‘Clueless’ Was Amy Heckerling’s Masterpiece. Is She Done With It? As If.

Amy Heckerling thought “Clueless” should be a musical, right from the beginning. “Even when we were shooting the movie,” she said, “it felt like, at any point, it should burst out in song.”

Back then, in 1994, people around her agreed that it had the heart of one. She would watch Alicia Silverstone and Paul Rudd as Cher and Josh, tiptoeing around each other as they fought and flirted, and wonder why they couldn’t just burst into song. “Two people falling in love, well, they got to sing,” she said. But the people who usually fund these ventures did not agree. A musical was considered too expensive, and not worth it. People wouldn’t see it, they told her and blah, blah, blah.

She’d always wanted to make a musical. She had in mind a black version of “Bye Bye Birdie,” with Richard Pryor, Prince and a very young Will Smith. “I was told you can have a black actor with a white actor, but you can’t have more than that.” So, no to that, too.

But she never stopped trying with “Clueless.” She never stops trying with anything, really, even when the parts of her that wonder if the world is trying to tell her something seem louder than her certainty that Cher Horowitz should live. In those moments, she looks inside herself and realizes she really can’t let “Clueless” go.

That’s perhaps why it was so gratifying to be sitting, on a Wednesday in November, on the ninth floor of the New 42nd Street Studios, watching a gaggle of sparkling young people rehearsing for the Off Broadway adaptation “Clueless, The Musical.” They were running through the scene in which Cher (Dove Cameron) and Tai (Ephie Aardema) have a confrontation that ends with Tai saying, “You’re a virgin who can’t drive,” and walking away defiantly while taking a call on a ’90s-era flip phone.

Aardema was a child when “Clueless” was in theaters and when flip phones the size of a shoe were a thing. She had to figure out how to walk off while remembering to open the phone. Who opens a phone? Old people is who. Then, when she finally remembered, she answered it upside down. O.K., O.K. Let’s take it from the top of “You’re a virgin who can’t drive.”

Heckerling, who is 64, wore jeans and a plaid shirt and wrote notes on a tiny Post-it. Her hair is like a fern: Sprouting up from her scalp in all directions, its leaves layering upon one another, but pitch black. She talks low and fast in her Bronx-then-Queens accent, so that she sounds like a gangster in one of her beloved James Cagney movies. She’s prone to saying “blah, blah, blah” when she talks about things that she’s uncomfortable with or that she thinks are obvious or when she just seems tired of hearing herself talk. She says “anyway” to end a thought, particularly when she thinks she’s already said too much or there’s just nothing to do about the thing she was talking about. With all this, her most indelible feature is the heavy black eyeliner she wears on both her upper and lower eyelids, and her resting expression, which is a weariness that sometimes breaks like the sun through clouds into a delighted smile.

In light of the success of “Clueless” as a movie, in light of the fact that it seemed that every film more than 10 years old was now being adapted into a Broadway show — and yes, in light of how much its creator still wanted to spend time with the material — Heckerling pursued a stage version. By the time of this rehearsal, Heckerling had been trying to mount this thing for years. It was first in workshops with Barry and Fran Weissler (“Chicago”), who told Heckerling they wanted her to be involved, she said, but then only invited her to readings. Their version of “Clueless” wasn’t exactly in line with her vision. Their team wanted the musical to start with the daily arrival of the hired help — housekeepers, gardeners, etc.— into Beverly Hills on city buses. The story of this privileged world would be seen through their eyes.

But “Clueless” isn’t a story about class. It’s a fantasy, written by someone who grew up without a lot of money in New York and who always wondered what life would be like in a place where things seemed easy, where it was always summer and a girl could be loved and accepted and keep a positive outlook. “That’s like, ‘What’s it like to live in a Fred Astaire movie?’” she said. “You don’t go, ‘There’s a Depression outside.’”

The Weisslers didn’t renew their option on “Clueless,” and Heckerling had been introduced to a producer from the Dodgers, the producers behind hits like “Jersey Boys” and “Matilda the Musical,” who would help get this iteration of “Clueless” off the ground. They attached Kristin Hanggi and Kelly Devine, the director and choreographer team behind hits like “Rock of Ages.” Scott Elliott, the founding artistic director of New Group, had been at a few table reads and had kept an eye on the production. Eventually, “Clueless, The Musical” had a home.

