Why, 25 Years Later, ‘Clueless’ (1995) Remains Our Smartest Jane Austen Adaptation

When Jane Austen began work on her 1815 novel, Emma, she predicted that her heroine would be one “whom no one but myself will much like.” It’s true that Emma Woodhouse, being “handsome, clever, and rich, with a comfortable home and a happy disposition,” moving through her provincial life “with very little to distress or vex her,” enjoys an annoyingly charmed existence. It’s one that allows her to believe that she is both for the people and irretrievably above them, an echo-chamber in which her own worldview is reinforced again and again, not because it is correct or just, but because it is hers, the young mistress of a sprawling country estate. Emma’s life is charmed because it is blissfully uncomplicated, and because the people around her—limited by the constraints of class and polite society—take measured steps to keep it that way. 

Alicia Silverstone as Cher proudly displaying bags from designer brands.
Alicia Silverstone as Cher Horowitz. Image courtesy of Paramount Home Entertainment.

Emma’s life isn’t quite perfect, of course: she’s lost her primary mother figure after her governess’s recent marriage, and she seems destined to spend her most eligible years caring for her slightly agoraphobic, hypochondriac father. But Emma has the astounding, maddening skill—as well as the enviable and almost unheard-of financial stability—of treating these deeply consequential truths as nothing more than mere footnotes in an otherwise full and well-rounded life. She is unbothered and undeterred, sometimes to a fault. Her self-assuredness and resilience are as infuriating as they are inspiring, and therein lies Austen’s brilliance. She did, as she predicted, create an unlikeable character: Emma is spoiled, rich, presumptuous, and selfish. But the things that make Emma unlikable are also the things that make her captivating; she is spoiled and rich, but only because her father, forever changed by his beloved wife’s death, has essentially left Emma to raise herself; she is presumptuous, but only because her singular lifestyle—unmarried mistress of a wealthy estate and without societal peer—has allowed her to live a life without deference, where no one can be her equal simply because they must answer to people other than themselves; and she is selfish, but only because acts of charity and matchmaking are her chosen forms of entertainment. Emma’s kind of thoughtless thoughtfulness is unique to her, but it is also a direct result of her circumstances. Austen’s critique, then, does not land squarely on Emma’s shoulders (although she undoubtedly shares in the blame for her less charitable actions) but on those of the society that created her and then left her unchecked. Emma is many things—a comedy of errors, a romance, a coming-of-age story—but it is first and foremost a catalog and critique of the foolishness fostered and encouraged by wealth—empathetic and caring, but a critique nonetheless.

Many film and television adaptations have tried to recreate Austen’s insightful tale of womanhood and wealth, and a few have succeeded—the BBC’s 2009 four-part miniseries, starring Romola Garai and Jonny Lee Miller, comes to mind as one of the most faithful period adaptations—but the smartest, most nuanced take on Emma Woodhouse’s blissful ignorance is not an intricate, painstakingly-researched period piece: it is a romantic comedy set in a high school in the decidedly non-provincial hamlet of Beverly Hills. Amy Heckerling’s 1995 instant-classic Clueless understands perfectly what Jane Austen so plainly laid out, and what other adaptations, including Autumn de Wilde’s recent Emma., seem to forget: that Emma—or in this case, Cher Horowitz, played to Valley Girl perfection by Alicia Silverstone—is not mean-spirited, nor intentionally haughty, nor willfully ignorant. She simply does not quite get it, whatever it may be. She is, in a word, clueless. Cher, like Emma before her, is a product of her circumstances, a girl who can be impossibly herself simply because no one ever tried to stop her. Clueless is not just a title: it is a label, a jest, and a thesis all at once, a one-word summary of Heckerling’s brilliant insights into the lifestyles of the young, rich and—to keep it PC—perceptionally challenged.

Cher and Dionne standing near the teacher mailboxes at school, carrying out their plan to make a romantic match between two teachers.
Cher and her best friend Dionne (Stacey Dash). Image courtesy of Paramount Home Entertainment.

In a film chock-full of quotable lines and memorable moments—the yellow plaid ensemble! “As if!” The near-death experience on the freeway! “It does not say RSVP on the Statue of Liberty!” every single thing Paul Rudd does!—Heckerling’s greatest accomplishment is her treatment of Cher. She is introduced frolicking through the streets and boutiques of Beverly Hills with her improbably beautiful friends as “Kids in America” plays joyfully and almost ironically in the background—these are not exactly your average “dirty town,” “suburbia sprawling” teenagers. But Cher seems aware of her unique position in life, laughing knowingly over the montage: “So, O.K., you’re probably going, ‘Is this, like, a Noxzema commercial or what?’” It feels like an acknowledgement of the fact that her life is inconceivably picturesque—until, of course, she continues: “But seriously,” she insists, “I actually have a way normal life for a teenage girl. I mean, I get up, I brush my teeth, and I pick out my school clothes.” This she says while selecting her outfit on a closet app thirteen years before apps as we know them became a thing, but don’t worry, it’s not a big deal.

To the untrained eye, it seems like Heckerling is ridiculing Cher’s uniquely adolescent lack of irony, and it’s true that she is. But the point is not that Cher is simply unaware of the gap between her Instagram influencer life and her just-a-girl self-perception—it’s that she literally cannot see it. She is blinded by the consistency of her own experiences, and stubborn enough to make anyone and anything outside of her own perception of life fall in line.

