On a Saturday afternoon in late September, the 62-year-old filmmaker Amy Heckerling stands in the atrium of the Georgia Aquarium, the largest in the Western Hemisphere, and watches it hum with chaotic activity. Strollers jockey in all directions like bumper cars; bored teens take selfies while waiting in line for the dolphin show; parents follow their children into the gift shop. Clad in sneakers, a hoodie, and a bucket hat out of which she cut a large hole so that her punk-rock rat’s-nest coif can spill out the top, Heckerling takes in the scene with a combination of awe and skepticism. “It’s kind of like a mall,” she says.

She would know. Heckerling is the director of two of the most iconic American teen movies of all time, Fast Times at Ridgemont High and, more than a decade later, Clueless. She is also, according to Box Office Mojo, the seventh-highest-grossing female filmmaker of all time, listed at a lifetime gross of $384 million (not adjusted for inflation); a good chunk of that change comes from the 1989 mega-hit Look Who’s Talking, which she wrote and directed. No one at the aquarium will recognize her, but it’s hard to imagine there are many adults among us who can’t quote a line from at least one of her films, be it Jeff Spicoli’s mantra, “Hey, bud, let’s party!,” or Cher Horowitz’s eternal “As if!”

Heckerling is in town for a Fast Times retrospective screening at the Savannah College of Art and Design’s Atlanta campus, where, the night prior, she gave a Q&A after the film. She is a bit perplexed by the recent interest in her earlier work; earlier in 2016, the arty New York theater Metrograph ran the first career-spanning series of Heckerling’s films, and a similar event in Grand Rapids, Michigan, shortly followed. “That was not like, ‘Oh boy, we have such expensive landscapes,’” she says of seeing Fast Times on the big screen. Still, Heckerling is always game to tell her side of her career’s story with characteristic candor. When she was asked to give the SCAD film students in attendance some advice, she told them, “It’s harder now, I think. Because they’re just gonna make a few superhero [movies], and then some people with low-budget money will make, you know, a couple of hundred low-budget movies that 90 percent of people won’t see. How do you get to be the one that made the movie that they all saw? It’s such a crapshoot.” When the perky moderator asked her to leave things on a more optimistic note, Heckerling crooked her arm and added in a sarcastic tone, “… but you can do it anyway!”

Heckerling’s demeanor is one of quick-witted pessimism: Debbie Downer if she had been a Borscht Belt comedian. We are standing in front of a glowing tank of potato grouper. “Look, they even suggest what the side dish should be!” she quips. Heckerling takes a picture of the fish and sends it to her 80-year-old mother with the caption, “Looks just like grandpa.” (Her mother will later respond with a confused-face emoji.) Onstage the night before, she described the making of Fast Times, her directorial debut, not only as one of Hollywood’s sole female directors at the time but also at the uncommonly young age of 27. She shot the movie for a major studio, Universal, but the executives seldom visited the set because a much more expensive production, The Best Little Whorehouse in Texas, was shooting on the same lot. She quickly realized this was a boon. “All the executives were very busy with that, and they left me alone, they forgot I was there,” she laughs in her thick Bronx accent. “That is the best! If you’re small and they don’t see ya, that’s a good thing.”

Or it is to a point. Though Heckerling has enjoyed a long, lucrative, and influential career, she’s not nearly as much of a household name as her fellow teen-flick patron saints Cameron Crowe and John Hughes, or her few female peers like Nancy Meyers and Nora Ephron. This partly has to do with the tumultuous second half of her career, which included box office failures, disastrous production deals, and more or less a decade and a half languishing in what she calls “director jail” — a series of events that has caused great difficulty getting new films made. But it is also not in her personality to indulge in the high Hollywood art of schmoozing. “Amy is not keen on selling. She will not sell herself,” her longtime agent, Ken Stovitz, tells me. “She’s not trying to please the studio executive like, ‘Oh yeah, oh my God, she was so amazing.’ That’s just not who she is.”

Or, as Heckerling puts it, she doesn’t like “making atta-boy sandwiches.” It’s a term she got from her brother. “He’s like, ‘Oh what, do they need some atta boys? Make ’em an atta-boy sandwich.’ To him, to compliment anybody on anything, it’s like you’re being a phony schmuck.”

