The Director of 'Clueless' on Ditziness, Dialogue, and Dating Your Stepbrother

It's a testament to the strength of Heckerling's script that Clueless has proven to be both as timely and timeless as its literary big sister—the film is a re-working of Jane Austen's Emma. Lifting the story from the manor houses of 19th-century England and plunking it down in Beverly Hills, the epicenter of "contempo-casual" teenage cool, Heckerling managed to preserve the spirit and satirical wit of Austen's novel while simultaneously penning the vernacular of the decade. Perched on the edge of its 21st birthday, the film will be screening in 35 mm alongside Heckerling's Fast Times at Ridgemont High at New York's new Metrograph theater this weekend as part of a retrospective of the writer-director's work. As much as the movie is a perfectly preserved time capsule of pop culture, in 1995, Clueless also provided its adolescent audience with something to grow into. If they were slightly too young to appreciate the subtler notes of the film's playful eye rolls, double entendres, and slew of references—even as they quoted it endlessly—at the time, today, they make memes out of it.

Now 62, Heckerling says she never tires of talking about the movie. She takes credit where credit is due but will gladly admit that one of the film's most memorable moments—Cher's mispronunciation of "Haitians" as "Hat-ee-ans" in Mr. Hall's debate class—was a happy accident, courtesy of actress Alicia Silverstone. "It wasn't written that way in the script" Heckerling recalls, "but that's how she said it. Everybody started to run towards her to correct her and I had to kind of block them all, like 'step away from the actress!' I didn't want her to act; I just wanted her feel that confidence."

But there's a big difference between stupidity and cluelessness. "I didn't want [Cher] to be not intelligent," Heckerling explains. "I wanted her to just not know what she didn't know yet." Cher certainly doesn't want for wits. She may pronounce Spartacus as Spa-ra-ti-cus, mistake Billie Holiday for a man, and quote Cliffs Notes instead of Shakespeare, but she also casually throws down words like "capricious," "unequivocal," and "sublime" in her everyday conversation; she uses Monet as metaphor to dis her nemesis from across the room. ("It's like the painting, see: from far away it's OK, but up close it's a big old mess!")

Cher talks a lot—and she talks fast. She's quick with the quips, handy with the comebacks, and most importantly, she recognizes her verbal prowess as her primary means of power, even if she's a little misguided in the way she uses it. (Like Emma, Cher is preoccupied with matchmaking and meddling as a means of controlling her social universe). So although she's come to embody the quintessential Valley Girl (yes, yes, we know she's from Beverly Hills) she can be more productively characterized as a direct descendent of the fast-talking dames that populated films of the 30s and 40s. "Oh, that's pleasant!" Heckerling exclaims upon hearing this theory. "I'd like to think of her as Una Merkel's granddaughter."

Heckerling is clearly fascinated by language—slang, tone, cadence, and accents. Eavesdropping is not just part of her research process as a writer, but a way of life, and she still keeps a copy of the 1995 linguistics study she used as a reference point for Clueless within arm's reach at home in case she ever needs it. But for all her expertise on So Cal teen speak, she talks like a born and bred New Yorker: She lands hard on her T's and drops the H's at the beginning of words (so that "human" becomes "you-man"). She's stylish in a subdued, distinctly East Coast sort of way, typically clad in black (though today she wears a deep green blazer and white collared shirt) with the thick black eyeliner to match.

If this monochrome chic seems directly at odds with the film's candy-colored color palette, that's only a further credit to the breadth of Heckerling's interests, tastes, and references. Over the course of our conversation, she jumps from the Bowery Boys, to the poetry of John Donne, to Woody Allen, and espouses her love for pre-war Japanese cinema (she likes her Ozu) and Fritz Lang's M. She's also a big fan of American gangster films of yore and, unsurprisingly, classic musicals—she's currently working on a singing version of Clueless. In fact, the over-the-knee socks Cher and her gal pals made instantly trendy are a direct nod to Liza Minnelli in Cabaret. "She was singing 'Auf wiedersehen, mein herr.' I went nuts for those!" Heckerling says.

Both the filmmaker and her costume designer, Mona May, were (rightly) horrified by the whole 90s grunge thing at the time they were making the film. "I couldn't believe those [low-riding pants] were hanging on as long as they did," Heckerling says. "You'd look at guys and think, why would I want to see a belt below your tushie and think, ooh, he's cute… I would look at them and go, 'ugh!'" Sound familiar? Cue: "All the Young Dudes."

Eschewing oversized flannel for a more tailored, feminine look, Heckerling and May came up with some of the most memorable outfits of the past 20 years, making choices that were geared as much toward aesthetics as they were toward what might make for good dialogue. There was Cher's white collarless shirt from Fred Siegel—her most responsible-looking outfit; the red Alaia dress she gets mugged in; the white, skin tight, Calvin Klein her father tells her "looks like underwear"; her purple clogs; and who could forget Dionne's Dr. Seuss Hat (which was an infiltration of the grunge trend, a la the music video for 4 Non Blondes's "What's Up").

For all the film's commercial success and zeitgeist-shaping legacy, it was a long road from script to screen, with Heckerling having to jump many hurdles, including being encouraged by Fox to focus more heavily on the male characters. The whole pseudo-incestuous romance with Cher's stepbrother, Josh (played by a young Paul Rudd), also raised some red flags with executives. "That was so silly," the director remembers. "They were going, 'how can you have sex with your stepbrother?!' And it's like, they're not related: Their parents were briefly married and [Cher's] father is still nice to [Josh]. That's not verboten, you know?" Ultimately, Fox didn't make the movie, and Heckerling moved the script to Paramount. "I told Scott Rudin, here are all the things I used to have in the film, and he told me to put it all back."

What about the bullshit notion that "girls can't be funny"? Has that been a wall Heckerling has constantly smashed her head against in studios and writer's rooms? "Duh!" she says. With lines like "searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie," it's surprising and a little bit dismaying that Heckerling, a dialogist of the highest order, is not more readily mentioned in the same breath as filmmakers like Whit Stillman or Noah Baumbach.

For all those wondering about the etymology behind the "way harsh" insult "you're a virgin who can't drive": "Well, that was me!" Heckerling laughs. "For a very long time. You take the thing that embarrassed you most, and you use it."