Cruel Intentions, released in theaters on March 5, 1999, remains a deliciously dark and undeniably entertaining teen drama that has earned its place as a cult classic. It’s a film that revels in its own scandalous nature, delivering a heady mix of seduction, manipulation, and sharp-tongued dialogue that continues to captivate audiences.
Sarah Michelle Gellar delivers a tour-de-force performance as Kathryn Merteuil, the manipulative and cunning queen bee of an elite Manhattan prep school. Gellar’s portrayal of Kathryn’s icy charm and ruthless ambition is both mesmerizing and terrifying. She perfectly captures the character’s wicked wit and her insatiable desire for control.
Ryan Phillippe shines as Sebastian Valmont, Kathryn’s equally manipulative stepbrother and partner in crime. Phillippe’s performance is both seductive and vulnerable, portraying Sebastian’s struggle between his desire for conquest and his growing feelings for Annette. Their on-screen chemistry is electric, fueling the film’s central conflict with palpable tension.
Reese Witherspoon delivers a charming and nuanced performance as Annette Hargrove, the virtuous and naive student who becomes the target of Kathryn and Sebastian’s twisted game. Witherspoon effectively portrays Annette’s innocence and her eventual awakening to the darker side of human nature.
Selma Blair is perfectly cast as Cecile Caldwell, the vulnerable and easily manipulated student who becomes a pawn in Kathryn’s schemes. Swoozie Kurtz, Louise Fletcher, Joshua Jackson, and Tara Reid add memorable supporting performances, enriching the film’s ensemble.
Roger Kumble’s direction is stylish and assured, creating a visually appealing and atmospheric film. The soundtrack, featuring iconic 90s alternative rock hits, perfectly complements the film’s mood and tone.
The film’s pacing is brisk, keeping the audience engaged with its twists and turns.
Cruel Intentions is more than just a teen drama; it’s a modern adaptation of the classic 1782 novel Les Liaisons Dangereuses, exploring themes of power, seduction, and the corrupting influence of wealth and privilege. The film’s dialogue is sharp and witty, filled with quotable lines and memorable exchanges.
The film’s appeal lies in its willingness to embrace its own darkness and its unapologetic portrayal of its characters’ flaws. It’s a film that revels in its scandalous nature, creating a world of intrigue and manipulation that is both thrilling and unsettling.

Ryan Phillippe and Sarah Michelle Gellar in Cruel Intentions (Photo/Columbia Pictures)
Reception for Cruel Intentions
Cruel Intentions grossed $13 million on its opening weekend, finishing second at the box office behind Analyze This ($18.4 million) starring Robert De Niro and Billy Crystal.
The film would gross $75.9 million in its theatrical run.
Roger Ebert gave the film three out of four stars in his review, saying it was “smart and merciless in the tradition of the original story”
Lasting Legacy
Cruel Intentions remains a guilty pleasure for many. It’s a film that has earned its place as a cult classic, celebrated for its iconic performances, its sharp dialogue, and its deliciously wicked plot. It’s a reminder that sometimes, the most dangerous games are the ones we play with our hearts.