Back at the aquarium, we exit past the gift shop. When we settle into her hotel lobby, Heckerling — who has an encyclopedic knowledge of film history — tells me the story of the Jewish cinematographer Karl Freund. When he was living in Berlin in the 1920s, Freund shot two of the most visually iconic German films of all time, F.W. Murnau’s The Last Laugh and Fritz Lang’s Metropolis. He then fled to the United States at the end of the decade, and he spent the final years of his career shooting I Love Lucy, among other projects, for which he designed an innovative lighting setup that some sitcoms still use to this day. Heckerling wonders, though, if someone as entrenched in the glamour of early film as Freund ever could have been satisfied working in the emerging medium of TV. “Who knows how he was feeling,” she says. “But I look at IMDb and see what people started doing and where they ended, and you go, well, it’s a different game. And that’s how it’s happening now.” In recent years, and especially since her time in “director jail,” Heckerling, too, has found herself working in TV, directing episodes of the Amazon coming-of-age show Red Oaks. She’s trying to keep an open mind about the ways the industry is shifting. “I’ll go to my kid like, ‘Oh, I gotta go [shoot] this thing that’s just streaming.’ She goes, ‘It’s all I watch.’”

“I don’t know,” she says, speaking as much of herself as Freund. “You gotta, like, bob and weave and figure it out.”

In January, San Diego State University’s Center for the Study of Women in Television & Film published its annual “Celluloid Ceiling” report on female filmmakers, and as usual the findings were deeply depressing. Women directed just 7 percent of the top 250 grossing films in America in 2016 — and that number is down two percentage points from 2015. Over the past two decades, these numbers have not budged; in fact, 2016’s numbers are also two points below the statistics from 1998, the first year its author, Martha Lauzen, released the report. The study also showed the trickle-down effect that hiring female directors has on women being hired for other production positions. “On films with female directors,” The Hollywood Reporter noted, “women comprised 64 percent of writers. On films with exclusively male directors, women accounted for just 9 percent of writers.”

The situation is just as bleak when you look at who is receiving the industry’s most prestigious honors. No women are nominated for the Best Director Oscar this year, which is the 85th time in 89 years that the category has been all male. A woman has won the Best Director Oscar only once (Kathryn Bigelow, for The Hurt Locker, in the ceremony’s 82nd year), and only three other women (Lina Wertmüller, Jane Campion, and Sofia Coppola) have ever even been nominated. No women of color have ever been nominated for a directing Oscar (a fact made more apparent by Ava DuVernay’s notable snub for Selma in 2015), and America’s first commercially distributed feature film directed by a black woman, Julie Dash’s Daughters of the Dust, did not come out until 1991, nearly a century after the birth of the film industry. Even though critics, scholars, and filmmakers alike have been having this conversation for decades, little has changed. In Hollywood, which takes every chance it can get to congratulate itself on its liberal progressivism, these numbers are damning to say the least.

Why don’t more women direct Hollywood films? It’s a question Heckerling has been asked ad nauseam in almost every interview she’s ever done, and she’s been sick of talking about it since at least 1982. “I did [Fast Times],” she recalled onstage at SCAD, “and all anybody asked me was, ‘What’s it like to be a female director?’ And I’m like, ‘I don’t knowwwww.’” She drawls the word out with disgust. “You were treated like some weird thing.”

Still, when Heckerling first decided she wanted to be a director, back when she was a teenager in the early ’70s, she didn’t have any female role models in her chosen field. “When I wanted to be a director, my father said, ‘Show me The New York Times and show me the want ads for woman directors,’” she tells me on the phone a few weeks after her trip to Atlanta. “Not the way most people in the arts find their jobs, but he was right, because there were very few actually working then. There was, what, Elaine May? That was it. So you couldn’t look to other women and say, ‘Yeah, they’re doing it.’”

May, though, is an especially precarious example: When the brilliant and groundbreaking former comedy partner of Mike Nichols started directing her own movies in the early ’70s, like the dark comedy The Heartbreak Kid and the gangster-buddy picture Mikey and Nicky, she quickly gained a reputation in Hollywood for shooting excessive amounts of film, acting indecisively on set, and, as a natural consequence, going catastrophically over budget. As the sole woman directing studio films in Hollywood at that time, May had to bear a rather impossible burden: The success or failure of all future female directors was on her shoulders. Her failures were seen not as her own, but the failures of the Female Director.

May’s status as box office poison was chiseled in stone in 1987, when she directed Ishtar, one of the most notorious flops in the history of Hollywood. (The film was so universally maligned that it spawned a famous Far Side comic captioned “Hell’s video store,” in which the shelves are lined with nothing but copies of Ishtar on VHS.) In the decades since, May has continued to write screenplays and work in Hollywood as a script doctor, but she’s never directed another movie.

