Sarah Michelle Gellar in a scene from the film Cruel Intentions, 1999. (Photo credit: Columbia Pictures/Getty Images)
Aline Dolinh is Bitch Media’s 2019 Writing Fellow in Pop-Culture Criticism
I first consumed the film Jawbreaker in looping fragments nearly 16 years after its original release in 1999. It was the summer before my senior year of high school, and while I was by no means a social pariah, most of my time was devoted to the decidedly uncool pursuits of being a debate-camp counselor and aimlessly scrolling the internet inside air-conditioned rooms. I was a painfully self-conscious Vietnamese American girl who stood exactly five feet tall and took everything seriously, throwing myself into debate and theater and writing bad poetry with embarrassing fervor. Naturally, I was always trying to find opportunities to see myself in images of women who were everything I wasn’t.
I couldn’t get enough of the self-assured queen bees from high-school movies, whose glossy performances of teen girlhood gave me something literally impossible to strive toward—they were invariably white and played by beautiful twentysomethings. On one school-spirit day, my drama friends and I dressed up as characters from Heathers; despite being the only Asian girl in the group, I related much more to Heather Duke (Shannen Doherty)—the bulimic bookworm–turned–bescrunchied tyrant—than I did to cool outsider Veronica Sawyer (Winona Ryder). My own insecurities—the discomfort with my body, the envy toward female peers who already seemed impossibly successful, the constant craving for outside validation—were most acutely reflected not in the heroines who were able to rise above the fray, but in the mean girls who were too deeply mired in the sludge of adolescent uncertainty to escape.
This devotion led me to Jawbreaker, Darren Stein’s ultra-stylized black comedy centered on an elite clique of teenage girls who accidentally kill their benevolent leader during a misguided prank and then scramble to cover it up. Reviews of the film panned it as a slick rip-off of Heathers, which 10 years since its own release had found a vibrant afterlife in the form of grainy Tumblr gifs that presented the film’s caustic one-liners free of context. In Jawbreaker’s most iconic scene, the girls strut down a school hallway accompanied by the gleeful bombast of Imperial Teen’s “Yoo Hoo;” they’ve just left their newly dead best friend in a car trunk, but their skin-tight, candy-colored skirts and impeccably made-up faces reveal nothing as a crowd of their classmates scramble to clear a path.
In another scene, the clique’s cruelest member, Courtney Shayne (Rose McGowan), casually says, “I made you, and I’m God. That’s all you need to know,” as she leads a new acolyte, the formerly frumpy Fern Mayo (Judy Greer) across the cafeteria. Courtney is grooming Fern to replace tenderhearted Julie Freeman (Rebecca Gayheart), whose grief prompts her to break away from the clique entirely. Marcie Fox (Julie Benz), Courtney’s second-in-command, is largely portrayed as a vapid lapdog; but even she reveals hints of conscience when her doting single father (Jeff Conaway, aka Grease’s Kenickie, in a winking cameo) reminds her of the sweet, Tiffany-loving Girl Scout she once was. By contrast, Courtney is not a particularly nuanced character. She’s an unrepentantly nasty bully who attempts to cover up her friend’s death by framing a random, innocent man. Her parents, unlike Marcie and Julie’s, are entirely absent from her life, as if she materialized fully-formed from the void as—in Fern’s words—“Satan in heels.”
Yet Courtney’s shameless confidence and sexual charisma felt subversive to me: What other teen-movie antagonist was bossily compelling enough to talk a beefcake jock into fellating a popsicle as foreplay? Her motivation has nothing to do with the heterosexual rivalry that animated the queen bees who preceded her in teen dramas; she values men only transactionally, dismissing her would-be prom king as “a yearbook photo…a piece of nostalgia that won’t stand the test of time,” even as she acknowledges his crucial status in the high-school social hierarchy. There’s no hidden trauma that explains or rationalizes her cruelty; she’s simply a force of nature.
