
Released in 1999, Cruel Intentions is a adaptation of Pierre Choderlos de Laclos's 1782 novel Les Liaisons dangereuses. Roger Kumble wrote and directed the film, making his feature directorial debut. Instead of the novel's French aristocratic society, the story unfolds among wealthy teenagers in Manhattan. Sarah Michelle Gellar plays Kathryn Merteuil, Ryan Phillippe plays her stepbrother Sebastian Valmont, and Reese Witherspoon plays Annette Hargrove. Selma Blair appears as Cecile Caldwell, a sheltered student whose introduction to this privileged social circle becomes part of Kathryn's revenge campaign. The change in setting preserves the source material's central machinery: seduction, manipulation, and betrayal.
The principal wager concerns Annette, the new headmaster's daughter, who has publicly declared that she intends to remain a virgin until marriage. Kathryn challenges Sebastian to seduce her. If he fails, Kathryn will receive his Jaguar; if he succeeds, she will sleep with him. Meanwhile, Kathryn targets Cecile because her former boyfriend has chosen Cecile over her. Sebastian initially treats both young women as pieces in these games, but his involvement with Annette develops into genuine affection. That emotional shift threatens the arrangement with Kathryn, whose polished public image conceals her cruelty, cocaine use, and determination to control other people.
The film's climax turns Sebastian's private record of his exploits into evidence against Kathryn. After Sebastian breaks with her manipulation, events lead to a confrontation with Ronald, Cecile's music teacher, played by Sean Patrick Thomas. Sebastian dies after being struck by a car while saving Annette. At his memorial, copies of his journal circulate, exposing Kathryn's behavior. Her cocaine is hidden inside the crucifix she wears, an object that makes her performance of religious respectability particularly pointed. The closing sequence shows Annette driving Sebastian's Jaguar while The Verve's “Bitter Sweet Symphony” accompanies the collapse of Kathryn's carefully maintained social authority.
Music is integral to several of the film's most recognizable sequences. Placebo's “Every You Every Me” accompanies the opening credits, while Counting Crows' “Colorblind” underscores Sebastian and Annette's developing intimacy. The soundtrack also includes Blur's “Coffee & TV.” The film arrived during Gellar's run as the title character in Buffy the Vampire Slayer, giving her a sharply different role as a calculating antagonist. Its afterlife includes Cruel Intentions 2, released in 2000, a prequel assembled from material originally produced for the unbroadcast television project Manchester Prep. Amy Adams plays Kathryn in that film, taking over the role performed by Gellar.
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