This and other cautionary tales have hovered over Heckerling throughout her career, she says, and in some sense it’s influenced almost every professional choice she’s made. She’s observed the same arc occurring over and over again with her female peers, like Claudia Weill (whose best-known movie is the 1978 female-driven cult classic Girlfriends) and Martha Coolidge (the director of the ’80s indie Valley Girl, which starred a young Nicolas Cage). But to Heckerling the greatest tragedy of Hollywood sexism is the career of her friend Joan Micklin Silver, a director who independently financed her debut feature, the 1975 immigrant drama Hester Street. “[That] is one of the best movies made by women. And one of the best movies about the immigrant situation. After Hester Street, people should have been knocking themselves over to give her the next movie and a big step up to a bigger budget and big stars and whatever.” Instead, Micklin Silver made smaller independent movies like Between the Lines and an Ann Beattie adaptation, Chilly Scenes of Winter, neither of which made much of a splash, both of which now have some cult admirers but are rarely seen because they’re so difficult to track down. Her name, more often than not, evokes blank stares. “Why isn’t that like, oh, here’s the female Scorsese?” Heckerling asks. “Why does nobody know about that? ARGH!”

“A guy gets chances,” she says. But a female director? “It’s like, you fuck up [once] and that’s it, goodbye.”

Once, shortly before she got her big break making Fast Times, someone told Heckerling the unspoken golden rule of being a director: If your movie grosses three times what it cost, you get to make another one. “So I thought, ‘Oh please God, let this make $18 million,’” she told the crowd at SCAD. “Please, God, let me do it again. That’s all I want to do in my life.”

The audience this night is mixed: about half Gen-Xers lovingly reciting every one of Spicoli’s lines (“That was my skull! I’m so wasted!”), and half 20-somethings whose parents probably hadn’t even met when the film first came out — these are the Clueless fans. Despite its lack of stunning landscapes, it’s clear from the energy in the room that Fast Times has held up better than almost all the other teen sex comedies of the ’80s. It is the rare movie of the Porky’s era that treats teens — and even more rarely, teen girls — as real, complex human beings.

Which is the reason Universal almost canned Fast Times before it made it to theaters. “They showed it at a screening in Orange County,” Heckerling recalls, “which is a very, very conservative neighborhood in California. And we got really nasty comments like, ‘How dare you show us teenagers only doing sex!,’ and, ‘How dare you show an abortion! We don’t believe in that!’” She sighs, tugging an invisible collar. “I’m like, ‘Ooh boy, I’m in trouble.’”

Initially, the studio sided with Orange County: Fast Times got a limited release — until people at Universal saw what was happening in the few theaters where it was playing. One day, a friend called Heckerling and told her to go see the movie in a theater. “So I went, and people were saying the dialogue with it. And I was like, ‘Oh my God!’ They came, and they must have seen it and come again, because they know it! That was one of those moments in your life, you have maybe five of them. I had a baby, people said the dialogue of Fast Times …”

It wasn’t a smash hit at the box office, but it cleared the all-important bar: It made more than three times its budget. And so she got to make another one.

But not another one just like it, the result of a conscious decision to avoid being pigeon-holed as a teen-movie director. Her next project was a hard pivot: 1984’s Johnny Dangerously, a goofy satire of early gangster movies starring Michael Keaton and Joe Piscopo. (Because it’s his favorite Heckerling movie, Metrograph programmer Jake Perlin was disappointed that its screening at the theater attracted only a modest crowd. One man, though, had been laughing uproariously at every joke, and on the way out Perlin realized it was Wallace Shawn.) Heckerling had fun filming Johnny, but panic began to set in when she considered what to do next.

“Johnny Dangerously had had a [test] screening where the numbers weren’t good,” she says. “And if I had a movie coming out and I was a female and it didn’t do well, that would be the end of me. So that was really the reason I did [National Lampoon’s] European Vacation, which is not my favorite film in the world. And certainly I was extremely miserable working on it, but I figured they would market it and put money into it to try and make it do well. And I’d be working on it before Johnny Dangerously came out, so it would take them longer to write me off. I would be a question mark for a little while.”

It worked, ostensibly: European Vacation was the 14th-highest-domestic-grossing film of 1985, making almost $50 million. But when Heckerling talks about this period of her life now, she seems exhausted by her youthful ambition and her frenzy to stay one step ahead of failure. “I had a million benchmarks,” she sighs. “I was driving myself crazy. … They were also saying all this stuff about [women],” she says, referring to a deeply misleading and since-debunked 1986 Newsweek story that claimed a woman was “more likely to be killed by a terrorist than to find a husband over 40.”