They hired their Cher: Cameron, who starred in “Liv and Maddie” and “Descendants” and who looks like an anime drawing under 72 Instagram filters. They cast their Josh, their Dionne, their Murray. Slowly, as Heckerling watched younger movies become musical hits (like “Mean Girls”), “Clueless” began to find its way. It was finally happening — more than 20 years since “Clueless” hit movie theaters, it was finally happening. (The show, now in previews, opens on Dec. 11 at the Pershing Square Signature Center, in a New Group production.)

Which is great — it is — but it’s also a little nuts. Heckerling was a pioneer as a female director of touchstone ’80s comedies like “Fast Times at Ridgemont High,” “National Lampoon’s European Vacation” and “Look Who’s Talking.” She was a woman who was somehow able to join a fraternity and thrive in it. And yet, lately, she’s been relegated to directing episodes of other people’s TV shows. But now, she is re-emerging, with a new show made from an old movie — which is great news, truly. But it all raises the question of where she’s been and why her career seemed to halt after “Clueless.” Maybe “Clueless” was her masterpiece and she had nothing to say after it. Or maybe she got tired of dealing with all the ways that trying to have creative output can diminish you in the world. The complicated answer is that she doesn’t quite know.

“CLUELESS” CAME TO HECKERLING in waves throughout her life. Some of the plot was based on Jane Austen’s “Emma,” which she read in a lit class when she was in film school at New York University. She also remembers an episode of “The Patty Duke Show,” where a dorky exchange student gets a makeover and learns how to be cool. All of these things passed through Heckerling’s cerebrum and assigned themselves to a character who would eventually come to life as Cher.

Mainly what she was trying to do while writing Cher was to just spend time with her. It was the same way she felt about Jeff Spicoli, the slacker nonpareil in her 1982 directorial debut, “Fast Times.” Or Lorelei Lee in the novel, “Gentlemen Prefer Blondes.” Or Emma. Or Patty. She was drawn to their sunniness. “I like characters that are optimistic, even if there’s no reason to be optimistic,” she said. “And I thought, what if there was a girl in high school …?”

She told me this the first time we met. This time she was a wearing what a milliner friend of mine called a “variation on a Victorian mob hat.” A tote bag from the Brooklyn Endoscopy and Ambulatory Surgery Center was on her lap. She wore black pants and a Marvel belt that featured Captain America, the Hulk, Thor and Spider-Man. I asked her why she was wearing a Marvel belt, and she said, “Because my pants keep falling down.” Her phone’s home screen is a picture of Peter Lorre screaming, because, she said, “That’s how I feel when my phone rings.”

The positivity and shine of a Cher was such anathema to her. She’d been miserable in school. She’s a pessimist, she said, “the opposite” of Cher. She wanted some relief; she wanted to spend time occupying the head space of an optimist who thought everything might work out, who wasn’t plagued with self-doubt, who seemed confident and self-assured. She thought maybe if she spent time with that kind of character, it would take — like an organ transplant or something.

Heckerling had known Art Linson, a “Fast Times” producer, for a while. He’d seen Heckerling’s short, “Getting It Over With,” which was about a girl trying to lose her virginity the night before both her 20th birthday and her psych final. He showed the short to his fellow producers and Cameron Crowe, who wrote “Fast Times,” and they knew.

“She had no fear,” Crowe said, sitting two floors beneath her at the New 42nd Street Studios, working on a musical adaptation of “Almost Famous.” “She was completely jacked about the material.” She was 27 at the time. She knew the truth about kids. She had such a clear vision, he said: That the movie should center on a mall, that there should be surreal shots, like the kids smelling their dittos. She wanted to show Stacy’s abortion. She wanted to show nudity. “I mean, she was like a European freaking director.”

The studio told them it would never work. They said you needed something nostalgic when you wrote about kids like, “American Graffiti.” It was released in just 498 theaters. But something happened the weekend it went to screen. People loved it. The studio released it into more theaters in coming weeks, and “Fast Times” became a Top 5 movie.

“Johnny Dangerously,” her 1984 follow-up, was about gangsters in the 1930s — her favorite genre, equal only to musicals. But the movie was testing poorly, and she was worried about her future. “I thought, well, men can have a failure. Women can’t, and so I have to have something that will make money, and it has to already be in the works so that they’ll discount ‘Johnny Dangerously’s’ failure.”

She jumped on “European Vacation,” a sequel to a successful film, with Chevy Chase and Beverly D’Angelo, both of whom she had nothing to say about. (“I don’t like saying bad things about people.”) She hated it. “Oh my God, I despise that movie. I just felt very, like, I don’t know if I even want to ever do this again.” Then, after “Johnny Dangerously” came out, she said, “I wanted to kill myself.” The theaters were empty, and she felt sick. She didn’t realize she felt sick because she was pregnant.