But there are also moments when Courtney’s surreal persona hits real nerves. While training Fern in the art of mean-girling, for instance, she explains why their clique don’t eat at lunch: “We’re not stupid. We eat, and we eat well. We just don’t eat in public…We don’t want people judging us by what we eat. It gives them ammo. The only ones with ammo are us.” To be sure, Courtney has little sympathy for the insecurities of her female peers—she scorns anorexia as a dorky weakness “reserved for the Karen Carpenter table”—but within the absurdity of this monologue (“the mere act of eating invokes thoughts of digestion, flatulation, defecation … even, shall we say, complexion defection”) is a genuinely bleak assessment of how the cult of constant self-improvement wreaks havoc on young women’s psyches. Courtney seemed to understand that simply being a teenage girl was synonymous with hypervigilant performance.
These films reflect a cultural tradition that stretches back to early modern witch hunts, imagining teenage girls as endowed with a capacity for evil that their male peers are too normal to possess.
1999 was a particularly rich year for cinematic representations of teenage girldom; films like 10 Things I Hate About You, Drive Me Crazy, and She’s All That were earnest teen romantic comedies that are now considered foundational in their own right. But Jawbreaker and the equally dark Cruel Intentions, released within weeks of each other, stand out for their sheer cynicism and brazen treatment of sexuality.
Cruel Intentions was an adaptation of the 18th-century epistolary novel Les Liaisons Dangereuses, a story of erotic intrigue amidst the French aristocracy that had already seen high-profile screen adaptations with 1988’s Dangerous Liaisons and 1989’s Valmont). Cruel Intentions transplanted the plot into the world of wealthy, dissolute Manhattan teens, kicking off with a bet between conniving step-siblings Sebastian Valmont (Ryan Phillippe) and Kathryn Merteuil (Sarah Michelle Gellar). Sebastian is determined to seduce virginal Annette Hargrove (Reese Witherspoon), who has proclaimed her intention to save herself for marriage, and Kathryn is confident that he can’t do it. If she wins, she gets his vintage Jaguar; if he wins, he gets to have sex with her.
These teens, clearly, are not meant to be role models: Kathryn masquerades as a God-fearing model student, but has no qualms about destroying the life of guileless Cecile Caldwell (Selma Blair) to get revenge by proxy on a boyfriend who has unceremoniously dumped her. And Sebastian’s charm barely conceals a pattern of harassment and exploitation: He nonconsensually posts nude pictures of a conquest online, blackmails a closeted classmate, and manipulates Cecile into sex.
Kathryn is at least aware of how her destructive behavior is informed by the unfairness of her circumstances, rightly venting to her step-brother that even the uppermost echelons of privilege harbors a double standard for male and female sexuality. (“God forbid I exude confidence and enjoy sex. Do you think I relish the fact that I have to act like Mary Sunshine 24/7 so I can be considered a lady? I’m the Marcia fucking Brady of the Upper East Side, and sometimes I want to kill myself.”
But it’s Sebastian who ultimately gets redemption, proving his love for Annette in the film’s soap-operatic finale when he throws himself in front of a car to save her life. All his transgressions are seemingly absolved in death, and Kathryn’s duplicity is ultimately framed as a greater sin than his outright predation. Both Cruel Intentions and Jawbreaker have endings clearly meant to offer satisfying comeuppance. Kathryn’s vicious scheming (and her cocaine habit) is exposed at Sebastian’s funeral when Cecile distributes his photocopied diary to all their classmates, effectively allowing him the last word. Jawbreaker’s Courtney is disgraced (and most likely arrested) when her former deputies broadcast her crimes to the school during prom, enduring a figurative stoning-by-corsage and the further humiliation of a Polaroid of her mascara-streaked mug.
In her 2008 book Maiden USA: Girl Icons Come of Age, Kathleen Sweeney observes that these two films specifically “played into an odd simultaneity of adult nightmares about their daughters’ secret lives and soft-core fantasies about their precocious level of sexual activity […] By the end of these movies the Queen Bees are subjected to group ridicule and scapegoating with a ferocity that mirrors their own scheming at the beginning.” It’s true, of course, that Kathryn and Courtney’s abilities to manipulate are clearly inextricable from their wealth and whiteness. But neither film indicts privilege wholesale; both are simultaneously obsessed with and repulsed by their sexually assertive, intensely self-possessed female villains. Their narratives reflect a cultural tradition that stretches back to early modern witch hunts, imagining teenage girls as endowed with a capacity for evil that their male peers are too normal to possess. For the longest time, I believed that was the same thing as power.