“I wanted to do three movies before I had a baby,” Heckerling says. “I wanted to have a baby by the time I was 30. Which meant, like, being married or whatever. I wanted to beat all those deadlines they were imposing.”

She more or less cleared those hurdles: Heckerling married the writer-director Neal Israel in 1984 (it was her second marriage; they later divorced), had a daughter, Mollie, in 1985, and directed European Vacation, her third feature, which came out just a few months after her 31st birthday. The birth of her daughter was a creative turning point. People tend to talk about pregnancy as something that stalls a woman’s career, but in Heckerling’s case, it inspired the biggest and most lucrative success of her career.

Heckerling wrote Look Who’s Talking during a period when she decided she was through directing other people’s scripts; she’d achieved all her exhausting, culturally sanctioned “benchmarks,” and now she was ready to play the Hollywood game on her own terms. She came up with the idea while she and Israel, as new parents, would amuse themselves by doing voices as their silent newborn.

“She handwrote her scripts,” says Twink Caplan, Heckerling’s friend and collaborator, who played the wisecracking sidekick in Talking and, most famously, Clueless’s lipstick-toothed history teacher Miss Geist. “As soon as I’d get her pages, I’d type them up. It was such an honor because I loved everything she wrote. I typed so fast and as I was typing, my mouth [was] open ’cause I’m thinking, ‘Oh my God, that is so funny.’”

The movie is, of course, famously silly, but there are some surprisingly modern gender politics at the heart of the film’s romantic relationship, between Mollie and James, played by a post-slump, pre–Pulp Fiction John Travolta. She’s the breadwinner, and much of the film’s conflict is her own internal struggle to accept the love of a man who is not her household’s provider — to accept her own professional success and power, even if it overshadows her partner’s. It’s hard to imagine a man writing this character exactly as Heckerling did.

“It cost very little,” Heckerling says of the production, which took place when TriStar was up for sale. But when Sony bought the smaller studio, even though Look Who’s Talking was scoring high in test screenings, the new executives decided to shelf it. “Their excuse was that John Travolta was box office poison,” Heckerling says, still in disbelief. “Now, he may have been in a down period. But the guy made Grease and Saturday Night Fever, and still was as cute as ever.” According to Heckerling, it took the threat of a lawsuit from Travolta and costar Bruce Willis (who voices Baby Mikey) to spur Columbia into action. “I can’t say that all the good things that happened to me were because of other women,” Heckerling says. Especially because in this case, “John Travolta and Bruce Willis, men, saved my ass.”

Look Who’s Talking was a smash. Heckerling didn’t just clear the bar of the golden rule, she obliterated it: The first film she’d both written and directed — and her most woman-centric film yet — grossed an astonishing $297 million worldwide on a $7.5 million budget.

And yet what should have been a moment of celebration for Heckerling turned out to be one of the lower moments of her career. In the midst of the film’s success, two women filed a $20 million lawsuit against TriStar alleging that Heckerling had plagiarized their student film about a talking baby. The studio eventually settled, and Heckerling is still legally barred from talking about the suit, but she still recalls the year-and-a-half-long legal battle as a time of deep emotional exhaustion. “I was very bummed out,” she says. “When I should have finally had a moment of feeling good, it immediately turned to crap.”

The moderator at the SCAD retrospective, a cheerful blonde in her late 20s, was there to ask questions about Clueless. It was abundantly clear. As soon as she’d finished her questions about Fast Times, she said with an excitement she could barely contain, “I know, myself included, there are a lot of Clueless fans in the audience … ”

This kind of adulation is neither surprising nor rare. Though it isn’t the highest grossing of Heckerling’s films, Clueless has gone on to become the most beloved. With its exquisitely styled plaid and endlessly quotable vernacular, Clueless is one of the quintessential texts of ’90s nostalgia. It spawned a spinoff TV show, rocketed several of its up-and-coming players (Alicia Silverstone, Brittany Murphy, Paul Rudd) into stardom, and kicked off a trend of high-school-classic literature movies (10 Things I Hate About You, Cruel Intentions, Romeo + Juliet). Its influence continues to ripple today: In 2014, Iggy Azalea and Charli XCX paid detailed homage to the film and its fashion in the video for their monster hit “Fancy.” A year prior, the clothing label Wildfox put out a Clueless-inspired spring line called “The Kids in America.”

