“What would Jane Austen do?”: Amy Heckerling on Clueless at 30

“It was so perfect and universal and not at all dated. It was of its time, but it all made sense in the present – which was the 1990s.” Director Amy Heckerling is talking about the novel Emma by Jane Austen, but she could just as easily be talking about Clueless, her 1995 adaptation of it.

The Beverly Hills-set saga follows the ditzy but well-meaning Cher Horowitz (Alicia Silverstone) as she tries to find direction (“towards the mall”) and searches for meaning (as useless as searching for it “in a Pauly Shore movie”) in her high-school existence.

Heckerling, speaking to us ahead of Clueless’s 30th anniversary on 19 July, was no stranger to the high-school movie, having directed the seminal 1982 film Fast Times at Ridgemont High – seminal in both senses of the word, with that Phoebe Cates scene acting as a sexual awakening for a generation. Heckerling arguably defined the modern teen-movie genre – a fact that she self-deprecatingly denies. Nor does she see Clueless and Fast Times as in conversation with one another. Whereas Fast Times was based on Cameron Crowe’s time going undercover as a high-school student, Clueless was pure fantasy. “It was more of a made-up, elevated world. A little bit prettier, a little bit nicer, a little bit gentler,” she says.

Cher’s unflappable idealism and bubbly nature is the polar opposite of Heckerling’s sardonic personality. “I thought of characters that interested me,” she says, namechecking Ed Wood in Ed Wood (1994) and Lorelei Lee in Gentlemen Prefer Blondes (1953). “They were very optimistic. I wanted to do something where a character was so positive that they were right, and so happy with what was going on, that you could not burst their bubble. That’s not who I am as a person, and I think it’s an amazing quality.

“I thought of all kinds of amazing jokes that could go with that personality, but I realised I needed a plot! I wondered where I had seen these positive characters before,” Heckerling continues, remembering the novel Emma from her college days. She imagined how the snobbery of Regency-era Highbury, the fictional town in which Emma is set, would translate perfectly to the socio-political landscape of Bronson Alcott High School, which Cher and her cohort attend. 

This includes Dionne Davenport (Stacey Dash), Cher’s bestie because they’re “both named after great singers of the past who now do infomercials” and “because we both know what it’s like to have people be jealous of us”. There’s also new girl Tai Frasier (Brittany Murphy); “Elton [Jeremy Sisto], in the white vest, and all the most popular boys in school, including [Dionne’s] boyfriend,” Murray (Donald Faison) – “ain’t he cute?” And there are various assortments of archetypes that Heckerling observed shadowing high-school students in Beverly Hills, chaperoned by a generous teacher named Mr Hall, who she paid homage to with the character of the same name, played by Wallace Shawn. 

One of Heckerling’s favourite scenes in Emma pivots on the question of “Who’s going to go with whom in which carriage so that they’ll have some time alone?” and this shows up in Clueless when Cher reluctantly accepts a ride home from Elton after the Val party, resulting in her being “sexually harassed, robbed… and forced to ruin her dress.”

“All of that worked perfectly for teenagers in Beverly Hills,” Heckerling says.

Any time she came across a roadblock, she’d think, “What would Jane Austen do?”

Heckerling also picked up on the vernacular teenagers were using at the time and seasoned the script heavily with phrases we’re still quoting today, such as “I’m outie,” “Whatever!” and the enduringly iconic “As if!”

In addition to the slang words that were popular at the time, Heckerling included Travis Birkenstock’s (Breckin Meyer) skater speak, and Yiddish and legalese from Cher’s lawyer father Mel Horowitz (Dan Hedaya), creating a “dictionary” for each character. “The way a character expresses that something is good tells you where they come from, what year it is, how wealthy they are,” she says.

Clueless gets a lot of flack for popularising ‘valley girl speak’, uptalk and the vocal fry, but it’s part of Heckerling’s fascination with the fluidity of language. In possession of a thick New York accent herself, which she says has led people to assume she’s dumb, there are no doubt parallels with misconceptions about Cher’s intelligence.

