Clueless turns 20 this month, but Cher Horowitz remains timeless. The miracle of Amy Heckerling's iconic retelling of Jane Austen's Emma is that it never feels dated and it never fades from American cultural consciousness. To this day, an all-yellow ensemble still triggers visions of Alicia Silverstone debating the rights of Haitians. The film also features what is probably the best reference to Monet in all of cinema. Clueless sits as a merry flag in the jaded drought of 90s youth culture. In an era when the prevailing mood was just that – moody – Clueless was shamelessly optimistic.
"I think what [director] Amy Heckerling was able to do – and this is very hard – is make the film satirical, but at the same time not mean-spirited," said Jen Chaney, author of As If!: The Oral History of Clueless. The book, released this month by Simon & Schuster, is the first in depth look at the film from inception to reception.
"The thing that struck me about Clueless when I saw it – and I wasn't necessarily in the film's target demographic – was that it reminded me of how I felt ten years earlier when I was [a teen]," said Chaney.
This sort of cross-generational appeal is key to the film's power. In the book X Vs. Y: A Culture War, a Love Story, authors and sisters Eve and Leonora Epstein tackle the nuanced taste and trends of two generations: Gen X and millennials. Clueless finds its sweet spot at the centre of the book's Venn diagram: The two generations manage to love the film equally.
"I think the film really represents the younger generation falling in love with Gen X and vice versa," explained Chaney, quoting the book's broader thesis about the romance between Cher and her former-stepbrother Josh (Paul Rudd). "It's about the merger of these two ideas. And I think that Josh does represent what we were seeing not just with teens, but youth culture in general at that time. He was more emblematic of what the prevailing pop-cultural tone was, as far as young people were concerned."
If there is connective tissue that binds Austen's work with Heckerling's script, it's the inventive use of language, precise and exaggerated at once, flowing from the mouths of sharp-witted women.
Watching Clueless in the context of its time is a bit like watching a dream sequence in the middle of a drama. Alicia Silverstone plays Cher with a lightness that makes her feel like the cheery older sister for an entire generation of disgruntled ennui – she's a warm hug in a mosh pit. Cher's steely self-determination, which shines through as she negotiates her report card, sets up her teachers in order to bring up the class average, and finds a potential love interest for her new friend Tai (the late Brittany Murphy) could be read as a cunning use of feminine wiles. However, it's her firmly rooted sense of self that embodies the character's strengths.
"Even with riot grrrl and all that, I don't think that in 1995 young girls were growing up with that sense of confidence embedded in the culture," notes Chaney. " Clueless feels like the vanguard of a type of feminism in which you can have complete confidence in your own self-resilience and identity while still wanting to shop."
It helps to have source material as beloved as Emma, considered by many to be Austen's masterpiece.
"Emma is fascinating because it's about a woman who isn't likeable," said Marilyn Francus, an English professor at West Virginia University, and the recent recipient of the Jane Austen Society of North America International Visitor Fellowship.
"Emma is bossy and she likes to control her world, and she can be demanding," Francus told VICE. "And yes, Cher is adorable from the beginning, and because we get voiceover, we as viewers are aligned with her from the start. But to see a character like that develop is masterful."
If there is connective tissue that binds Austen's work with Heckerling's script, it's the inventive use of language, precise and exaggerated at once, flowing from the mouths of sharp-witted women. Cher doesn't just get denied, she gets "brutally rebuffed"; when Dion's boyfriend gets called out for repeatedly calling her "woman," he delivers what amounts to a soliloquy on the legitimisation of street slang. Tai's response – "Shit, you guys talk like grownups" – both nails it and misses the point.
"Both Austen and Heckerling love their female characters for their messiness, and both are really good at exploring female relationships, especially through language," Francus explained. "The use of language in Clueless is so smart and so unique. It introduced a level of idiom that has withstood the test of time, which you wouldn't necessarily expect."
Though Austen's work has been celebrated for over 200 years, the prose of teen films hasn't had quite the same level of longevity. Phrases like "fuck me gently with a chainsaw" from Heathers never found a foothold in teen-speak; the failure of "fetch" seems a bit like a self-fulfilled prophecy; and the overload of quirk in Diablo Cody's script for Juno quickly became both the film's calling card and fodder for its detractors.
