In the early 1990s, the writer-director Amy Heckerling was feeling down. Heckerling had burst on to the scene a decade earlier with Fast Times at Ridgemont High, a groundbreaking coming-of-age comedy of libidinous teens, and scored a surprise box office hit with 1989’s Look Who’s Talking. But she was struggling to fit Hollywood demands. “I was thinking: ‘Oh, I’m never going to make a film that’s what I want it to be, because you can’t have protagonists that are female, you have to do slob comedies, but there’s only a few actors that they accept in those roles, and you don’t get a chance to work with them if you’re a female,’” Heckerling told me recently.
With little interest in catering to the prevailing tastes of the day, Heckerling went back to the drawing board: what did she want to write? A true native New Yorker with the accent to match, Heckerling “gravitated towards darker stuff” – early gangster movies, David Lynch. But she was most amused by “people who are very optimistic and happy. I just think, how the hell did they get that way?” Like the main character in the 1994 movie Ed Wood, perpetually pleased with his mediocre work, or the star of Gentleman Prefer Blondes (the book), sending herself flowers to stir the jealousy of men around her. She envisioned a woman in a “big, pink bubble that can’t be burst”, convinced of her centrality but still winsome, relentlessly positive and naive. Someone like Cher Horowitz, the most impeccably dressed 16-year-old in America, hapless social matchmaker of Beverly Hills’ Bronson Alcott high school and the lead of Heckerling’s movie Clueless.
Clueless, released 30 years ago on 19 July, remains a seminal teen comedy, the kind that immediately and indelibly stamps the culture. The instantly recognizable yellow plaid suit? “Whateverrrr?” As if you could escape its cultural legacy. A loose adaptation of Jane Austen’s 1815 novel Emma, Clueless reinvigorated the stagnant teen movie genre that flourished for the rest of the decade. 10 Things I Hate About You, Mean Girls, Easy A – the teen comedy staples of my teenage years in the late 2000s – live in the shadow of Clueless, which played almost daily on at least one cable channel after school. “There are very few movies in history that have lasted 30 years with that kind of intensity, with that kind of a broad appeal to generations,” Mona May, the film’s totally important costume designer, told me. “It’s truly beloved.”
“It’s bright heartwarming and joyful – smart, funny and satirical in a way that still resonates,” said the film’s star, Alicia Silverstone, via email. “There is something about Amy’s take on youth culture and coming-of-age stories that is timeless.”
It also barely made it out of pre-production. Finding a studio home for Heckerling’s script was, as Cher would say, “like searching for a boy in high school … as useless as searching for meaning in a Pauly Shore movie”. Heckerling first developed what she thought would be a TV series at 20th Century Fox, with the support of an executive named Elizabeth Gabler. She delivered the feature script to Fox along with a VHS tape she recorded off MTV of Aerosmith’s music video for Cryin’, featuring a young, blond, radiant actor named Alicia Silverstone. They passed. Heckerling’s agent, Ken Stovitz, then doggedly shopped the idea around town, to no avail. The protagonists were female; “Clueless” sounded too much like underperforming films on young slackers; studio brass thought Heckerling’s still distinctive amalgamation of Valley speak, teenage slang and personal inspirations (the trademark “as if!” came from “my gay friends in their 30s”) wouldn’t translate to a wide audience. “The entire industry said no,” Heckerling recalled.
Except for Scott Rudin, the prolific, and prolifically volatile, film and theater producer, whose support ignited a bidding war. “Usually I’d write something for some people and it would go where it was or we’d go to other people that might be interested,” Heckerling said. “But never, ‘we all hate it, now we all love it.’” And that’s show business – “it’s stupid,” Heckerling laughed, “but I love it.”
With the backing of Paramount, Heckerling and casting director Marcia Ross began their search for actors to play the most stylish high-schoolers in the US, including some unsuccessful sessions shadowing real students at high schools in Beverly Hills and the San Fernando Valley. (“These kids walked around in these baggy clothes. They look just looked hopeless,” said Heckerling, though they perhaps inspired Cher’s disdain for high school boys “in baggy pants and oversized T-shirts looking like schlemiels – bleurgh”.) Heckerling first met with Silverstone at a cafe and was won over by, of all things, how she leaned her body over a cup to use the straw rather than pick it up, a move that reminded her of her eight-year-old daughter. “When I first saw the Cryin’ video, my initial reaction was: ‘Oh, she’s a hot chick,’” said Heckerling. But after the first meeting, it was: “‘Oh, I want to take care of her.’” She connected with her vision for Cher – a girl who “thinks she’s all that and she’s acting like a grownup who knows everything, but there’s a child in her”.
Stacey Dash, a 25-year-old from New York, won the part of Dionne, Cher’s relatively more experienced best friend. Dash “was much more savvy already”, May, the costume designer, recalled. “She was sassy.” To play Josh, Cher’s intellectual, very undergrad-y stepbrother-turned-love interest, the team cast a fresh-faced actor named Paul Rudd. And for the “clueless” Tai, a homely new kid Cher mentors – and misleads – as part of her initiative of “good deeds”, Ross found a 17-year-old newcomer named Brittany Murphy. “Everybody loved her,” said Heckerling. Peppy, open-hearted, eager to help, Murphy was always the frontrunner for Tai, though she wasn’t confident in her chances. After a chemistry read with Silverstone, “Alicia was trying to tell me: ‘Oh my God, it has to be her,’” Heckerling recalled. “And I was already like: ‘Yeah, we know.’”
