Cruel Intentions (1999) – Seduction, Power, and Deceit in High Society
Genre: Drama / Romance / Thriller
Director: Roger Kumble
Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Cruel Intentions is a slick, provocative reimagining of the 18th-century French novel Les Liaisons Dangereuses, transplanted into the scandalous world of wealthy Manhattan prep school teens. Directed by Roger Kumble, this 1999 teen drama walks a sharp line between soap opera and psychological chess game, offering a twisted tale of manipulation, seduction, and betrayal.
Sebastian Valmont (Ryan Phillippe) is a charming but cold-hearted playboy who, along with his equally cunning stepsister Kathryn Merteuil (Sarah Michelle Gellar), amuses himself by manipulating others for sport. Kathryn challenges Sebastian to deflower Annette Hargrove (Reese Witherspoon), the virtuous daughter of their school’s new headmaster, who has publicly vowed to wait for true love. But as Sebastian grows closer to Annette, the game turns into something far more real and destructive than either sibling anticipated.
Ryan Phillippe brings a brooding charisma to Sebastian, balancing arrogance with surprising vulnerability. Sarah Michelle Gellar is electric as Kathryn, giving one of her boldest and most daring performances. Reese Witherspoon provides a strong emotional anchor as the genuinely pure-hearted Annette, and Selma Blair’s comedic innocence as Cecile brings levity to the darker undertones.
With its razor-sharp dialogue, opulent settings, and sexually charged power dynamics, Cruel Intentions pulses with late-’90s attitude and style. The film’s moody soundtrack—featuring The Verve’s “Bitter Sweet Symphony” in its iconic final scene—has become inseparable from its legacy.
Though some critics at the time dismissed it as trashy or overly stylized, the film has since earned cult status for its audacity, glossy execution, and biting portrayal of emotional manipulation among the elite. It’s melodramatic, yes, but unapologetically so—and smarter than it first appears.
Cruel Intentions is a seductive descent into moral decay dressed in school uniforms, a twisted love story that lingers in the mind with equal parts scandal and sincerity.
