Towards The Mall: When CLUELESS Updated EMMA And Became An Instant Classic

More than just a 19th century tale in 20th century clothing.

Emma. (don't forget that period!) is hitting more theaters this week. Get your tickets here!

Many a piece of classic literature has one: a movie modernization that swaps the corsets and conventions of several centuries ago for the trials and tribulations of contemporary teenage life. The Taming of the Shrew has 10 Things I Hate About You. Les Liaisons dangereuses has Cruel Intentions. The Scarlet Letter has Easy A — and, as fans of Valley Girl’s update of Romeo and Juliet, O’s version of Othello and She’s All That’s take on Pygmalion all know, the list goes on. Twelfth Night has even received the treatment several times, via Just One of the Guys, She’s the Man and the Disney Channel’s Motorcrossed. But as stellar as some modern updates are (and as terrible as others prove, too), Clueless’ version of Emma is the genre’s queen bee.

That’s a fitting label for Amy Heckerling’s film, obviously. Cher Horowitz (Alicia Silverstone) is the epitome of Beverly Hills privilege — at home, in her swanky mansion; at the mall, buying more designer outfits for her motorized closet; and at school, where she fields compliments about her colour-coordinated ensembles and is firmly ensconced in the popular clique with her fellow Bettys and Baldwins. But Clueless doesn’t rise to the top just because it’s about a teen who already lives there. It’s a standout among modernized updates of classic literature because it does its job so smartly, thoroughly and engagingly. Indeed, it’s astonishing to think that, when Heckerling first started work on the project that would become Clueless, she wasn’t actually consciously using Emma as her template. That changed once she realized the parallels, and now Clueless is Emma’s best-known cinematic adaptation.

They might be separated by two hundred years, more than five thousand miles and a fondness for Luke Perry — that was teenage life in 1995, after all — but Emma’s narrative transforms into Clueless’ seamlessly. In the pages penned by Jane Austen 205 years ago, Emma Woodhouse is a young woman of means, standing, youthful hubris, and both social and financial security (“handsome, clever, and rich, with a comfortable home and a happy disposition,” as the book puts it), with the inhabitants of the fictional village of Highbury holding her in the utmost regard. She dotes on her widower father and runs their lavish household. Others flock to her, often to seek her guidance and approval. In fact, that’s how her chosen pastime — matchmaking — comes to flourish. In the town’s social strata, Emma ranks among the upper echelons, whether she’s helping her governess find love, advising her unsophisticated friend Harriet Smith to spurn lowly farmer Robert Martin for attractive vicar Philip Eton, pondering romance with the dashing Frank Churchill or bickering like a sibling with neighbour George Knightley.

In Clueless, Emma is reborn — figuratively, not literally — as 15-year-old Cher. At home and at Bronson Alcott High School, she’s held in the same high esteem as her literary predecessor; when she’s not reminding her high-strung lawyer dad (Dan Hedaya) to watch his cholesterol, she’s telling her classmates why assisting Haitians in need is the same as unexpectedly catering for extra guests at a garden party. And — first in an effort to improve one of her teachers’ lives so she can negotiate her way to better grades, then as a genuine way of helping others — she uses her school status to pursue the same hobby. When new student Tai (Brittany Murphy) arrives in class, Cher also gives her a makeover, discourages her from dating stoner skateboarder Travis (Breckin Meyer), and pushes her towards floppy-haired rich kid Elton (Jeremy Sisto). Later, Cher falls for the charms of the handsome Christian (Justin Walker), while also incessantly arguing with the college student ex-stepbrother, Josh (Paul Rudd), she wishes her family had lost in her dad’s divorce.

Summarized as per above, it all seems so easy. A few tweaks here, a reference to Marky Mark there, and Emma becomes Clueless. But Heckerling doesn’t just make cosmetic changes to Austen’s classic — she ponders it, interrogates it and truly understands what it means to bring a centuries-old text into a new era. The broad strokes might’ve been simple. If any modern situation lends itself to comparisons with the time of landed gentry, a formally stratified society, its inherent rituals and its dating practises, it’s high-school life. Thanks to Heckerling’s skill and care, however, Clueless overflows with thoughtful details that both link the film to its source material and contemplate its own thoroughly contemporary scenario.

Early in the film, Cher sits at her dining table, sharing a meal with her father and Josh. The topic of conversation is Josh’s legal studies, but it quickly becomes a discussion about Cher’s future plans — or meaningful lack thereof. Her dad says that she lacks direction. Cher disagrees, saying that she does, only for Josh to pipe in with: “towards the mall”. And, in the space of mere seconds, Heckerling savvily establishes Clueless’ skills as both an adaptation and a modernization. In Emma, the titular character’s eagerness to stay home with her father rather than find a husband and forge a separate life lingers over the entire narrative. Emma, like Cher, considers herself above the dating game, but to remain a woman of means, her only options are remaining with her father or marriage. In Clueless, Josh is mocking Cher with his mall comment, but the entire exchange stresses an important point: that Cher’s future path boasts plenty of possibilities, even if she just does just choose to fill it with shopping.

It’s these kinds of small details that give Clueless heft and depth; evidence that, in turning Emma’s experience into Cher’s, nothing has been overlooked. It’s one thing to merely transplant a familiar story into a new setting, but it’s another entirely to consider what the passing of time genuinely means for a character in that situation. Some instances remain superficial: in Emma, Emma paints a portrait of Harriet that Elton fawns over because he’s trying to attract Emma’s attention; in Clueless, Cher snaps a photo of Tai that Elton circa 1995 responds to in the same way and for the same reasons, for example. But when it matters, even in the most throwaway lines, Clueless continuously looks both back and forward. When Cher’s snarky nemesis Amber (Elisa Donovan) judges Tai on her outfit  — “she could be a farmer in those clothes,” she spits disapprovingly — Heckerling nods to the character’s Emma counterpart, Harriet, who wants to marry a farmer, while also noting that the savagery of judging someone based on perception has sadly withstood the test of time.

Heckerling’s film could’ve been totally buggin’ if she hadn’t taken to her task so meticulously and intelligently — all while unfurling her story within a realm that screams the opposite. There’s power in that choice, too, as well as in Clueless’ pop-littered soundtrack, glossy visual approach and upbeat, comic tone. The antics of wealthy, attractive high schoolers are easy to satirize and toy with but, for all her standing, Cher belongs to a group that’s easily and constantly trivialized. Teenage girls, no matter how well dressed and moneyed they are, have rarely been taken seriously. Nor have their interests, pursuits, hopes and dreams, either. In Austen’s time, the same applied to women generally — and unmarried women especially. Indeed, a modernized version of Emma wouldn’t work anywhere near as well outside the high school realm.

As if Clueless wasn’t going to become a classic itself. Any movie brave enough to paint Paul Rudd as the unattractive romantic alternative, even just initially, deserves to make a splash (see also: Baz Luhrmann’s Romeo + Juliet). So does a film that does much, much more than simply dress up a 19th-century tale in 20th-century clothing. Clueless is a fantastic version of Emma, but it’s also a fantastic musing on '90s teen life as well.