Cruel Intentions

In the seductive world of Manhattan's Upper East Side, morality often takes a backseat to the allure of luxury and desire. This is the setting for Roger Kumble's 1999 film, Cruel Intentions, a twisted tale of toxic relationships, deception, and manipulation, all masquerading as innocent games. The movie centers around Kathryn Merteuil, a manipulative and cunning 18-year-old played by Sarah Michelle Gellar. Kathryn's reputation as a seductress precedes her, and she's determined to prove to herself and the world that she's the queen of New York's party scene. Her stepbrother Sebastian Valmont, played by Ryan Phillippe, is equally accomplished in the art of seduction, having already lost his virginity at the young age of 10. One day, while at a luxurious dinner party, Kathryn challenges Sebastian to a game: deflower the innocent and naive Cecile Cabot, the headmaster of their prep school's daughter. Cecile is a wide-eyed and artless young woman, played by Selma Blair, who's as much a product of the wrong environment as Kathryn and Sebastian are of the right one. According to the rules of the game, if Sebastian succeeds, Kathryn promises to allow him to indulge in her own favors. However, if Sebastian loses, Kathryn gets to claim Sebastian's prized possession: his first edition of Henry Miller's "Tropic of Cancer." As the game begins to unfold, Sebastian introduces Cecile to a world of debauchery, encouraging her to abandon her virginity and seek out experience. Cecile, torn between her devotion to Sebastian and her unrequited love for him, becomes increasingly entwined in a web of deceit and misdirection. Meanwhile, Kathryn resorts to a system of deception, secretly orchestrating events to ensure Sebastian's failure. However, Sebastian becomes increasingly attracted to Cecile, and a peculiar sense of protectiveness and intimacy develops between the two, further muddying the waters. The relationship between the step-siblings is already volatile, with Sebastian harboring a deep resentment towards Kathryn. Their confrontations with each other, an undercurrent of anger, resentment, and competition, serve only to heighten their already combustible dynamic. As the summer wears on and Sebastian's intentions become clear, his unrequited love for Cecile and Kat's wily manipulation threaten to destroy the intricate façade they've constructed. Sebastian's growing attachment to Cecile forces him to navigate a fragile moral code, even as the merciless Kathryn forces him to balance his guilt with his desire. Over the course of the summer, Cat and Sebastian form a love-hate connection.