Clueless was a respite for Heckerling, who’d spent a few creatively unfulfilling years caught in the fallout of the legal mess surrounding Look Who’s Talking. The studio agreed to foot the bill for the lawsuit if she’d agree to write and direct a sequel — quickly. “So there I am doing this sequel,” she says of Look Who’s Talking Too, “when I’ve already thought, ‘It’s over. It’s done. The baby said something.’” She also worked with Columbia on Baby Talk, an ABC sitcom loosely based on Look Who’s Talking, which ran from 1991 to 1992 and costarred a young, lion-maned George Clooney. She had written another script that had gone into development at Disney — before it dropped the project for being “too smart.” “And so I said, all right, you want dumb?” Heckerling says. “I’ll show you dumb … ”

Heckerling is being a little facetious here. Clueless is a cinematic sleight-of-hand: It’s an excessively smart movie about “dumb” people. Or, more subversively, it’s a sly assertion that the types of people that can be easily dismissed as “ditzes” or “airheads” — usually teenage girls — often possess an intelligence the world doesn’t give them credit for. Cher might mispronounce the word “Haitians” (a real gaffe by Silverstone that Heckerling left in), but as her love interest Josh gets to know her better, he realizes there’s more substance to her than he ever would have thought. Clueless holds up and probably always will thanks to Heckerling’s razor-sharp script, which is loosely based on Jane Austen’s Emma. Part of Clueless’s brilliance comes from the fact that it is a glorious culture clash of the high-brow and low, from the “Rollin’ With the Homies” dance to the sheer perfection of Paul Rudd’s goateed Josh reading Nietzsche by the pool.

In the earliest stages of development, though, Clueless was just as touch-and-go as Fast Times — until star producer Scott Rudin attached his name to it and the script found a welcome home at Paramount. “Now, you’ll run into 900 ex–studio executives who say, ‘Oh, yeah, I really wanted to make Clueless,’” says Stovitz. “They all had a chance to make it — everybody passed on it two or three times.”

Once the production finally got going, though, Clueless was the best experience of Heckerling’s career. “I was happiest on Clueless,” she recalls. “That was the closest something in my head came to what was on the screen. I liked everybody in it, there was no aggravation, the studio left me alone and was supportive of selling it. It was just a great experience.”

Heckerling self-identifies as a Tai (the earnest skater girl whom the heroine makes over, played brilliantly by the late Brittany Murphy), not a Cher. In fact, the creation of the most famous character she’s ever written was something of a thought experiment, an attempt at embodying a certain kind of optimism that doesn’t come easy to her. “I remember reading Emma. I remember reading Gentlemen Prefer Blondes,” she said in a recent, book-length oral history of Clueless. “Those characters: what I gravitated to was how positive they could be.”

“I’m happiest when I’m in that sort of fantasyland. 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.”

Amy Heckerling was born on May 7, 1954, in a Jewish neighborhood in the Bronx. Many of her neighbors and the other tenants in her building were Holocaust survivors. Her mother kept old European newspapers covered in plastic: “Here’s the day when they started wearing the gold stars, here’s when they couldn’t walk the streets.” Heckerling recalls going with her parents to the butcher, the baker, the pickle guy, and seeing them pull up their sleeves to show Amy and her young siblings their numbered tattoos. When asked what effect these experiences had on her, she says, “I guess it teaches you that the world is not a place that particularly likes you.”

Heckerling’s parents both worked as accountants (much like Kirstie Alley’s Mollie in Look Who’s Talking; Heckerling cast her own father as the character’s dad), so she became a latchkey kid, raised by episodes of Gidget and old classic movies that aired on TV. She learned to escape into the optimistic fantasyland of comedy; she also developed a lifelong obsession with James Cagney. Like several other filmmakers of her generation, she says she learned how to be a director from Million Dollar Movie, which aired on a local New York station. “That was life-changing,” she recalls. “[They] would show you the same movies every night, so you could study it. You could see, you know, Yankee Doodle Dandy seven times a week. Or King Kong, or Jolson Sings Again. And you start to know what the whole script is, unconsciously.”

One day, when Heckerling was 14, a teacher asked all the students in her class to write down what they wanted to do with their lives. Heckerling’s greatest aspiration at that point was to be a writer for Mad Magazine, so she wrote that down, but she became incensed when the boy next to her wrote that he wanted to be a movie director. “I just got insanely jealous,” she said in the book Is That a Gun in Your Pocket: Women’s Experience of Power in Hollywood, by Rachel Abramowitz, “I just thought, ‘You said you can make movies. I love them more than you do. And besides, you cheat off me on your tests, so I’m smarter, so I should do it.’”