Filming commenced in November 1994, and proceeded over 40 days in Los Angeles like “a well-oiled machine”, said Elisa Donovan, who played Cher’s haute couture-loving frenemy Amber. (Cher’s assessment: “Do you prefer fashion victim or ensemble-y challenged?”) Fresh to LA with just a few TV credits, Donovan walked on to her first film set and “thought: oh, this is how movies work. Brilliant women write them and direct them. They’re in charge. They’re the ones who hire all the right people. They tell everyone what to do in like a fun and kind, but firm way. They know what they’re doing.” (On subsequent sets, she “learned pretty quickly that this was highly unusual”.)
Key to this environment was the partnership between Heckerling and May, who assembled the entire wardrobe for the film – 63 designer looks for Silverstone, 45 changes for the other principal actors, and all the extras’ outfits – for a budget of about $200,000 (about $413,000 today). “Amy is an amazing writer,” said May. “She wrote the blueprint for me – high school, Beverly Hills, rich girls, high fashion.” But in 1994, “everybody was wearing grunge,” not Alaïa – a Parisian designer May had to personally beg, via French translator, for the iconic red party dress, as they were out of money; the designer loaned it – May designed the peacocking feather jacket to complete the look – and got name-checked in the script.
May took clues from runway shows, sourcing looks from department stores, old collection books and magazines. The characters “had Daddy’s credit cards, they could go shopping at the runway shows in Paris or Milan or wherever”, said May, but the clothes had to communicate “real girls that then you can emulate and love” – elevated and chic, but also youthful, fun and innocent. Such as, say, a yellow plaid Jean-Paul Gaultier blazer May pulled off the rack at a department store, the third choice behind a blue and red riff on the classic Catholic school uniform. (Yellow is “a tricky color”, Heckerling noted. “It’s sunshine, but it’s also jaundice.”) Blue didn’t work, red was too Christmas. But the yellow one on Silverstone was a goosebumps moment – “Oh my God, this is Cher,” said May. “She’s the queen bee.”
It was through the clothes that Silverstone, then 18, transformed from budding environmental activist into airheaded, but well-meaning, Beverly Hills queen. “She was already saving animals and walking around in her sweatpants and flip-flops with two dogs in tow into the fitting. She was not Cher in real life,” May recalled. Silverstone confirms: “I was not one bit interested in fashion at that time personally, and my usual outfit was jeans and my favorite green T-shirt.” But, “I looked at Cher as being extremely confident and having a deep, healthy love of herself.”
The set, overall, was “just really fun and vibrant”, Donovan recalled. “It was all magic,” said May. “Amy is such a great director – she opened us up, she’s very collaborative, she’s very encouraging.” Silverstone, as the star, was a bit more circumspect: “I was in almost every scene, so I was working hard and taking the role seriously. When I hear about all the fun the other actors had, I get whatever the past tense of Fomo is.”
Filming wrapped at the end of 1994, and Clueless hit theaters seven months later, becoming an instant hit among the target audience – something quickly clear to Donovan, who was swarmed by a group of teens at a mall a fews weeks after release. It took longer for Heckerling to catch on. “I didn’t feel like it was like a big [hit] at the time,” she said. “I have friends that are [male] movie directors, and they have hits that are gigantic. I mean, Animal House and Beverly Hills Cop and Ghostbusters, those are big money-making movies. And Clueless did not make that much. It was a hit, but it wasn’t in every theater like that.”
But it did catch on, winning fans on the then booming home video market and launching an endless tradition of Cher Halloween costumes. “You always hope your movie is a hit,” said May, who went on to design costumes for Romy & Michele’s High School Reunion, Enchanted, The House Bunny and more. “Every film-maker will say that, but you just never know. It has to just be the right moment and the right time and the right culture. And this was all right.”
In true Hollywood fashion, the industry took some of the wrong lessons – instead of focusing on how the movie worked, or greenlighting more female directors, it spawned countless imitators. Afterwards, “it wasn’t like: ‘Oh boy, here come all the great scripts,’” said Heckerling. It was: “Here’s the script that’s this classic for teenagers, or that classic, but with teenagers.
“They only think you can do what’s been done,” she added. “It’s like they needed a big insurance policy. Movies are expensive, so they only want to make sure that if you did Emma in high school, why don’t you do Persuasion in high school?”
Also in true Hollywood fashion, Clueless has become valuable IP – the basis for a spinoff TV show with Dash and Donovan that ran from 1996 to 1997; a West End stage show; and an upcoming, still vague adaptation with Peacock from The OC and Gossip Girl creators Josh Schwartz and Stephanie Savage, with Silverstone set to reprise her role. Heckerling, an executive producer, declined to offer any details, citing prematurity and a well-earned development superstition.
The 30th anniversary once again brings up the original film’s still remarkable singularity, as well as the stark absence of Murphy, who died at the age of 32, igniting years of intense media speculation. “I always think about Brittany and it’s really hard to do any of this and not talk about her,” said Donovan. “She was so talented and just had so much energy and so vibrant … just this hummingbird, frenetic sort of energy, but also like, ‘everything’s great. I got it. No problem.’”
With the anniversary events, “It makes me emotional because I feel like she should be doing a lot of this, like she would be doing a lot of this,” she added. But the milestone – the kids of Clueless now old enough to have their own headstrong high-schoolers – offers an opportunity to remember, as Heckerling put it, “the goofy fun of it all”.
“People come up to me and say: ‘Your designs changed my life,’” said May. “To hear that in your lifetime, that something that you created has had an impact on people? It’s incredible.”