“I wanted Cher to sound like someone who was trying to [be] very educated and mature,” says Heckerling. “She’s not just using those words, she’s looking for big words.” Like ‘sporadic’, which I, along with Tai, learned the meaning of by watching this movie. “You guys talk like grown-ups,” she exclaims.

It’s part of Cher’s need to gain “control in a world full of chaos”. “[Cher is] somebody who is so busy moving people around because she’s so afraid to do anything herself. She’s afraid to put herself out there for real,” Heckerling says. “She wants to be the one who controls, because it’s too scary to be one of the real people out there.”

It’s painfully relatable for many people on the cusp of self-discovery and, indeed, one of the reasons viewers are drawn back to Clueless for repeat viewing. 

One of Clueless’s triumphs is that it takes teenage girls seriously. Again, Heckerling demurs when I bring this up, saying that she didn’t think of or intend for Cher to be representative of her ilk. But Clueless meets young people where they’re at through conversations about pop culture, fashion and shopping. Clueless educated a generation on Calvin Klein, Fred Segal (RIP) and Alaïa – “a totally important designer” – which Heckerling likens to “playing dolls” with costume designer Mona May. Together they wanted to play into that fantastical element to contrast how girls were actually dressing at the time, “in baggy pants and oversized t-shirts looking like schlemiels – bleurgh.” No doubt the inspiration for Cher’s screed against the skater boys at her school.

To paraphrase Cher, that’s not all Clueless is about, though. New audiences are finding parallels in the Gen Z sex drought (“you’re a virgin who can’t drive”), ICE raids (“it does not say RSVP on the Statue of Liberty”) and as a love letter to Los Angeles after the turmoil that city has faced this year. This was not New Yorker Heckerling’s intention, who instructed her art director to construct “fake Europe”, with faux classic “pile[s] of bricks” plastered with Tudor-style columns that “date all the way back to 1972”.

Heckerling’s modest personality is apparent throughout our interview, and perhaps this is why she is still bemused by Clueless’s legacy. Or perhaps it’s due to a career spent having to constantly prove herself, like Cher. (We speak on the day the New York Times released their greatest movies of the 21st century ranking, which Heckerling was asked to vote in, but they did not include any of her comments.) Heckerling struggled to gain a foothold in the industry prior to Fast Times, and then Hollywood executives tried to pigeonhole her with more high-school comedies. 

She knew she couldn’t get her script for Look Who’s Talking, the 1989 pregnancy comedy starring Kirstie Alley, made due to a lack of interest in films with female protagonists, so she Trojan horsed a male-led comedy with Bruce Willis’s voiceover and John Travolta playing the expectant father to a pregnant Alley and, voilà, Look Who’s Talking was a film about a woman that spawned two sequels. 

After the success of Clueless, Heckerling was sent more screenplays about girls losing their virginity (“Give me a break, that’s so gross!”) and observed a rash of films in a similar vein that mostly focused on throwing the names of fashion houses around rather than keeping the focus on character development. “It seems like a lot of people were taking the wrong message,” she says.

Ultimately, Heckerling has not been able to reach the heights of Clueless again. “They weren’t coming to me with big action movies, because what did I have? A girl who was scared to drive on the freeway! I’m not your go-to person for big battle scenes,” she chuckles. “I tried to keep my mouth shut and be a good team player but I don’t care anymore – the industry was fucked up,” she continues. 

Maybe that’s why she keeps returning to arguably her biggest film, adapting it for a three-season TV series in the late 1990s starring much of the original cast (there’s a development deal for a reboot in place at Peacock – however, Heckerling remains quiet about her involvement), as well as two musicals: a jukebox off-Broadway effort starring Dove Cameron in 2018, and a new one with original music and lyrics currently showing on the West End. “Learning a new set of skills with a whole new group of people is pretty exciting,” Heckerling says of remixing her movie as a stage musical.

Ever the anti-Cher, Heckerling still can’t quite believe that people are still hungry for Clueless all these years later: “I never thought people would say nice things about me.” But she gets a kick out of hearing lines she wrote “out in the wild”, like someone next to her in a gallery remarking upon a French impressionist painting by said artist as a “full on Monet”, or party-goers doing “a lap before we commit to a location”. “Something of you is out in the universe, and that’s nice.”