So it doesn’t matter that, in many ways, Cher is an anomaly. It doesn’t matter that she is an exceptionally wealthy teenager who lives by her own rules, not out of age-standard rebellion but because her loving, if vaguely absentee father simply does not have the time to create any. It doesn’t matter that she’s cultivated a worldview made of rigid categories, in which “no respectable girl actually dates” the “loadies” who hang on the grassy knoll, or where the best way to get a potential beau’s attention is sending yourself flowers and candy and doing “anything to draw attention to your mouth.” Because of the way Cher grew up, she cannot see her life as anything but standard, and for that she is actually deeply and hilariously normal. Heckerling understands that Cher is a teenage girl, caught up in her own life. She’s incredibly conscious of appearances and the way things look, but at the same time, she is always going to be the author of her own story. What the audience thinks, what her peers think, ultimately doesn’t matter—Heckerling knows that if it doesn’t line up with Cher’s self-perception, then it’s not much worth entertaining.

Amy Heckerling directs Alicia Silverstone on set.
Amy Heckerling and Alicia Silverstone on set. Image courtesy of Paramount Home Entertainment.

What Heckerling also understands about Emma—and Cher in turn—is that this blind self-belief is not malicious, or self-important, or even intentional. Cher, for all of her designer labels and convictions about The Way Things Are, lives a small life. She’s sheltered as a function of her wealth; she doesn’t know the world outside Beverly Hills because she’s never needed to. She advises Brittany Murphy’s wonderfully pure-hearted Tai, citing the fact that she is “someone older,” but in truth, she is also still learning. The problem is that Cher—fueled by the strength of her convictions and, in Austen’s words, “the power of having rather too much her own way”—is not particularly good at learning. Think of her report card negotiation: it’s proof that Cher is smart and perceptive when she wants to be, but she fails to apply that intelligence to her actual education. It’s not that she refuses to know things or is incapable of knowing them, it’s that her life has never required her to have the discipline to truly learn them. 

This lack of discipline expresses itself not in blatant ignorance but in subtle verbal slips. Cher makes a passionate and empathetic argument for sheltering refugees, but calls them “Hate-i-ans.” (This mispronunciation was actually a mistake on Silverstone’s part, but Heckerling so enjoyed the mistake that she let it slide.) When the smooth and suave Christian Stovitz (Justin Walker) asks her if she likes Billie Holiday, Cher answers: “I love him.” As she and her best friend Dionne (Stacey Dash) plot to make a love match for their romantically-challenged teachers (Wallace Shawn and Twink Caplan), she quotes Shakespeare’s eighteenth sonnet in a love note. Dionne is impressed, but Cher gives credit where credit is due: “Duh! It’s, like, a famous quote.” “From where?” “Cliff’s Notes.” It’s a wonderfully modern take on Emma’s particular brand of confidence: like Emma, Cher does know things, but rarely does she know them all the way. It’s why she can see that Tai is in need of a friend as she starts at a new school, but can’t see that making Tai a miniature Cher is not a sustainable expression of that friendship. It’s why—in a brilliant callback to Emma—she can see that Elton (Jeremy Sisto) asking for a picture of Tai is an obvious romantic gesture, but she can’t quite see towards whom. Cher has never needed to follow her impulsive conclusions through to their logical ends, but as we meet her, we can see that truth rapidly deteriorating. Cher’s naiveté is part and parcel of the life that she been allowed to lead—but worlds expand. The way things are is not always the way they will be. You meet a girl, you make mistakes, you go out for some retail therapy, and you realize: “I was just totally clueless.” 

Cher with a confused face, riding in her friend's car.
Cher doing some Realizing. Image courtesy of Paramount Home Entertainment.

Cher’s meddling matchmaking, the party where Josh mercifully dances with Tai, Cher’s aversion to dating high school boys—all of these are pitch-perfect spins on Austen’s original manuscript, a delight to watch even when you haven’t read the book and even more so when you have. But what makes Heckerling’s adaptation so instantly classic is not the outfits, nor the quotes, nor even the fact that Josh’s cherubic face makes us forget that he’s Cher’s ex-stepbrother: it’s this astute understanding of the improbable trials of wealth. When 20th Century Fox approached her to make something about “the in-crowd,” Heckerling agreed only on the condition that she could make fun of them—and she did. But she did it in such a way that acknowledges that Cher is both the hero and villain of her own story. She is privileged, stubborn, and, yes, a little ditzy, but she is also open-minded and in search of self-improvement, and in the end, that is what makes Cher memorable, and Emma endlessly adaptable. Clueless like its predecessor, balances its moments of empathy perfectly with its cutting satire. It doesn’t judge Cher, but it doesn’t let her get away with her antics either. It knows that being a virgin that can’t drive is not a permanent condition, and that even the most unlikeable heroines can redeem themselves if given a proper push. In a sea of Emma adaptations, only Heckerling has followed Austen’s example with wild success: she took the room left to make Cher insufferable and superior and malicious and instead, gave her clueless heroine the space to hop in a car, meet a guy, and, well, get a clue.