In the gilded halls of an elite New York City prep school, manipulative stepsiblings make a dangerous wager: if a charismatic playboy can seduce the chaste daughter of their new headmaster, he wins glory and pleasure — but the game quickly spins into a collision of desire, betrayal, and ruined reputations.
Cruel Intentions is a 1999 American teen romantic drama written and directed by Roger Kumble, adapted from the 1782 French novel Les Liaisons dangereuses by Pierre Choderlos de Laclos, but transposed to modern-day New York City. The film stars Sarah Michelle Gellar as the cunning Kathryn Merteuil, Ryan Phillippe as her charming but ruthless stepbrother Sebastian Valmont, Reese Witherspoon as Annette Hargrove — the virtuous girl caught in their scheme, and Selma Blair as the naive Cecile Caldwell. Set among affluent teenagers navigating wealth, sex, and manipulation, the story unfolds as Sebastian accepts Kathryn’s bet to seduce Annette, who plans to remain chaste until marriage. Their tangled plots of vengeance, desire, and cruelty spiral into emotional and moral consequences no one fully expects. Produced by Columbia Pictures and Original Film, the movie was released widely in the United States on March 5, 1999, and became a significant box office success, grossing about $75.9 million worldwide against a modest budget. Though it received mixed critical reviews, its bold portrayal of teenage ambition and betrayal has helped it endure as a cult classic and a defining teen drama of the late ’90s.