She had promised herself that she would not have a child until she’d directed three movies, and there she was, three movies under her belt, and now a fetus there, too. She gave birth to her daughter, Mollie, during her second marriage, to the screenwriter Neal Israel.

One day, soon after Mollie was born, and soon after she found herself no longer married for a second time, she was thinking about what life might look like to her baby. She imagined an ongoing monologue in Mollie’s head. Was this a movie? She and Israel batted it around as a movie idea. She thought no, it was corny. But eventually she began to consider it: a talking baby who observed its single mother as she tried to figure out her love life. She made the baby a boy so that she could fool the studio into not realizing that this was actually a movie about a postpartum woman’s love life. Or about Heckerling herself. Mollie’s father is not Israel, but the director Harold Ramis. If you would like more details on this, you can watch “Look Who’s Talking,” which is a fairly accurate account of the whole thing.

Anyway.

“Look Who’s Talking” (1989) was a massive hit, but the success was tinged with ugliness — it triggered a lawsuit, the terms of whose settlement were confidential. She ended up doing the sequel, though she didn’t really want to.

She became depressed. She didn’t know how to feel better, but then — picture the Electric Fountain in Beverly Hills lighting up behind her — “Clueless!”

She wrote “Clueless in California” for 20th Century Fox, but she said the studio had too many notes on the script. It had just released “PCU” and “Airheads,” which hadn’t done as well as it hoped. She took it everywhere else, and finally to Paramount. Heckerling loved MTV, and she handed the script over with a VHS tape of Alicia Silverstone in the Aerosmith video for “Crazy.”

“Clueless” opened at No. 2. “In the midst of a summer of mostly desultory films, along came ‘Clueless,’” wrote The New York Times. “The wickedly funny farce about rich teenage girls in Beverly Hills emerged this weekend as a sleeper hit of the summer.” Heckerling told a reporter at the time that she was “blown away” to have a hit on her hands, but the box office was nothing compared to the movie’s afterlife. It spawned a TV show that ran for three seasons and a series of 21 novelizations (Sample title: “Cher’s Guide to … Whatever”). Two decades later, it is still hard to find a weekend where “Clueless” isn’t playing on cable.

“One of the things that I think is very clear in her work,” Rudd said, “is just how much she loves young people and doesn’t talk down to them, and treats the things they’re going through with respect and a relatability that she never seems to have lost. So there’s something kind of timeless about her work and about her.”

Crowe remembers the opening weekend for “Fast Times,” the teen classic that would disprove the studio’s skepticism. Crowe went to see his predicted failure of a movie in the theaters, and afterward, he called Heckerling, who was sitting at home, sad. He said, “Go see the movie.” So she dragged herself to a theater and listened to the audience recite lines at the screen. People knew the dialogue, as if they’d already seen it multiple times in its first weekend.

She didn’t know what to do with that success. “That’s the Amy combo,” Crowe said. “It’s the happy/sad. It’s the beautiful combination. It’s like, humble, and self-deprecating, and wildly original and eccentric at the same time.”

She tries not to think about moments like that one too much. She puts them in a jar, and every now and again she takes them off a shelf and opens them up.

Now she’s on 42nd Street with her musical, which takes pop hits from the ’90s and revises the lyrics. She remembers coming up from the subway in a stroller and seeing Times Square for the first time. A camel smoking. A 7Up pouring. The signs were alive. The place was alive. She thought this must be the center of everything.

“Clueless” was back where it belonged, in Heckerling’s hands, which was a relief. The year after the movie left theaters, Heckerling signed on to write and direct episodes of the “Clueless” television show for ABC. She has read the novelizations; she watched that Iggy Azalea video that she thought was cute, but still. This year a show called “The Unauthorized Musical Parody of Clueless” was mounted at a lounge in Los Angeles, which annoyed her to no end. (“I called my lawyer. He said it’s parody. I said, ‘So then can I steal everything I want and make parodies?’ Because I have a lot of things I would like to parody.”)

People don’t really understand that “Clueless” is hers. “Clueless” shouldn’t be something you can mimic and reference and repeat and extend for a quick dollar. That’s what these people never understood. “Clueless” is there to save your life.