She set out on her dream of attending film school with fiery determination. She worked three jobs and applied to NYU film school; her work there (which she mostly describes as “bizarre” musicals) got her into the American Film Institute’s prestigious directing program. She found the program a bit snobby and elitist, and she found it difficult to adjust to L.A.’s sunny optimism. Still, she thrived in school and made important connections; she dated and began a lifelong friendship with her classmate Martin Brest, who would go on to make Beverly Hills Cop and Midnight Run. Heckerling’s thesis film, completed in 1977, was called Getting It Over With, a rather radical display of subjective female sexuality for the time; it’s about a girl trying to lose her virginity before her 20th birthday.

Her 28-minute short got some buzz around town. One studio liked it so much that they paid her to write a feature-length script, and Heckerling’s idea was to focus it on a long-term friendship between two women who fall in love with the same man. When it was complete she spent her days lolling around in her apartment, waiting for someone important to read it. Then one day, Mark Rosenberg, a producer at Warner Bros., asked her to lunch. Heckerling was ecstatic, until she sat down across from Rosenberg and realized he just wanted to ask her about her boyfriend. “And so I was telling him how great Marty [Brest] was,” she recalls, “and I finally get around to saying, ‘So, um … what about my script?’ And he was like, ‘Oh, I didn’t read it yet, I’ll read it. But you know, it’s about two women who stay friends for all these years and … women don’t stay friends.’”

She shakes her head, recounting this decades later. “What do you say to that? When you’re in your 20s, you can’t say, ‘I’ve liked the same person since high school,’ because that doesn’t mean anything yet.”

This was perhaps Heckerling’s first major taste of Hollywood disillusionment — but far from her last. The movie never got made.

A rebuttal to that producer, decades later: Amy Heckerling and Alicia Silverstone stayed friends. They are actually meeting up for dinner shortly after our hotel lobby chat, because Silverstone just happens to be in Atlanta. “There really is no other Alicia,” Heckerling gushes; the two worked together again on both Vamps and Suburgatory, though Silverstone skipped the TV spinoff of Clueless. Heckerling struggled with the nature of prime-time broadcast TV — having both a network and a studio breathing down her back and asking her to change or censor lines of dialogue. “Even if you feel like you wrote something great, then right before you start [shooting] the network will call and say, ‘We don’t think that they should do this or that yet, maybe they should only blah blah,’ and then you go, well then there’s no point to that episode. So, I wasn’t happy.” Clueless aired on ABC for one season, and then, after Heckerling became less involved, it moved to UPN for two.

“She was offered every studio movie in the world,” Stovitz says, “and [she] turned them all down because she’s not interested in doing what would be the obvious Clueless follow-up. She was interested in doing her own thing.” She signed on as a coproducer of A Night at the Roxbury; Heckerling was rumored to have stepped in to ghost-direct at least a few scenes. All the while, the clock was ticking on a follow-up to her latest success. At the time, her post-Clueless choosiness might have seemed like a declaration of independence, but in hindsight it looks more like a squandering of momentum.

Heckerling didn’t put out another film until 2000, the bleeding-heart college-coming-of-age flick (a.k.a. that movie where Jason Biggs wears a floppy hat) Loser. The film is a bit of a mess: Biggs’s small-town nice guy character is a little too saintly to be sympathetic, and there’s a well-intentioned but ultimately didactic subplot about the prevalence of date-rape drugs. It was both a critical and commercial failure, making only $15.6 million at the domestic box office and earning a measly 24 percent on Rotten Tomatoes.

“That movie was ruined in post,” Stovitz says. “Loser was really good until the studio said, ‘No, you’ve got to make it PG-13 rather than R,’ and it ruined the movie. Just ruined the movie.” The head of the studio reportedly brought Heckerling their marketing department’s research that PG-13 comedies performed better than R-rated comedies. “Of course, now only R-rated comedies work,” Stovitz sighs.

“Oh, I don’t like to even think about that one anymore,” Heckerling tells me. “It certainly didn’t do me any good. [But] I look at the careers of a lot of men who have had much, much, much bigger flops than that and did not get treated the same.”

When I ask her to elaborate on her treatment in the industry after Loser, though, she characteristically deflects to humor. “Well I had to wear this giant dunce hat,” she says. “But I look good in hats!”

The tale of Loser, though, is downright rosy compared to Heckerling’s next film, I Could Never Be Your Woman, an acerbic romantic comedy starring Michelle Pfeiffer, Paul Rudd, and (in her first major film role) a precocious Saoirse Ronan. In some ways, it’s Heckerling’s most baldly autobiographical film: Pfeiffer plays a middle-aged TV producer working on a ridiculous sitcom about teens (based on Heckerling’s experiences briefly working on the Clueless TV show) who must battle both double standards and inner ageist demons when she falls for a younger man. Paramount initially bought the script, but shelved it not long after. “There was some concern about doing a movie with an older female protagonist — not everybody’s favorite demographic,” Heckerling told Entertainment Weekly in 2008.

