconic portrait of teenagedom, featuring then-unknown A-list celebs at their scrappiest. Heckerling was the perfect filmmaker to direct Cameron Crowe’s sharp quips. Clueless is a touchstone for anyone old enough to appreciate its satire and anyone young enough to have obsessed over the film’s fashions and endlessly quotable dialogue. Her movies continue to find audiences more than 20 years later, and Heckerling’s recent projects, including Vamps and episodes of The Carrie Diaries and Gossip Girl, also invite discovery.

“I’m a loner and a weirdo,” Heckerling told me in a phone interview. “Martha Coolidge is better [at interviews] than me,” she said, referring to one of the directors featured in TCM’s Trailblazing Women series. Heckerling’s 1989 film Look Who’s Talking recently aired on the network, and the filmmaker will be co-hosting the “1990s Mainstream Hits” slate of movies by women debuting Tuesday night. Despite her self-described aloofness, Heckerling offered insight about her process, making movies before the age of the Internet, and more.

Amy Heckerling, Photo by John Nowak/TCM
Amy Heckerling, Photo by John Nowak/TCM

Flavorwire: I rewatched Nancy Savoca’s Valley Girl when it aired on TCM, and I was thinking of Fast Times. Both films are so different from most of the movies about teenagers that you see today. Fast Times, for example, had you dealing with abortion, drugs, and sex. What was it like trying to make a movie with these rarely touched upon subjects, particularly when it came to women?

Amy Heckerling: Actually, I don’t think they were rarely touched upon. I remember there was a movie, I forget the name of it, with a teenage girl who gets an abortion. I’m sorry, I can’t remember the name. And there was Last American Virgin, which I think was more serious than its title sounds. It had some realistic and sad moments in it. I felt like there was a lot of freedom and serious subject matter laced into these comedies or movies with high school hijinks.

What do you think about films today for teenage audiences, which largely consist of superhero movies, dystopian narratives like The Hunger Games, or paranormal romance stuff like Twilight? The latter two movies have prominent female leads.

I know that’s all the young adult literature. People say, “It’s good because it empowers the young girls,” and I’m all for girls being empowered, but I don’t know . . .  they kind of creep me out. The Twilight films . . . I don’t know. There’s something . . . icky. I don’t know if that is a good answer, though. They’re [popular movies about young women], and you can’t argue with that.

What are the essential components for you when writing or directing a movie about teenage girls or creating female characters?

If you’re writing about any character who is your leading person, you want to make them sympathetic and identifiable. Of course, anything about adolescence is going to deal with finding your place, your personality, and your identity. There’s a whole sexual awakening, too. There’s a lot of stuff to play with.

During your time at AFI, you made the short film Getting It Over With, about a girl who wants to lose her virginity before her 20th birthday. I’ve never had the opportunity to see it, but I know it helped open some doors for you. Was this the film that sparked your interest in making movies about teenagers? What were the ideas behind the movie?

At AFI people wanted to show that they could be directors. They wanted to have a really good calling card at the end of the day. They wanted to show how they composed beautiful shots, tell a story, and that they could direct actors. They were trying to be more mature. They didn’t want to show that they were kids. And I never felt embarrassed about that. I thought, “Those are the fun movies.” Growing up and seeing West Side Story and Bye Bye Birdie I thought, “Those are all for young people, and I enjoy watching them.” And I didn’t want to say, “Here’s a serious movie, based on a serious story, with serious crying scenes” to show that I know how to direct. That would never have occurred to me.

You made Look Who’s Talking when you were a new mother. Was the studio receptive to a movie about a single mom? As edgy as comedies were in the 1980s, it was pretty rare to find a movie about that subject, even in a comedic way.

The way the idea came to me was more from a male point of view. I always saw that movie through the baby’s eyes. I had a male voice in my head. I knew that I might not be in the position to get the world’s biggest, funniest movie stars to be in my projects, but I could certainly get them for a few hours to do voice work. So, I was trying to figure out how to make this film that would tell my story and what I was feeling, but in a way that would be enjoyable for guys.

'Clueless'
‘Clueless’

Clueless is the iconic Amy Heckerling movie, and it’s still part of our cultural conversations. You’ve said several times before that it was a movie of opposites for you — the light to your dark. Can you talk more about that?

I’ve always been kind of amazed at optimism. And thinking about what kind of characters I enjoy, I kept coming back to that kind of a person. I was wondering what would it be like if everything I worry about, think about, or do was the opposite. It was almost like I was living a Seinfeld episode where George does the opposite of everything. So I thought, “What if somebody yells at me, and I just think they’re amusing? What if I got out into the world wearing bright colors and assume that I look good?” It’s not the way I go about functioning, but what would happen? What would it be like for somebody to be like that?