IF SHE CAN, Amy Heckerling writes all night and sleeps until 2 p.m. She’s heard that night people don’t live as long, but she read somewhere that when we were all tribes running around together, some people, the nervous types, were tasked with staying up all night to keep guard and serve as human alarm clocks. That’s her, she said.

She lives on the Upper West Side with her 83-year-old mother and Mollie; Mollie’s boyfriend; and their 4-year-old daughter, Harper. She’s happy to be back in New York, where she doesn’t have to drive all the time. She didn’t even know how to drive when she arrived in Los Angeles all those years ago. She lost count of how many times she failed the driving test before she passed.

Upon waking, she makes her mother food. If they don’t have a doctor’s appointment to go to, she exercises on the treadmill, where she watches what she calls “Law & Order: Sexy Victims Unit” or “the Nazis,” which refers to whichever documentary on the Third Reich is playing on TV at that particular moment.

At night, she writes longhand, on the backs of old screenplay pages, so she doesn’t waste paper. Or, she’ll watch one of her favorite movies: “A Clockwork Orange,” “Mean Streets,” “West Side Story,” “Bye Bye Birdie,” “8½,” “Blazing Saddles,” “Bicycle Thieves.”

When Heckerling was attending the High School of Art and Design in New York, she had to write an essay on what she wanted to do when she grew up. She was not raised to believe she’d do great things. Her father, who was an accountant, was upset that she didn’t learn how to type. She still can’t type.

She wrote in her essay that she wanted to be a writer for Mad Magazine. But the kid next to her wrote that he was going to Hollywood to make movies, and that made her angry. “First of all, he copied off of me all the time,” she said. “What was he going to do in Hollywood?” She decided that she would be going to Hollywood to make movies.

In the ’80s, she read an article about slob comedies, which included “Fast Times,” and was immensely proud of being the woman amid all the men behind them — “like ‘Police Academy’ and ‘Animal House’ with young people behaving badly or stupidly or whatever and raunchy humor.” “I was the only female that did a slob comedy, and I was kind of proud. They’re saying these movies are stupid and they’re lowering the art form and raunchy. I’m going, ‘I’m the only woman.’”

She always tried to act like she lived and worked in a post-sexist world. She hears things now about people not getting hired because they’re women, and in her own case, all she can think is: “Oh, I don’t know. You know, I keep thinking, like, well, it’s my fault. If I was better, it wouldn’t have happened. 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.”

After “Clueless,” she wasn’t sure what to do next. Before that, she’d always had goals. She wanted to make a big studio film before she was 30, and she did that. She wanted to make a hit — “the way boys had hits, not like a girl hit that made $50 million, but a boy hit that made hundreds of millions,” she told Charlie Rose, and she did that. Now she decided that she would focus on the stories she really wanted to tell.

She made “Loser,” a romantic comedy starring Jason Biggs about a misfit college student, in 2000. She made “I Could Never Be Your Woman,” starring Michelle Pfeiffer and Rudd, about a divorced mother dating a younger man, but for complicated business reasons it went direct to video. In 2012, she reunited with Silverstone for “Vamps,” a movie about a vampire named Goody who has been stuck as a 20-something for hundreds of years.

Silverstone said that “Vamps” showed what heart there is in Heckerling. “These characters are really interested in fashion and clothing and looking a certain way in ‘Clueless’ and in ‘Vamps,’” she said, “but they also are really battling with deep things — you know they’re trying to be good people. They’re deeper questions that are put in a really sweet, silly, fun setting.” “Vamps” went straight to video.

You can think of Heckerling as being less in demand than she should be simply because she’s a woman, and you’d be sort of right. But it’s hard to know what held Heckerling back from a more prolific career because she’s so singular in both her tastes and her temperament, and because she had success so early on. “Amy predates the problem even,” Crowe said. What he means is that Heckerling was being hired before anyone was really even asking why women don’t get hired, so how do you apply these questions to her? Heckerling was hired, so wasn’t the game hers to lose?

But there are other ways to be sexist than simply not hiring a woman. Heckerling’s movies got dismantled at the edges: The studio wouldn’t fund a soundtrack. It would release the movie into a tiny amount of theaters, and then you don’t get hired again because your last opening flopped because it opened in a tiny amount of theaters. Distribution deals would fall apart.

To all this, Heckerling said: “I mean, I don’t know, maybe they just don’t like me. You go, well, maybe if I had been more brilliant and thought of better solutions, it would have come out great, or maybe if I, you know, was, like, more of a schmoozer and knew how to work with people? But I don’t, and I depend on other people to do that, and I’m not a wheeler-dealer. I’m, like, a middle of the night scratching on paper person, and so I feel like it’s my fault.”