Cruel Intentions and Jawbreaker seem almost quaint in their mean-spiritedness now that the teen-movie genre has shifted toward increasingly down-to-earth narratives that feature more diverse casts and seem to possess a greater sense of responsibility to the demographics that they’re representing. The sweetly inoffensive coming-out story of 2018’s Love, Simon—the first major American studio film to focus on a gay teenage romance—literally begins by reassuring its audience “I’m just like you!” Likewise, Netflix’s recent original film To All the Boys I’ve Loved Before owes much of its viral success to its portrayal of a charming, ultra-relatable Asian American Everygirl.
But in pushing the limits of teen-movie drama, Jawbreaker and Cruel Intentions were a gateway to a new generation of stories that imbued the adolescent alpha bitch with greater humanity. The cultishly beloved Mean Girls granted its tyrannical queen bee Regina George a redemption arc that rerouted her girl-on-girl aggression into lacrosse. Ten years after the release of the horror flop Jennifer’s Body, there’s been a reconsideration of how marketing the film for a teen-male gaze shortchanged its confrontation of female stereotypres. Late-aughts teen soaps Gossip Girl and Pretty Little Liars were anchored by the emotional development of Machiavellian mean girls who were put through the wringer in increasingly absurd ways but nevertheless grew into successful, fully-realized adults. On current hits Riverdale and The Chilling Adventures of Sabrina, teenage ice queens fall in love, wrestle with familial strife, and form grudging bonds with the nice-girl protagonists without having to relinquish their power.
It’s also true that these shows’ politics are often vastly flawed. Pretty Little Liars and Gossip Girl both concluded by marrying at least one of their leading ladies to predatory, exploitative men. They’re also invested in exalting white femininity as a default state; Gossip Girl’s nonwhite characters are mostly lackeys and wannabes, and Sabrina’s Prudence Night (Tati Gabrielle) is initially characterized as a “racist” against mortals and forced to endure a questionable hanging scene at the hands of Sabrina (Kiernan Shipka) before she’s revealed to have real complexity. Yet because teen dramas like these shaped adolescent psyches like mine, I’m grateful to see the number of critics who take even their contradictory and troubling themes and messages seriously.
The internet and social media have fundamentally transformed young women’s ability to be critics as well as consumers of media. My own feminist education was informed simply by other young women circulating images of pop-culture figures they adored—and maybe saw themselves reflected in, even if they couldn’t articulate why. Part of the joy of reblogging Tumblr gif sets of Courtney and Kathryn’s best lines was reading commentary from others, often in the form of affirmations like “#goals” and “#MOOD” and “#deserved better!” And that joy was paired with the question of why characters who were undeniably the coolest, wittiest, and most magnetic figures onscreen were also the ones who never got to win in the end.
From there, I began questioning why I gravitated toward such rarefied and overwhelmingly white representations of girlhood to begin with. Representations of teenage girls didn’t became more progressive overnight; I didn’t magically become a more confident person. But I gained a frame of reference for these feelings as I kept seeking out images of girls who ate and fucked and sweat and bled without shame, and the world I sought to see myself in simply grew larger than the sphere of high-school movies. A scroll through the pages tagged #me and #same of the Tumblr blog I started when I was 13 reveals an eclectic archive of the fictional girls with whom I identified: Along with Heather and Courtney and Kathryn, there was Azula (Grey Griffin) from Avatar: The Last Airbender, Lane Kim (Keiko Agena) and Paris Geller (Liza Weil) from Gilmore Girls, and the titular heroines of Anne of Green Gables, Sailor Moon, and Veronica Mars, among countless others.
The most iconic antiheroines of 1999 might have killed a specific type of teen dream, but they paved the way for a messier, more lifelike set of formidable young women to come of age in their place. I’ll always owe them the realization that even my heart’s most embarrassing longings—to be unquestionably pretty, to be envied rather than assimilated, to be a luminous object of desire—were impulses that didn’t exist in a vacuum. They taught me that the urge to take those desires seriously didn’t make me shallow or stupid or worthy of shame; it was just part of navigating the world within a young woman’s body, a form that sometimes feels like a strange costume I am still learning how to love.
