It’s been 20 years since Cruel Intentions strutted into theaters, awing ’90s teens with its salacious tale of sex, lies, and rosary/cocaine-spoons. I still remember the illicit thrill of watching bad boy Sebastian (Ryan Phillippe) incestuously flirt with his sneering stepsister Kathryn (Sarah Michelle Gellar). So when this gleefully trashy adaptation of Pierre Choderlos de Laclos’ Les Liaisons dangereuses returned to theaters for an anniversary revival release, I was giddy to revisit its titillating world of ’90s fashion, fantasy, and f*ckery. Does it hold up?
Adapted and directed by Roger Kumble, Cruel Intentions was part of the trend of transforming classic novels/plays into hot properties targeted at the teen demographic, like Clueless, Baz Luhrmann’s Romeo + Juliet, and 10 Things I Hate About You. The 18th-century French novel was transported to contemporary Manhattan, where its aristocrats became privileged socialites who possessed massive apartments overlooking Central Park, classic cars, and zero parental oversight. Hot off the teen-slasher I Know What You Did Last Summer and steamy drama 54, ingedude Phillippe brought his pouty lip and curly locks to the lead role of Sebastian, a playboy who is as conniving as he is bored, a dangerous combination. His first outlandish act is exacting revenge on his overpriced therapist (Swoosie Kurtz with a sharp cameo) by slut-shaming and cyber-bullying her daughter (a pre-American Pie Tara Reid). Then, it was played for laughs; it’s hard to imagine it playing that way today.
Of course, Sebastian is supposed to be a cad. Bored of bedding the easily conned girls of Manhattan, he sets his sights on a harder conquest: new-to-town Annette Hargrove (post-Pleasantville Reese Witherspoon), who became the poster girl for virginity thanks to her Seventeen op-ed “Why I Plan To Wait.” He makes a bet with his surly but sexy stepsister, that if he snatches the good girl’s virginity, incestuous sodomy is on!
Most of his bad behavior is meant to give us a vicarious thrill. His blackmailing of a closeted and crass jock is played for lurid shock value, aided by a bleach-blonde gay stereotype (Joshua Jackson, RIP) who quips, “the man’s got a mouth like a HOOVER!” His drugging and sexual coercion of naïve Cecile (Selma Blair) is played for comic relief, complete with goofy face-making and pratfalls. There’s an implication that these beautiful, entitled assholes have it coming for being dumb while rich. But our sympathies are meant to shift when we meet wealthy yet smart Annette. To seduce her, Sebastian begins with negging, then employs blackmail, outright lies, and the lure of his bare backside. Her refusal to be easily conned by him is intended to impress us, and thereby she’s not deserving of his abuse. Even Sebastian is charmed by her. And we’re meant to swoon and buy into his redemption arc. 20 years later their romance is much harder to root for.
Part of it is that even Sebastian’s milder trespasses—like negging and casually using words like “b*tch” and “f*g”—have evolved into big red flags. And it’s hard to shrug off the opening act of such senseless slut-shaming. But more than that, in the wake of Me Too, his personal low point doesn’t feel low enough to earn his redemption. It feels like those creeps who get called out for their misconduct and are gone from public life for a brief period, then think an apology is all they need to prove they’ve changed. Despite falling for Annette, Sebastian willfully breaks her heart. He’s sad and genuinely remorseful for a sequence or two, and then he dies by throwing Annette out of the way of oncoming traffic. Our sympathies are meant to go to heroic Sebastian because he died after being a good guy for a whole four seconds! Sure, that doesn’t make up for how he ruined the life of the therapist’s daughter, shamed a fearful gay teen, or snatched the agency from Cecille. But hey, remember how sad he looked when “Color Blind” played?
While Sebastian’s story doesn’t age well, there’s something still deeply delicious and relevant about Kathryn’s story. A couple seasons into Buffy The Vampire Slayer, Gellar was making her play for movies with niche-busting roles. In Scream 2 and I Know What You Did Last Summer, she played sorority girls and beauty queens that had no hope of kicking butt against the killers out to get them. Then with Cruel intentions, she got to cut loose, cranking Buffy snark up to sneering diva levels. Twenty years later, you can see the charm that made Witherspoon a star, appreciate the comedic splendor Blair brought to an underwritten role, and recognize that Phillippe was handsome and is also in this movie. But this movie belongs to Gellar, who didn’t just sink her teeth into the role of this poor little rich girl, she ripped out its jugular and made a bloody, marvelous meal of it.
To the grown-ups of New York, Kathryn is a picture-perfect Upper East Side princess. She’s got great grades, waxes poetic about her trust in God, and maintains a perfectly pleasant appearance. But as soon as the lone parent in this film, Bunny Caldwell (the spectacular Christine Baranski), is out of the foyer, Kathryn transforms. Her pert tone sinks to a snarling purr. Her crisp physicality slinks into curves and caresses. This queen bee is a queen bitch, who plays her friends and family as pawns to her own ends. Not so much out of boredom, as Sebastian does, but because she resents the impossible double-role she’s been given.
In a scathing monologue, Kathryn rejects Sebastian’s hypocritical scorn for “destroying an innocent girl.” She responds, “Eat me, Sebastian! It’s okay for guys like you and Court to fuck everyone. But when I do it, I get dumped for innocent little twits like Cecile. 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. So there’s your psychoanalysis, Dr. Freud.”
Kathryn and Sebastian are both monsters born of privilege. Their wealth and status protect them from the consequences of most of their nefarious actions. However, there is a double-standard at play that Kathryn is acutely aware of. Sebastian’s sex drive and resulting bad behavior is written off as boys will be boys. Hers gets her dumped by Court, scolded by Sebastian, and potentially slut-shamed by the whole of her social circles. So she has to carefully maintain a flawless, modest façade. It’s not boredom that fuels Kathryn, it’s the return of the repressed.
Her desire to be herself twists inside her then lashes out through her sharp intellect and rage at those who are allowed the chance to be less-than-perfect. Which makes the end, where Kathryn is painted as the Big Bad, feel like Kumble missed the point of the monologue he wrote. As “Bittersweet Symphony” blares, Kathryn cries and we’re meant to feel all is right in this posh, pretty world. But will the release of Sebastian’s journals change anything but the pecking order? Won’t Cecile and Annette be slut-shamed alongside Kathryn? Don’t think about that, the movie seems to croon as it cuts to Annette, carefree and driving off in Sebastian’s car.
It’s a strange thing to revisit a movie you clung to so desperately in your youth. I felt like I was watching Cruel Intentions alongside my 16-year-old self, a small-town girl who fantasized about living in New York amid the fashion and thrills. I want to scold her for thinking Sebastian is hot, despite his bad boyfriend behavior. I want to educate her on the Male Gaze of the faux-lesbian lip lock. I want to scream at her about consent and coercion. Because I also remember vividly looking to these movies to tell me what the wider world would be like. But even amid my cringing, I still feel the flush of her excitement over that kiss. Sure, it was intended for boys to thrill over, but this baby-bi did too. I still feel the fondness for the fashion, from strappy camisoles to transparent metallic blouses. I still sing along to Placebo, Counting Crows, and The Cardigans as their hits pop into the soundtrack. And here, side-by-side, I get to keep to visions of this movie. The one I had at 16, where it was edgy and exhilarating. And the one at 36, where I cringe over the problematic bits, while treasuring the fashion, the transgressions, and the wicked fun of Cruel Intentions.
Header Image Source: Sony