Why isn’t the female director of Clueless a bigger Hollywood success story?

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Hannah-Rose Yee
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It’s one of the most iconic high school movies ever made. But why has its writer and director found it so hard to get more of her work made? 

If it were up to me, every woman would know the name Amy Heckerling.

This is the woman who gave us the clever social comedy and the talking babies of Look Who’s Talking. This is the woman who perfected the art of the high school movie, first with Fast Times at Ridgemont High in 1982 and then with the transcendent Clueless in 1995. 

This is the movie that launched the careers of Alicia Silverstone, Paul Rudd and the late Brittany Murphy. This is the movie whose aesthetic has proven so enduring, whose particular parlance has so totally infiltrated the wider zeitgeist. There are things we say because Heckerling wrote them in Clueless. “As if,” I can hear you say. Exactly.

As a filmmaker, she possesses that rare gift: a desire to show, not tell. She never talks down to her characters or belittles the things that they love, those slinky little Azzedine Alaia dresses, those neat little Jeep Wranglers. She loves them, even when they think that Billie Holiday is a man or that the author of Shakespeare’s Sonnet 18 is Cliff’s Notes. And she knows that in all of that silliness and embarrassment and relatability is the stuff of life. She knows that, because she’s lived it. 

Amy Heckerling

So why, when we talk about the great female directors, don’t we talk enough about Heckerling? Why, after making one of the best high school movies of all time and, in my opinion, one of the best Jane Austen adaptations of all time, did Heckerling struggle to get another movie made? Why were there five years between Clueless and the release of Loser, her next film? Why did her project after that, the Michelle Pfeiffer-starring I Could Never Be Your Woman release straight to video? And why, for the past six years, has Heckerling mostly worked as a director on television shows that aren’t her own, like The Carrie Diaries, Gossip Girl and Rake?

Speaking today to the New York Times, Heckerling reflects back on her career and the way in which she felt her success influenced by her gender.

“You know, I keep thinking, like, well, it’s my fault. If I was better, it wouldn’t have happened,” Heckerling told the New York Times. “I don’t go around going, boy, I’m so good, but I do see a lot of guys that I don’t think are that good and they get more chances or whatever, but I tend to think if I was better this [expletive] wouldn’t have happened to me.”

Clueless: Dionne Davenport (Stacey Dash), Tai (Brittany Murphy) and Cher Horowitz (Alicia Silverstone)

As if! 

After directing Fast Times at Ridgemont High, a huge success, Heckerling wanted to make a gangster movie she had written called Johnny Dangerously. But she felt anxious about its potential at the box office, especially in light of her recent success. “I thought, well, men can have a failure,” Heckerling told the New York Times. “Women can’t, and so I have to have something will make money, and it has to already be in the works so that they’ll discount Johnny Dangerously’s failure.”

That movie, the one she felt would “make money”, was National Lampoon’s European Vacation, a movie that Heckerling hates. “I despise that movie,” she said. “I just felt very like, I don’t know if I even want to ever do this again.”

All through her career, Heckerling has felt the crushing weight of this imposter syndrome. But for Heckerling it has been couched in the sexism baked into the infrastructure of Hollywood. 

According to the New York Times, small things would happen to Heckerling projects that meant that they were set up to fail from the start. There would be no money for a killer soundtrack. There would be no distribution deal. There would be movies released in only a tiny number of cinemas, which means only a tiny amount of money was made, which meant it was harder to get any further films financed by studio heads glued to the balance sheets. Heckerling’s missteps, like the Jason Biggs-starring Loser, were amplified and her successes (Clueless, Looks Who’s Talking, Fast Times, did we mention Clueless?) are forgotten. 

A young Sean Penn in Fast Times at Ridgemont High

Heckerling was working in an era before Time’s Up, before a woman won the Oscar for Best Director (Kathryn Bigelow, 2010), before a woman would direct a big budget, blockbuster superhero movie. She was making movies, and she was making the kinds of movies that men usually made, “slobby” comedies like National Lampoon and Fast Times. Plus she was making them well, and they made money. And yet it’s been almost a decade since her last solo project.

Today, Heckerling is working on the Broadway adaptation of Clueless, opening for previews next week. Like the musical adaptations of Pretty Woman and Legally Blonde, it has the potential to become a massive hit.

The time couldn’t be more ripe for a Heckerling resurgence. The institutionalised sexism of the film industry is finally starting to be dismantled. Mimi Leder, another female director and Heckerling’s contemporary in the eighties and nineties, is making her comeback this year with the Ruth Bader Ginsberg biopic On the Basis of Sex. This, after Leder was put in director jail when, after a series of hits, she made one flop (Pay It Forward) in 2000.

“The experience of going to Movie Jail was deafening and painful,” Leder told The Ringer last year. “But I remained in television. I didn’t stop working. I directed nine pilots, and six of them went to series. They’re not on the air anymore, but I didn’t stop working. I just stopped making films.” 

Mimi Leder

Like Heckerling, for the last decade Leder has been working steadily in television, directing some of the best episodes of The Leftovers and Shameless. Next year, she will direct every episode of Reese Witherspoon and Jennifer Aniston’s series about morning television for Apple’s original content network.

The cells of director jail are littered with the female filmmakers of Hollywood. “If a woman makes a mistake, people remember it,” Kimberly Pierce, the director of Boys Don’t Cry, put it to IndieWire. “If a man makes a mistake, more often than not, people forget it.” 

Leder organised a jailbreak and sprung herself from prison. We’re hoping that Heckerling is next.  

Images: Getty


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Hannah-Rose Yee

Hannah-Rose Yee is a writer based in London. You can find her on the internet talking about movies, television and Chris Pine.

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