Cruel Intentions (1999) is the third film adaptation of the French novel Les Liaisons dangereuses by Pierre Choderlos de Laclos. The original story takes place in 18th century France and revolves around two romantic rivals who revel in manipulating others using sex, secrets and anything else at their disposal. Their motivations vary from revenge to sheer entertainment. Written and directed by Richard Kumble, Cruel Intentions is a modern take on the original story. The film takes place among the upper echelon of New York society, and the story’s two antagonists, Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe) are students at an exclusive private prep school.
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When it comes to teen films in the ’90s, Cruel Intentions steps away from the sophomoric humor of other movies in the genre like Can’tHardly Wait, American Pie, She’s All That and 10 Things I Hate About You by veering into much darker and sexually charged territory. Here’s a list of the 10 most shocking scenes in Cruel Intentions, ranked.
The Therapist’s Daughter
Sebastian’s therapy session reveals a young man born of privilege who is appeasing counselors and parents, not exploring the motivations behind his actions. His contempt for his female therapist, Dr. Greenbaum (Swoosie Kurtz), is thinly-veiled, and his inappropriate sexual overtures are meant to make her uncomfortable. The true depth of Sebastian’s depravity becomes apparent when Dr. Greenbaum’s daughter, Marci (Tara Reid), reveals he’s responsible for posting nude photos of her on the internet.
Sebastian’s actions are meant to expose Dr. Greenbaum as a fraud. She’s a supposed expert, but her parenting skills are lacking. She either can’t see through Sebastian’s act or doesn’t care. Either way, it’s hard to muster up sympathy for her. Sebastian is willing to blow up Marci’s life to prove he can outwit his hack of a shrink.
The Bet
It’s immediately apparent that even though there’s a sibling rivalry at play between Kathryn and Sebastian, they don’t have a familial relationship. They are only related by law and not blood, but that doesn’t diminish the inappropriateness of their sexual attraction and flirtation. The bet they make regarding Sebastian’s ability to seduce the new headmaster’s daughter, Annette Hargrove (Reese Witherspoon), emphasizes the incestual nature of their bond. The only thing Kathryn has to barter with that entices Sebastian is her sexuality, and the promise of letting him have sex with her whenever he wants should he win.
Going To First Base
An inexperienced Cecile Caldwell (Selma Blair) gets her first taste of a sexual awakening during a picnic in Central Park with Kathryn. This scene hasn’t retained the shock value it had when the movie was first released, but at the time, the kiss between Kathryn and Cecile was a big deal.
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Sarah Michelle Gellar was famous for playing Buffy the Vampire Slayer, and this moment blew her on-screen persona out of the water. The lip lock remains erotic made even more famous by the thin line of saliva connecting their lips once they break contact
Seducing Cecile
Kathryn proves how ruthless she can be when she makes it her mission to deflower and destroy the reputation of Cecile Caldwell, the object of her ex’s affection. Cecile mistakenly puts her trust into Kathryn and Sebastian and finds herself in a cringe-worthy predicament. Sebastian’s actions are predatory but just shy of abusive. Cecile finds herself having to choose between facing the wrath of her overbearing mother or surrendering her body to Sebastian.
Cecile is frustratingly clueless. Sebastian never fully takes away Cecile’s power. She can stay or go but either way, there are consequences. Sebastian’s actions don’t constitute rape but calling it a seduction is giving him too much credit. Cecile is a victim of her own naivete, and this encounter, carefully orchestrated by Sebastian and Kathryn begins to strip that part of her away.
Kathryn’s Sisterly Affection
Once Sebastian agrees to help Kathryn with Cecile, their sexual flirtation accelerates. As Kathryn grinds against her stepbrother on a chaise lounge, he massages her shoulders stating “Oh, sis, you’re so tense.” It’s a jarring reminder of how twisted and dysfunctional their relationship is. At the same time, the scene is intensifying their foreplay, and it’s disconcerting how easily it is to become aroused by this taboo relationship. Kathryn brings Sebastian just to the verge of climax, exerting her power while reminding him of what’s at stake.
Sebastian Blackmails Greg
Cruel Intentions does fail to treat homosexuality with any sensitivity or political correctness. Several characters use pejorative terms that are grating to hear today. The belief that being a homosexual is deviant or shameful is central to Sebastian’s plan to manipulate Annette. Sebastian blackmails the school’s football star and longtime friend of Annette, Greg (Eric Mabius), by threatening to tell his father his pride and joy is a “fudgepacker.”
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This whole storyline could have been handled with more finesse even though Sebastian doesn’t hold Greg in any more contempt just because he’s gay. This storyline feels like it was put in for shock value, and at the time, it succeeded. Twenty years later, it’s more surprising this would give Sebastian any leverage.
Sebastian Breaks It Off With Annette
Kathryn is all about power, particularly using her sexuality to both attain and keep it. As Sebastian begins to slip through her grasp, she’s threatened and jealous, but instead of Sebastian seeing her insecurities, she exploits his. Watching him break things off with Annette, knowing she compromised everything she believes in to be with him is brutal. It’s the only time in the entire film Sebastian is vulnerable and sympathetic and at the same time loathsome and weak.
Annette undergoes a range of emotions from love to confusion to hatred, and as the tears stream down Sebastian’s face, There’s a moment when it feels like he’ll finally make the right choice, but it slips away. The fact that Witherspoon and Phillippe were a couple offscreen at the time makes the scene that much more raw.
Kathryn’s Double Cross
After Sebastian does everything Kathryn asks him to do, he comes to collect what she owes, Kathryn reveals her real agenda. It didn’t start out that way, but after watching Sebastian fall in love with Annette and knowing she lost him, she destroys him. Kathryn is no longer playing a game, or it’s not the one they both started.
Kathryn humiliates and emasculates Sebastian, breaking him down just as she does everyone else who gets in her way. Kathryn turns out to be far more dangerous than Sebastian. Of these two former allies turned adversaries, at least Sebastian learns he’s capable of love. Watching them spar as equals is enjoyable but seeing her eviscerate him is unexpected.
Exposing Kathryn
Kathryn goes to great lengths to protect her pristine reputation because it’s her disguise. She hides behind it, fooling adults and peers alike, as she orchestrates these Machiavellian schemes. Her reputation is currency, and she’s able to trade it as long as it means something.
Once Sebastian’s journal becomes public, she sees her status, and the image she has so carefully crafted being stripped away. One moment she’s feigning remorse over Sebastian, and the next, her victims are exacting their revenge. She’s grown impervious to the depravity of her actions. Even though Kathryn sheds some tears, it’s not for her sins, but because she gets caught.
Sebastian Sacrifices Himself For Annette
Sebastian finally finds a way to redeem himself which is why it’s inevitable that his love story with Annette can’t have a happy ending. His modern-day equivalent of a duel with Ronald (Sean Patrick Thomas) spirals out of control. Sebastian and Kathryn’s actions have consequences as their pawns begin to react in ways the master manipulators can’t foresee. But Sebastian isn’t supposed to die. He does so to save Annette, completing the villain’s transformation into not such a bad guy, and even surprisingly a bit of a martyr thanks the posthumous release of his journal at his memorial service.
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