So according to her, maybe if she had been a better director, or something, she would have been hired more. Or maybe, as Charlie Rose told her: “I talk about you as one of the mainstream top-line female directors.” Or, according to Bob Thomas, writing about “European Vacation” for The Associated Press in 1984: “Amy Heckerling seemed miscast as director of the $17 million comedy … She is slender to the point of being slight, and she seemed lost amid the cluster of technicians around the camera. But when she commanded ‘Action!’ and ‘Cut!’ there was no doubt who was in charge.” Or, according to Roger Ebert, after seeing “Fast Times:” “If this movie had been directed by a man, I’d call it sexist. It was directed by a woman, Amy Heckerling — and it’s sexist all the same. It clunks to a halt now and then for some heartfelt, badly handled material about pregnancy and abortion.” I could have filled this entire article with a list of these things.

Sexism in Hollywood doesn’t always mean not being hired; it doesn’t always mean that you were sexually harassed. Sometimes sexism is a plethora of compliments that make your brilliance a constant exception. Sometimes sexism is taking someone who has self-doubt, like many creative people do, and yielding to it, instead of propping her up. Sometimes sexism is taking the extremely relatable content of a person’s soul and not being able to figure out why it would be worth the trouble to release it — not taking seriously the women who would find comfort and release in a movie that so clearly understood their complicated emotions. You do this enough times, the self-doubt turns out to have been a prophecy. There Heckerling was, making movies about her experience as a very particular and very regular kind of woman: A woman who had been scorned, a woman raising a child, a woman who would stay up all night if only you’d let her. But things would go wrong, as they often do in moviemaking, and in her case there would be no executive or producer who would rescue her project.

But Heckerling? All she can ask is, “What did I do wrong?” All she can think is that if she were better, she’d be working more.

Here’s how “Vamps” ends: Goody is tired. She’s tired of learning the new technology. She’s tired of youth. A series of events force her to rapidly age. She says, “I want to be in the center of things,” which means back to Times Square, where she remembers her whole life. She sees Broadway as it was before it was “Broadway,” then she sees it as it would have been when young Amy Heckerling saw the lights for the first time. She sees the people she’s loved through the years, and in her face there is something of an understanding: that all her contributions to the world will live on, maybe in different forms, but that’s the right order of things. She turns to dust, and the wind carries the dust away and all through the city; the things she’s created go forward with a piece of her attached forever and ever. She is able to move on and blah blah blah. Maybe some day.

AMY HECKERLING, the creator, writer and director of “Clueless” — the person who invented Cher Horowitz because she so badly needed her — learned of Paramount’s impending remake of “Clueless” a few weeks ago, at the same moment the rest of the world did, or maybe slightly later: She got texts from Silverstone and Stacey Dash (who played Dionne in the movie) saying something to the effect of: WTF?

She was ready to object to the remake, but her lawyer looked into it. Paramount had the right to remake the property after seven years without consulting her. Because she wrote it, she’ll get “mailbox money,” as she calls it — meaning a check will show up. But other than that, it’s just not hers anymore.

She thinks about Harold Ramis, who is no longer alive. A lot of people objected to the female remake of “Ghostbusters,” some because they’re sexists. But she also had a moment when she felt a proprietary possessiveness on his behalf. “Yeah. I felt like oh, my God, how could they? And then I went: Get over it. I don’t know if he would have been upset or not. It doesn’t take away from what he did, whether or not the female version is good or bad.”

She understands the “Clueless” remake. New ideas are risky. Things with brands aren’t, which is endlessly ironic to her — that the things that were begrudgingly released years ago could possibly become no-brainers to some lucky director now. She’s trying to think of it the way she thought of “Ghostbusters”: That the new “Clueless” won’t take away from her “Clueless.” It’s not so easy. It doesn’t come naturally to her. Not yet. Do you see why she can’t yet give up Cher?

So Amy Heckerling, the original virgin who can’t drive, continues to try. She participates in the ultimate act of optimism: the creation of an actual musical, where her characters, who shine with forward motion and positivity, burst into song, just like they’re supposed to — a musical, where all emotions are valid and celebrated. Her characters live in a world where hard work is rewarded, and love and appreciation and gratitude come to people who deserve it. In the studio on 42nd Street, they take it from the top again. Maybe this time.

Anyway.