Stovitz agrees. “People weren’t making films about women in crisis over their age,” he says. “That wasn’t, ‘Oh my God, I can’t wait to put our money into that.’ And that really was it. It didn’t matter what was on the page. Studios weren’t interested in that topic.”

Desperate to get her script into production (Pfeiffer and Rudd were already attached to the project), Heckerling put her faith in an up-and-coming indie production company called Bauer Martinez Entertainment, headed by a flamboyant, cigar-chomping 39-year-old Frenchman named Philippe Martinez. (Martinez could not be reached for comment.) Martinez was new in town and eager to put his name on the map in Hollywood — and to start writing checks. He funded Woman’s $25 million budget, and the film began shooting in August 2005. There were some early red flags, though, like Martinez’s desire to shoot the film in London to qualify for U.K. tax breaks, which also meant, according to Heckerling’s commentary track on the DVD, that more than half of the actors of this L.A. satire had to be British.

“He was all over it, like, ‘I love it! It’s perfect! Let’s go!’” Stovitz recalls. “Then, of course, he turned out to not be as advertised.”

The truth eventually came out about Martinez: The real reason he’d come to Hollywood was that he’d been convicted of fraud in France, on charges related to a failed production company, and had spent six months in jail. It was no great surprise that he bungled the Woman’s financing and distribution deal; far from fulfilling Martinez’s promises of glory, according to Variety the company suffered several rounds of layoffs throughout Woman’s production. After a long, tortuous saga that involved a pay cut for Pfeiffer and MGM (which had signed on to distribute the film) severing its ties with Martinez, the finished film sat on the shelf for more than two years, before it went straight to DVD in February 2008. When it finally came out, critics were savage. “A desperately unfunny mix of tepid showbiz satire and formulaic romantic comedy,” wrote Variety, “writer-director Amy Heckerling’s long-delayed, trouble-plagued I Could Never Be Your Woman has finally been released — or more precisely unleashed — as a direct to video title.”

Heckerling doesn’t like to dwell too much on this part of the story. When I ask if she has any regrets from the later part of her career, she brushes the question off. “That’s so easy to do, because you go, ‘Oh I should have done this or I could have done that.’ But you don’t know. You could say, ‘Why didn’t I do this movie?’ Then you go, ‘I would have been in England [driving] on the wrong side and I would have been in a car accident and died,’” she laughs.

But this is the moment in Heckerling’s career when her somewhat traditional commitment to that old ideal of the Big Studio Film — as opposed to the low-budget indie — may have hindered her. Smart, subversive themes and an offbeat humor run throughout each of her films, and these are just the sort of idiosyncrasies that studios — particularly in the 21st century — like to iron out of anything that costs more than $10 million or $20 million. But ironically, the production debacle of I Could Never Be Your Woman scared her off from going further into the realm of independent film. “If this is independence, I’d rather go back to what they call ‘the devil you know,’” she told the A.V. Club in 2008, soured by her experience with Martinez. “It was crazy,” Stovitz says. “Look at the cast of the movie. The cast is incredible. It got made for all the wrong reasons, [but] it should’ve gotten made for all the right reasons because it really was a great idea.”

The tragedy of I Could Never Be Your Woman is not the fact that it went straight to DVD, but the fact that Hollywood was so averse to putting money into a comedy about a woman over 40 — a woman written and directed by a proven female filmmaker, and played by someone as conventionally gorgeous as Michelle Pfeiffer — that Heckerling had to turn to someone like Martinez just to get it made.

Female directors have and will continue to set foot in uncharted territory — how can they not, when so much of it is uncharted? — and every so often a triumphant milestone makes the news. Frozen made codirector Jennifer Lee both the first woman to helm a Walt Disney Animation Studios movie and the first woman to direct a film that earned over $1 billion in gross box office revenue. When Ava DuVernay signed on last spring to direct the forthcoming blockbuster A Wrinkle in Time, she became the first woman of color to direct a live-action movie with a budget over $100 million. With this summer’s Wonder Woman, Patty Jenkins will be the first woman to direct a DC Comics movie. These are monumental achievements, but they are underscored by the immense pressure on these films to succeed, to stand for something larger than themselves; an unfair truth of the industry is that the opportunities for all women to direct superhero films in the future will be determined by how much money Jenkins’s Wonder Woman makes. The Female Director in the 21st century has cleared so many bars, but she has not yet achieved a milestone that’s less glamorous but no less important to both creativity and equality: the right to fail.

