Why the complexity of Kathryn in Cruel Intentions still matters in 2019

The iconic ’90s film Cruel Intentions turned 20 years old on March 5th, 2019. Here, HG contributor Veronica Walsingham reflects on how the purity culture of the ’90s made Kathryn Merteuil a rebellious heroine for teen girls and a problematic character at the same time.

To say that Sarah Michelle Gellar’s Kathryn Merteuil is actually the hero of Cruel Intentions is, I know, a rather bold statement. This is a character who schemes to destroy the reputation of one woman, makes a bet about the virginity of yet another woman, and even tells her step-brother that he can “put it [his penis] anywhere.” She is a high school student who sports a crucifix necklace brimming with cocaine.

This is, of course, not the typical recipe for a film’s hero, but Cruel Intentions is, of course, not the typical teen film.

It is a moody, R-rated film following a set of vicious teenagers with wicked sexual appetites that parades itself as a love story of sorts—albeit a love story that starts with a bet about a woman’s virginity, but a love story between Sebastian (Ryan Phillippe) and Annette (Reese Witherspoon) nonetheless. At its core though, Cruel Intentions is a film that is most interested in cynically examining the expectations placed upon young women in our society. And it’s by this measure of the film that Kathryn, the character most frustrated with the misogynistic culture in which she lives, is the film’s hero to me.

To understand Cruel Intentions and Kathryn Merteuil, context is key. It was 1999. Just one year prior, Bill Clinton’s affair with Monica Lewinsky had made headlines. Rather than sparking nuanced discussions about workplace relations, especially between those with power imbalances and at different stages in their careers, the public reaction was mostly criticisms of Lewinsky’s appearance. Lewinsky, a 20-something White House intern, was essentially cast into the role of the wanton villain, rather than the victim. This presidential sexual scandal only helped fuel the rise of purity culture, which emphasizes the importance of remaining a virgin until marriage. But it can also instill sexual shame, especially in young girls who are taught that they are responsible for upholding virginity in their relationships.

In the ’90s, purity culture grew legs when young pop stars like Jessica Simpson and Britney Spears spoke publicly about their desire to stay virgins until marriage. A younger wave of pop stars—the Jonas Brothers, Demi Lovato, and Hilary Duff—would also follow in their footsteps. This only made girlhood even more confusing for those growing up in the early ‘00s. Girls were largely taught abstinence-based sex education in school while their midriff-baring pop star icons professed plans to save themselves for marriage and one of the most talked about images in pop culture was a supposed stain on a young intern’s dress.

To have released a film like Cruel Intentions, showcasing the devious sexual escapades of teenagers in 1999 was…well, it seems like it was exactly what teenagers of the time wanted to see, despite the film’s R-rating. The film tapped into the dark underbelly of teenage life, showing how weighty expectations and boredom can lead to social aggression. And if this film was what teenagers needed, Kathryn was who teenage girls needed.

Girls needed to see a female character who raged about the double standard of men getting to sleep with whomever they want while sexually active women get dumped for “innocent, little twits like Cecile.”

In the same breath, Kathryn goes on to say, “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 f*cking Brady of the Upper East Side, and sometimes I want to kill myself.”

The film’s narrative itself even highlights this double standard. Both Kathryn and Sebastian are sexually manipulative, yet the narrative softens towards Sebastian, giving him a redemption arc through his self growth. Yet the film only grows colder towards Kathryn, who seems to even shoulder some responsibility for Sebastian’s death.

The film literally begins with Sebastian posting nude photographs of one of his “conquests” to the internet without her consent—because her mother is his therapist and he thinks she’s overcharging him—yet the film wants us to root for this guy in the end?

Say what you will of Kathryn sexually manipulating her step-brother, but she was certainly spot on about the double standard surrounding men and women’s sexuality.

In terms of other female characters, there’s Annette and Cecile (Selma Blair), both showcasing innocence and virginity. Annette says things like, “People shouldn’t experience the act of love until they are in love, and I don’t think people our age are mature enough to experience those kinds of emotions.” And Cecile’s sexual cluelessness and overall naivety get most of the laughs throughout the film. Still, I’d argue that while, yes, Annette and Cecile were of much higher moral integrity, Kathryn’s frankness made her the most likable. Annette and Cecile seem to have accepted unfair societal expectations and smiled, while Kathryn smiles in sexism’s face only to hold up her middle finger behind its back.

The fanfare for Cruel Intentions’s 20th anniversary wasn’t all that surprising, given there’s been very few films like it since.

Culture’s pendulum has swung away from mean girl characters towards kinder stories of inclusiveness. There’s also the fact that this version of New York City—with its absurd excess, wealth, and access—is no longer depicted that often. Since the recession, the N.Y.C. of Cruel Intentions, Gossip Girl, and Sex and the City was traded in for Broad City’s grittier, financially worrisome depiction of city life. In this way, both Cruel Intentions and Kathryn exist as artifacts of a different time, ever preserved in 97 minutes of film.

To some, calling Kathryn a hero may be a step too far in congratulating her brand of calculating behavior. But young women coming into their own sexuality so rarely, if ever, get to see female characters say they “exude confidence and enjoy sex.” That perspective can be important for them to see  on the screen, especially at a time when they were learning to be ashamed of their sexuality from so many different parts of culture. Though, of course, Kathryn should have put her anger toward misogyny to better use than scheming against other women.

To me, Kathryn remains a tragic film character. She is a woman conforming to a culture that she despises, and in turn, despising herself for conforming. Her deep desire to succeed within this culture—one that tells her not to be too slutty, but not to be too prudish—can perhaps best be summed up with the first line she utters: “I’ll do my best.”

“Doing my best” in this society was a sentiment I also knew far too well in 1999, and maybe still know too well in 2019.