Cruel Intentions Was Weirdly Kinky in 1999 and Still Is Today

If the golden era of the high school movie was the 1980s, packed with John Hughes’ tales of wistful outsider girls and horny nerds, then mid-late ‘90s was the reprise. This was the era of Valley Girls (Clueless), the make-over movie (She’s All That, Never Been Kissed), and of course modern updates of classic literature (Ten Things I Hate About You, also Clueless). Cruel Intentions fits into this category and takes it to the next level. It’s a teen high school movie full of shagging and spitefulness which has genuine consequences and treats its characters like adults, while allowing them the naivety of youth. It’s 25 years old, and it’s still sexy as fuck.

Based on the novel Les Liaisons Dangereuses by Pierre Choderlos de Laclos’ which was filmed memorably as 1988’s Dangerous Liaisons, starring Glenn Close, John Malkovich and Michelle Pfeiffer, Cruel Intentions had wonderfully salacious material to work with but big shoes to fill.   

Taking the setting from pre-Revolution France to present day New York City, and translating French nobility into spoilt high school students, it’s the story of rich and influential step siblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe).  

The two are highly sexed, beautiful and corrupt. It’s the start of a new term, and Kathryn wants Sebastian to seduce freshman Cecile Caldwell (Selma Blair) as revenge on her ex, Court, who dumped Kathryn for Cecile. Meanwhile Sebastian has his sights set on Annette Hargrove (Reese Witherspoon), who has publicly stated she intends to wait for marriage before losing her virginity. Kathryn doesn’t believe he can do it. The two have a wager – if Sebastian can’t seduce Annette, Kathryn gets his car. If he does manage the seduction Kathryn will give him the one thing he can’t have…

“I’ll give you something you’ve been obsessing about ever since our parents got married,” says Kathryn. “I’ll fuck your brains out.”

It was subversive in the ‘90s and it remains so today. And if the idea of step siblings fucking seems a bit transgressive then Kathryn adds the cherry on top as Sebastian is leaving:

“You can put it anywhere…”

This is a film about sex and power, which is packed with taboo breaking scenes. Kathyrn is constantly coked up. Sebastian gets 15 year-old Cecile drunk and goes down on her without consent. Indeed Blair, who was 27 at the time, plays Cecile so young that the idea of her becoming Sebastian’s lover is incredibly uncomfortable. 

Speaking with Cosmopolitan, writer-director Roger Kumble stressed the importance of casting actors who were older than their characters.

“I remember having to ask all the actors coming in how old they were because that scene is, for lack of a better word, rape. So we were like, ‘All right, we’re gonna shoot this. It’s going to be dicey if we get away with it. But we can’t have an underage girl,’” he said.

Yet on the other hand, the snog between Cecile and Kathryn, when Kathyrn is teaching Cecile how to kiss, is one of the most famously erotic smooching scenes in cinema. Bit wrong, sure (not because they are both women – because Cecile is being manipulated by Kathryn), but sexy nonetheless. 

Films featuring drug use and underage sex among teens obviously exist. But rarely are they aspirational. No one wishes they were one of the kids from Kids. But Cruel Intentions makes it all seem impossibly glamorous and exciting. Nor is this a wholesome healthy exploration of young sexuality or a coming of age tale, unlike, for example, Sex Education on TV. Nor is it a deeply unsexy sex comedy, like the American Pie films. The closest film of the time was probably Wild Things with Neve Campbell and Denise Richards, but this was a consciously steamy erotic noir, as opposed to a glossy high school movie. The closest comparison of today would probably be Saltburn, for its focus on privileged beautiful young people with dubious morals, though Cruel Intentions doesn’t get involved with murders.

Kathryn makes the perfect baddie, and the casting was spot on. Gellar was of course best known for Buffy the Vampire Slayer on TV, then on film for I Know What You Did Last Summer, and Scream 2. As Buffy she’s a beautiful blonde cheerleader whose sideline as The Slayer casts her as not just the protector of Sunnydale against the creatures of The Hellmouth, but also as a champion of women and girls. She’s a savior and a role model for women and girls on screen and off, and her tragic love story with Angel was one of the most heart wrenching romances of the era. Unlike Kathryn, Buffy is dealt the ultimate punishment for expressing her sexuality – Angel’s curse (of having a soul) is lifted and the man she loves most in the world becomes her most vicious enemy. 

Kathryn wants to express her sexuality, but she is well aware the rules for women are not the same as those for men. 

“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,” she rails at Sebastian. “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.”

In this way she’s still a heroine and a role model, while also being something of a monster towards other women, making her the perfect reversal of Buffy. 

Then there’s Witherspoon, who was transformed into the perfect 1950s teenager in Pleasantville the year before. She’s the ideal of a wholesome blonde (the blonde vs. brunette trope is alive and well in Cruel Intentions), clever, beautiful and virginal. 

Witherspoon was already in a relationship with Phillippe before filming began – she would go on to marry him – and their chemistry was palpable, in a wholesome, true love kind of way (as opposed to with Kathryn which was pure sexuality.)

Philippe was probably best known for I Know What You Did Last Summer and was a fairly bog standard heart throb before Cruel Intentions but he really rose to the challenge. Following in the footsteps of John Malkovich as Valmont was no mean feat. Yet Phillippe’s lip-smackingly delicious as the arrogant womanizer tamed by Annette’s goodness who throws away the woman he loves for the sake of his reputation. It’s unfair, but he becomes the tragic hero by the end, killed in a fight orchestrated by Kathryn. He couldn’t have been allowed to live (Valmont is killed in the book too) but he has his (probably undeserved) redemption, while Kathryn has lost everything. She is ultimately punished by the two women she has manipulated – Sebastian gives Annette his journal which details Kathryn’s machinations and drug use, and Cecile distributes copies during Kathryn’s eulogy at Sebastian’s funeral – her precious reputation and status is ruined. After all the coercion and cruelty she has enacted, it’s ultimately her humiliation of Sebastian that is the nail in her coffin (as far as the film’s emotional arc is concerned). When Sebastian finally rejects Annette out of pride and comes to Kathryn for the spoils, she cuts him dead.

“You were very much in love with her. And you’re still in love with her. But it amused me to make you ashamed of it. You gave up on the first person you ever loved because I threatened your reputation. Don’t you get it? You’re just a toy, Sebastian. A little toy I like to play with. And now you’ve completely blown it with her. I think it’s the saddest thing I’ve ever heard,” she says. “So, I assume you’ve come here to make arrangements. But unfortunately, I don’t fuck losers.”

The sad thing is, she herself is humiliated. She rejects him not because he’s a loser, but because he rejected her. He was in love with Annette, and not Kathryn. Whether she ever loved him is questionable but she certainly didn’t like being spurned. Hell hath no fury etc.

Cruel games get you nowhere, the film says, as Annette drives off in Sebastian’s car, the one that was to be Kathryn’s. Good has triumphed over evil, Cecile has survived and can be with the music teacher she loves, Sebastian is dead and Kathryn ruined. Is that the ending we, the audience, are rooting for? It probably should be but didn’t we love being in Kathryn and Sebastian’s world? Cruel Intentions is best when it leans into its kinkiness and cruelty. It’s why the movie holds up and stands out 25 years on.

Cruel Intentions is available to stream on Prime Video.