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Clueless turns 20: 6 way existential lessons it taught us

Cellphones and plaid skirts: still in style!
Cellphones and plaid skirts: still in style!
(Photo by Paramount Pictures/Getty Images)
Tanya Pai heads the standards team at Vox, focusing on copy editing, fact-checking, inclusive language and sourcing, and newsroom standards and ethics issues. She’s also a founder of Language, Please, a free resource for journalists and storytellers focused on thoughtful language use.

Twenty years ago this week, a little film named Clueless hit theaters and changed pop culture forever. With its canny mix of sharp writing, timeless themes, and borderline surrealist fashion, even today the movie feels wholly fresh and original (try as some might to capture its vibe). But don't write off Clueless as just another teen movie. For members of a generation who watched it during their formative years (and then rewound it and watched again and again), the seemingly flighty comedy revealed some way existential truths.

So in celebration of its 20th birthday, here are six lessons to learn from Clueless.

1) Sincerity can be a boon, not something to be looked down on

The '80s and '90s were a prime era for great teen movies, and Clueless is often lumped in with 1988's sharp satire Heathers, which shares a focus (popular high school girls) and certain elements (hyper-stylized dialogue and costumes) but in tone is the pitch-black yin to Clueless's sunny yang.

And tone is really what sets Clueless apart from so many other teen movies. It's plenty funny, and it's not afraid to wink at its characters' occasional lack of perspective. (The movie's harshest insult, after all, is "You're a virgin who can't drive.") Yet the film's overall tone is one of sweetness. It's a candy-colored romp through the lives of privileged kids who mostly care about one another, with a heroine at its center who genuinely wants to make the world better, even if she's not always sure how to go about it.

As Clueless writer-director Amy Heckerling says in Jen Chaney's oral history of the film, part of what attracted her to the story was the sunny nature of its lead: "I remember reading Emma [the Jane Austen book the film is loosely based on] and Gentlemen Prefer Blondes. Those characters: what I gravitated to was how positive they could be."

She elaborated to the Telegraph:

I had always been interested in a character who is extremely optimistic, and what it would be like to be the kind of person who didn’t have any self-doubt. So I wrote Fox a pilot about this very happy character, Cher, and they didn’t want to do it.

Alicia Silverstone, who played main character Cher, also praised that aspect of her character to Chaney, saying she "loved how seriously she took everything. ... She was so sincere and so serious. And that's what I think makes her so ridiculous and lovely all the time."

2) Comedies starring women can do gangbusters at the box office

Already, 2015 has seen several high-profile and hugely lucrative comedies starring, written by, and directed by women — Elizabeth Banks's directorial debut Pitch Perfect 2 raked in more than $180 million domestically, and Amy Schumer's Trainwreck gave director Judd Apatow his second-best opening ever. But studios continue to balk at women-led films (see: the leaked Sony emails about why female superhero movies are a terrible idea for a particularly potent example).

Heckerling struggled with the same problem. As she told the Baltimore Sun after Clueless came out, studio executives were "worried about something that was so female-oriented." She said the studio "kept pressuring me to create more of a life for the boys in the film, to create more of an ensemble piece, which didn't make sense to me at all."

The idea for Clueless went through several iterations, beginning as a TV series, then getting turned into a feature film at the advice of Heckerling's agent, Ken Stovitz, then getting rejected "so many times it was a joke," according to Stovitz.

Luckily, like Cher arguing her way to a better report card, Heckerling and Stovitz persisted — and finally got their screenplay picked up after big-time producer Scott Rudin gave it his stamp of approval. On a $12 million budget, the movie went on to gross more than $56 million domestically, inspire a three-season TV show, and occupy a permanent place on home video and in the pop cultural canon.

3) A film can have a diverse cast without turning into an after-school special

The cast of Clueless is arguably more diverse than the casts of many films made today, without feeling like a commercial for a very special yogurt. Sure, Dionne (Stacey Dash) could technically be considered an example of the "black best friend" trope, but she gets her own plot lines and character quirks wholly outside of Cher.

As Grantland's Molly Lambert wrote:

It wasn’t until later that I realized how unusual it was to see black teenagers onscreen at all, let alone rich ones. Since so many movies, particularly movies set in a fictionalized dystopian Los Angeles, enforce the idea that diversity leads to conflict, it’s still refreshing to see a movie like Clueless suggesting that racial diversity in social settings like high school leads to the normalization of that diversity. The students at Bronson Alcott are extremely wealthy, but in Clueless’s L.A., that wealth knows no color boundary.

Then there's Christian (Justin Walker), the transfer student who immediately becomes an object of lust for Cher but is later revealed to be gay. His sexuality, though it drives some of the plot, is not the sole defining quality of his character — and the movie refreshingly frames it through Cher’s "bonehead" slow realization rather than any need for a dramatic coming-out monologue. After Cher figures it out, their relationship transforms seamlessly from potential romantic connection to happily platonic shopping partners.

This put Clueless among the ranks of several mid- and late-'90s movies and television shows that helped to normalize and deepen portrayals of LGBTQ characters, coming out (no pun intended) on the heels of MTV's The Real World season three, which featured out and HIV-positive Pedro Zamora, and paving the way for later shows like Ellen and Will & Grace.

4) There's nothing like a little Hollywood gloss to make the classics more palatable

Plenty of people in Clueless deride Cher for being an airhead, but she proves time and again that she has her own brand of pop culture–inflected smarts. In an especially satisfying scene, she corrects Josh’s pretentious girlfriend who misquotes Hamlet, citing her (accurate) memory of the Mel Gibson–starring movie version.

It’s a needed win for Cher, who's in a low patch at the time, but it's also a good reminder of Clueless's underpinnings as a modernized riff on Jane Austen's Emma. The movie’s target audience might not have spent weekends poring over the pages of 19th-century mannered comedies, but Clueless slapped a plaid skirt and a ‘90s sensibility on Austen's pointed societal commentary and made it appealing to new and younger generations. Heckerling's strategy paved the way for more teen-centric updates of classics both great (10 Things I Hate About You, Cruel Intentions) and not so much (the less said about O and She's the Man, the better).

5) Teenagers are practically their own species

I was a few years away from being a teenager in 1995, and, thus, many of the references in Clueless went completely over my head the first time I watched it. But the thing that stuck with me and that makes the movie resonate even now is the feeling of awe at what seemed like a new type of human being springing into brilliantly colored life on screen. These people had their own cars, their own cellphones (before that was really a thing), their own language even.

But what felt the most groundbreaking about Clueless was that it treated its characters' triumphs and woes with respect, as worthy issues to consider, even though they weren't saving the dregs of humanity from an oppressive government. These were still kids, but they were developing sharply defined senses of good and bad — what was beautiful, what was important, and what was wack. Clueless offered me my first inkling that someday, I might grow up to be a fully formed person, instead of constantly feeling like an awkward child utterly dependent on others.

Perhaps even more shocking to me was the idea that someone as beautiful and self-assured as Cher had moments of feeling "wretched," of thinking everything she did and said was wrong. As a painfully shy Canadian transplanted to suburban Texas and struggling to fit into my new world, Cher's struggles felt like a real epiphany.

These days what I remember of adolescence is the horrible things that happen to everyone’s bodies and personalities seemingly simultaneously — but watching Clueless reminds me of that fascinating, once-in-a-lifetime rush of self-discovery, of feeling out the edges of yourself and finding, to your surprise, that there actually were edges, delightful in their newness and uniqueness.

6) "Sporadic" means once in a while

I’ve never had to look it up since. Thanks, Clueless!

If you don't feel like dusting off your VHS tape, Clueless is available to stream on Netflix.