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Cruel Intentions

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Cruel Intentions

Cruel Intentions is a 1999 American teen romantic drama film written and directed by Roger Kumble, and starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, and Selma Blair. The film, set in New York City among rich high schoolers, is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses.

Initially a smaller-budget independent film, it was picked up by Columbia Pictures and widely released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Phillippe, and Witherspoon were praised and the film grossed $75.9 million worldwide. Since its release, the film has become regarded as a cult classic.

Its box office success spawned a media franchise with a prequel in 2000 and a standalone sequel in 2004, as well as a jukebox musical in 2015 and a 2024 television series.

In New York City, wealthy teenager Sebastian Valmont regularly manipulates and seduces women, but seeks someone who poses a challenge to his charm. He settles on Annette Hargrove—the daughter of his new school headmaster—who is staunchly opposed to sex before falling in love. Sebastian and his equally manipulative stepsister, the intelligent and popular Kathryn Merteuil, agree to a bet: if Sebastian fails to seduce Annette, then Kathryn gets his vintage Jaguar XK140; if he wins, Kathryn will finally have sex with him. Kathryn tries to recruit Sebastian into her own scheme to take revenge on her ex-boyfriend Court Reynolds, who left her because of her promiscuity and began dating the naive and innocent Cecile Caldwell.

Sebastian's initial efforts to seduce Annette fail as she has been informed of his reputation. He suspects Annette's friend Greg, a closeted homosexual, of being responsible and blackmails him into convincing Annette of his good nature. Later, Sebastian learns that Cecile's mother warned Annette and agrees to corrupt Cecile as revenge. Kathryn notices romantic tension between Cecile and her music teacher Ronald Clifford, and reveals this to Cecile's mother, who fires Ronald. Sebastian and Kathryn convince Ronald to fight for Cecile by writing her a love letter which Sebastian uses to lure Cecile to his bedroom, where he coerces her into receiving oral sex from him. The next day, Kathryn advises Cecile to have sex with Sebastian and be promiscuous so she can learn to please Ronald.

Spending time with Annette, Sebastian develops genuine feelings for her, attracted to her honesty and ability to make the normally stoic Sebastian laugh. He kisses Annette but she resists because she reciprocates his feelings and fears she cannot restrain herself around him. Sebastian calls her a hypocrite for rejecting the opportunity for true love and she finally relents and begins undressing, but Sebastian, confused about his own feelings, declines to have sex with her. Annette leaves the following day, but Sebastian finds her, professes his feelings, and they have sex.

A jealous Kathryn tries to seduce Sebastian but is frustrated that her hold over him has been broken by his feelings for Annette, and she convinces him that he cannot change his true nature. Sebastian plans to tell Annette the truth about the bet but Kathryn warns him that he will only destroy both his and Annette's reputations. He devastates Annette by lying that he only wanted her for sex and feels nothing for her. Sebastian tells Kathryn that he has broken up with Annette, and, having won the bet, wants his reward, but she dismisses him. Kathryn reveals that he was the true target of her scheme and that she manipulated him into feeling shame over his love for Annette for her own amusement.

Sebastian tries to contact Annette to confess the truth and beg for a second chance, but she refuses to see him. He gives her his journal, in which he has detailed Kathryn's manipulative schemes, their bet, and his true feelings for Annette. Seeking revenge, Kathryn calls Ronald, claiming that Sebastian hurt her and slept with Cecile. Ronald confronts Sebastian, and the ensuing fight migrates to the middle of the street. Annette tries to intervene but is thrown into traffic and Sebastian is hit by a taxi while pushing her to safety. Sebastian and Annette confess their love for each other before he dies from his injuries.

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