"Amy did a ton of research and has always been a keen observer of how people think, and has kept her own slang dictionary," Chaney says. "Somebody knew what they were talking about, and you could tell. So that's part of her observational acumen."
This fusion of imagination and reference also fuelled the film's other notable contribution to popular culture: its iconic costume design, crafted by the singular Mona May. May met Heckerling early in the development of the script (then written as a TV pilot), and the two immediately hit it off. Their creative relationship seems to have stayed pretty steady; May is currently slated to develop the costumes for Clueless's recently announced Broadway adaptation, which Heckerling is also writing.
"We didn't want to shy away from being girly," said May, who actively wanted to avoid the era's emphasis on side-eyeing fashion. "We wanted this innocence; they weren't walking models to us. The clothes were never wearing them. It was just an extension of them coming alive."
Speaking of fashion, check out our doc 'Iran's Fashion Revolution':
Clueless isn't quite ahead of its time – the film didn't predict trends as much as dictate them – nor is it a time capsule of the 1990s – even at its most grounded, everything Cher and Dion rock veers into the same type of fantasy that Patricia Fields would infuse Sex and the City with. Instead, May culled from the past to create something entirely other. Those knee-high stockings? 1920s Clara Bow. Shift dresses with cap sleeves? Think Jane Seymour in the 1960s. Throw in some quintessential schoolgirl pieces (Mary Janes, vinyl, plaid skirts), and you have a design that manages to eclipse an entire decade's worth of trends without once feeling like anything distinctly 90s.
"What was great about working with [Heckerling] was that she was like a phenomenal fashion editor, where she would push me and say, 'What else you got?' and also know when to pull back and stop," said May. "For that first outfit, we knew red was too bold, green was something Cher would never love, blue wouldn't pop. And we knew that it was her first day of school, she would want to stand out. That yellow plaid piece wasn't us trying to be cool or use Cher as a mannequin. It was something that felt true to what this character would love."
More than anything else, the fashion in Clueless serves an interesting aesthetic purpose in that it aids the film's subversion of genre. While most teen films frame the popular girl as a type of antagonist, Clueless frames Cher as not just worthy of our love, but as emotionally and intuitively insightful. These characters are, upon first glance, seemingly vapid and removed from any recognisable reality (the film's title referring both to an inability to run their own lives and a lack of understanding for how the other half lives). But the girls' clothing hints at something more creative, eschewing brand names in favour of originality. Their taste immediately establishes these women as worthy of deeper consideration.
"When the movie came out, the time was right," said May. "Girls were ready to shed the plaid shirts and baggy pants, and to return to fashion as a kind of special creativity. People wanted to embrace a kind of hopefulness through their dress with loud colours. They wanted to return to a kind of innocence and beauty."
The film's contribution to popular culture is its perfect storm of feminism, classical allusions, and pure wit, with a genuine affection for both the women on the screen and off.
This is the thread that runs through Clueless: the film's relentless optimism in the middle of an epoch-defining decade. "It's everything from Ren & Stimpy to the US occupation of the Middle East – you're part of a larger cultural and political world that helps make the movie both timely and timeless," Francus said. "And in that sense, Heckerling is picking up on some of the same things that Austen is. How is it that these novels are still speaking to people around the globe some 200 years later? It's because they get at something broader and speaks universally. It's a kind of genius."
Now more than ever, in a cultural climate pushing for feminism and equal representation both on-screen and off, the girl power on display in Clueless finds continued relevance. Heckerling wrote and directed; Silverstone signed a much-discussed $10-million contract with Columbia afterwards that contractually positioned her as a producer.
"After 1995, you see more and more women asserting themselves as feminists," said Chaney, "even if they didn't fit into some preconceived idea of what a feminist was. I think that might be a way Clueless still holds up. That idea of feminism is one that people are much more invested in and can buy into now, as opposed to the first time around."
Clueless has endured as the 90s' most distinct product, yet has managed to hold separate from the era's nostalgia. The film's contribution to popular culture is its perfect storm of feminism, classical allusions, and pure wit, with a genuine affection for both the women on the screen and off. Even 20 years later, its reputation feels remarkably in place – a brilliantly constructed work in a culture that looks fine from far away, but up close is one mess. A total Monet.
Follow Rod on Twitter.