“Let me just help my mom down the stairs. Hold on one second,” Heckerling tells me over the phone one afternoon in December. She moved back to New York a few years ago, when Mollie had a daughter of her own. It’s not unusual for four generations of the women in Heckerling’s family to all be hanging out together, like they are today, but Heckerling has noted that their preferred methods of leisure-time media intake differs. Mollie, who’s 31, likes to stream TV shows from home. “It’s much easier to get my mother to go to a movie,” Heckerling jokes. “I have to put the walker in a cab, but other than that!”

Mollie Israel shares her mother’s sense of humor as well as her interest in filmmaking. A fixture on her mother’s set since she was an infant, Mollie recalls one of her earliest production memories: “I was crying and Mom passed me off to my grandma, and when they called that they were rolling I just stopped crying and said, ‘Shh! Quiet on the set! We’re rolling!’”

“She used to stop crying until she heard cut,” her mother proudly adds.

Mollie recently completed her first screenplay and has been shopping it around with several producers. She’s not terribly worried if this first script doesn’t get produced, though, because she’s got plenty of other projects on her plate, including an “adult puppet show” she’s been working on with some friends, which she describes as “Meet the Feebles meets The Honeymooners.” Though she’s interested in film, Mollie is more of a creative polyglot than her mom, a shift Heckerling sees as generational. “She’s doing stand-up now,” she tells me, a little wistfully. “She was in a rock group. She’s all over the place. And it’s weird … kids seem to do a lot more different things [now]. I was focused on this one thing.”

For most of her career, though, Heckerling has had one foot in the TV world, and she’s adapted to the streaming era by directing a few episodes of Amazon’s coming-of-age series Red Oaks. She’s also working on developing a Clueless musical, though the pace of getting a Broadway show into production is — much to her frustration — an even slower slog than getting a Hollywood film made. But, as ever, she still writes compulsively, and she’s working on something that is clearly important to her, because she refuses to give me any details about it. “You know, I’m very superstitious,” she laughs. “So I feel like if I mention stuff, then it will be jinxed.”

When I ask Mollie what she learned about directing from being on her mom’s sets, she tells me, “She always knows what she wants and she always talks to everyone with respect. The crew loves her. To me it’s just, you show up, you do as good a job as you can, and you try to work on things that your heart is really in. You’ll see a lot of people that just work on the same old crap and they don’t really seem happy or they land a big deal and they treat everyone like garbage and then they blow it all. The one thing my mom’s taught me in everything is that slow and steady wins the race. You just keep doing it.”

When I ask Heckerling what advice she’d give to her daughter, her answer is much less sentimental. “Try not to be too much like me,” she laughs.

Right after film school, back when she was waiting for her ship to come in, Amy Heckerling got a job on the Warner Bros. lot. The studio was developing a spoof on the MGM musical compilation That’s Entertainment! — but with talking animals. Heckerling’s job was syncing up prerecorded voice-overs with animal footage. “The hardest part of this job was the Flipper stuff,” she recalled in the book Breaking In: How 20 Film Directors Got Their Start, by Nicholas Jarecki. “Because Flipper only made one sound: ‘Aahhh.’”

Back near the edit rooms she remembers seeing rows and rows of these mysterious, oddly foreboding steel lockers. One day she asked a coworker, “What the hell is that?” They replied, “That’s where the nitrate stuff is stored.”

“And I go, ‘Oh, that could’ve blown up at any time,’” Heckerling laughs. “There’s a big photography company in Rochester, New York, that is a cancer-causing — I think it was non-Hodgkin’s lymphoma. … So in that respect: Expensive, poisonous, explosive, but you know, it looks good.”

Bleakly comical as ever, this is the story that Heckerling tells me when I ask if she’s nostalgic for the days of old Hollywood — James Cagney imprinted in silver nitrate, studio-hired directors barking orders from megaphones. This strikes me as a poignant but progressive way of thinking about the past, and all the power structures that implies: glamorous, sure, but toxic when taken to its literal extreme.

The sun is setting in downtown Atlanta; it’s time for Heckerling to go meet Silverstone for dinner. “You go, ‘OK, it’s a different world,’” Heckerling says. “Do I feel bad that such a small percentage of women are making studio movies? Sure. Does anybody care about studio movies anymore?”

She lets the question hang in the air.

“I love [studio movies], but I kind of feel like this is dinosaurs. And you know — as you saw from the aquarium — some species live and some don’t.”