Was there a lot of pressure on you to make another hit like Clueless? Did the expectations change?

There’s always that. Nobody says, “OK, now you can go do what you want.” That’s crazy. And if you did something that made a lot of money they go, “Why don’t you do one of those again?” That’s not how a creative person comes up with anything. That’s business thinking. You live inside yourself, and you still don’t know what you’re going to want to spend your time playing around with. You don’t know how people will respond to it. You just have to do it.

You started your career as an artist. You’ve always described yourself as a loner. But one of the most striking aspects of your career has been your commercial success, which is completely opposite from that kind of vibe. Still, you find ways to assert this more rebellious side of yourself in your work, which I appreciate. How do you juggle both sides of yourself creatively?

It’s weird that you would say “artist,” because I always feel funny even using that word. I went to art school — which they just tore down — and it was an amazing high school. It was the High School of Art and Design [in New York City]. All the kids there, 14 and on, knew they wanted to be artists. One thing that was apparent to me was that I was not as good as all of them. The connection between what was in my head and what came out of my hand wasn’t working.

You’ve never viewed yourself as an artist?

If you define anybody who works in any sort of artistic career as an artist, I always feel like that’s a funny word. You get too arrogant or something.

Tell me what you think about the Trailblazing Women series. Are there any favorite movies from the slate you co-hosted about ’80s films?

I just watched some of the documentaries last night, and that was interesting. I haven’t watched everything, but I watched the romantic comedies. I’m a big fan of Joan Micklin Silver. It’s great that they’re just showing so many of these female movies all together. It’s wonderful. And to see the people is fun for me.

Sean Penn in 'Fast Times at Ridgemont High'
Sean Penn in ‘Fast Times at Ridgemont High’

Has there been a woman filmmaker in your life who has been a mentor to you? That’s been a theme of the interviews I’ve done around the Trailblazing Women series.

I’m not really that type. As far as somebody giving advice or words of wisdom, I’ve known Mel Brooks for many years. But he’s not a woman. [laughs]

Has he talked to you about your experiences as a woman in comedy or Hollywood?

No, that’s not a concern with him. He’s worked with some of the funniest women — Terri Garr and Madeline Kahn. He has incredible respect and finds women funny.

You made European Vacation, which is my favorite in the Vacation series. What was it like working with Chevy Chase? Did you learn anything about comedic filmmaking from him?

[laughs] It was not a marriage made in heaven…

I was not very happy. It sort of inspired me to want to stay home and write. I couldn’t go on the set unless I knew I had in my hand a physical ticket to New York, so that I could just go at any time. I had to hold it in my hand so I knew that I had a way out.

What advice would you give to women trying to break into the industry?

I’m always asked that, but I feel like it’s so entirely different than it was. There’s a million little films, things on YouTube, and everybody’s got something going on. I had to work my ass off to get the money to get my little film out of the lab. I only had one copy of it, and I had to wait months for somebody to see it and get the copy back. Now you just make stuff, you email to people — but how do you grab their attention? It’s a different ballgame. Everybody has cameras, everybody is doing everything, so how do you make yourself stand out in that huge crowd? There wasn’t that huge crowd when I was starting, but it was so much harder. Now, it’s easier to do it, but how do you stand out? My experience is almost the polar opposite of what young people have to deal with now.

Amy Heckerling
Amy Heckerling

Do you have any advice for how to tune out all the bad stuff when you’re facing obstacles or having a creative lull? We see a lot of women making one great movie and then maybe one that doesn’t perform so well at the box office, and then we never hear about them again. You’re sort of a unicorn. What do you do to get through those tough times?

These are tough times right now. I got up and was doing these things that were streaming [referring to Amazon’s Red Oaks], and I was so depressed. I would say to my kid, “I can’t believe I have to get up at five o’clock to do something I can’t even tell you, ‘Oh you can see it on TV.’ You go to this site to see it, and it’s streaming. And she goes, ‘Ma, that’s all I ever watch.'” [laughs] You go where it is. Also, in a much more old-school way, I’m working with a young female director [Kristin Hanggi] on turning Clueless into a Broadway show. In that case I’m the writer, and she’s the director. Broadway’s a whole new bag for me. I find it interesting to learn new things and throw myself into something that’s scary. That’s fun.

Can you give us any updates on Clueless the musical?

We had a great reading. We’ll be workshopping it. We’ve got great producers [Dodger Theatricals, the team behind Jersey Boys and Into the Woods]. How people are singing and acting… that’s a thrill for me. That was so awesome.