Cruel Intentions wants to be a sharp, dangerous teen drama. It mostly gets the surface right — the clothes, the New York setting, the glossy tone — but underneath, it plays safe. The film, directed by Roger Kumble and adapted from Pierre Choderlos de Laclos’ 1782 novel Les Liaisons dangereuses, trades the original’s moral weight for a pop-culture gloss. It succeeds at style and falls short on stakes.
Trailer, via Sony Pictures Entertainment.
Kathryn and Sebastian: A Bet With Rules
The setup is simple. Sebastian Valmont, played by Ryan Phillippe, is a master of manipulation. He seduces women as a sport, and the film opens with him looking for a new target. That target is Annette Hargrove, the daughter of his new school headmaster. She is staunchly opposed to sex before love, which makes her the perfect challenge.
Sebastian’s stepsister, Kathryn Merteuil, played by Sarah Michelle Gellar, agrees to a wager with him. If Sebastian fails to seduce Annette, Kathryn gets his vintage Jaguar XK140. If he wins, Kathryn will finally have sex with him. The terms are clear, the stakes are personal, and the film spends its runtime trying to keep the audience invested.
Annette and Cecile: Two Innocents, One Scheme
The film introduces Annette Hargrove, played by Reese Witherspoon, as the girl Sebastian targets. She is the moral center of the story, and the film leans on her resistance to create tension. Her friend Greg, played by Joshua Jackson, is a closeted homosexual who knows Sebastian’s reputation. Sebastian blackmails him into convincing Annette that Sebastian is a good man.
Meanwhile, Kathryn has her own scheme. She wants revenge on her ex-boyfriend, Court Reynolds, who left her because of her promiscuity. She begins to manipulate Cecile Caldwell, played by Selma Blair, a naive and innocent girl. Cecile’s mother warns Annette about Sebastian, and Sebastian agrees to corrupt Cecile as revenge.
The Bet Runs Its Course
As the film progresses, Sebastian’s attempts to seduce Annette fail. He suspects Greg of being responsible and forces him to change Annette’s mind. Later, Sebastian learns that Cecile’s mother warned Annette, so he corrupts Cecile instead. 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 then convince Ronald to fight for Cecile by writing her a love letter. Sebastian uses that letter 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.
The Feelings That Break the Bet
Spending time with Annette, Sebastian develops genuine feelings for her. He is attracted to her honesty and her ability to make the normally stoic Sebastian laugh. He kisses her, but she resists because she reciprocates his feelings and fears she cannot restrain herself around him.
This is the heart of the film’s problem. The bet is a clever premise, but the film does not trust its own rules. Sebastian’s feelings are real, but the film keeps pulling back from letting them matter. The result is a story that promises danger and delivers a romance that never quite commits to either side.
The Supporting Cast
The film is packed with talent beyond its leads. Louise Fletcher plays Helen Rosemond, based on Madame de Rosemonde. Christine Baranski plays Bunny Caldwell, based on Madame de Volanges. Swoosie Kurtz plays Dr. Regina Greenbaum, and Tara Reid plays Marci Greenbaum. Fred Norris plays a meter maid.
These actors fill out the world of wealthy teenagers in New York City, but the script does not give them much to do. They exist to support the central triangle of Kathryn, Sebastian, and Annette, and the film rarely lets them breathe.
What Works
The film’s performances carry it when the writing falters. Phillippe and Gellar are magnetic together, and the chemistry between them is the best reason to watch. Witherspoon grounds the story as Annette, giving the film a center of gravity it otherwise lacks.
The direction is competent, and the film looks expensive. It captures the glossy, privileged world of wealthy teens in New York City with confidence. The tagline, “In the game of seduction, there is only one rule: Never fall in love,” is repeated often enough to become a running joke.
What Falls Short
The film’s biggest failure is its unwillingness to commit to its own rules. The bet between Kathryn and Sebastian is the engine of the story, but the film keeps finding ways to let Sebastian win. When Sebastian’s feelings for Annette start to emerge, the film retreats to the safety of a conventional romance.
The pacing also suffers. At 97 minutes, the film should move fast, but it drags in stretches. The middle section, where Sebastian corrupts Cecile, feels like filler. The film is too eager to get to the resolution, and it rushes through the climax.
A Cult Classic With Limits
Despite its flaws, Cruel Intentions became a cult classic. It spawned a prequel in 2000, a standalone sequel in 2004, a jukebox musical in 2015, and a 2024 television series. That success is not surprising. The film is stylish, the performances are strong, and the premise is irresistible.
But as a film, it is limited. It is a polished, entertaining adaptation that never fully earns its ambition. The original novel is about the corrupting power of pleasure, and the 1988 film version explored that theme with genuine dread. This version is more interested in the thrill of the chase than the cost of winning.
“In the game of seduction, there is only one rule: Never fall in love.”
That line sums up the film’s attitude. It is a clever slogan, but it is not a philosophy. The film treats the game as a sport, not a tragedy. And while that approach works for a while, it eventually leaves the audience wanting something deeper.
Cruel Intentions is a solid, enjoyable teen drama with a great cast and a sharp surface. It is not a great film, but it is a well-made one. The difference is small, but it matters.
Key Facts Box
- Runtime: 97 minutes
- Director: Roger Kumble
- Written by Roger Kumble
- Starring: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
- Released: March 5, 1999
- Gross: $75.9 million worldwide
The film is a worthy entry in the genre, but it never quite reaches the heights of its ambitions. It is a fun watch, a guilty pleasure, and a reminder that style is not the same as substance.
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