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Cruel Intentions (1999)

R | | Drama, Romance | 5 March 1999 (USA)
2:20 | Trailer
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.


Roger Kumble


Choderlos de Laclos (novel), Roger Kumble (screenplay)
897 ( 14)
8 wins & 14 nominations. See more awards »





Cast overview, first billed only:
Sarah Michelle Gellar ... Kathryn Merteuil
Ryan Phillippe ... Sebastian Valmont
Reese Witherspoon ... Annette Hargrove
Selma Blair ... Cecile Caldwell
Louise Fletcher ... Helen Rosemond
Joshua Jackson ... Blaine Tuttle
Eric Mabius ... Greg McConnell
Sean Patrick Thomas ... Ronald Clifford
Swoosie Kurtz ... Dr. Greenbaum
Christine Baranski ... Bunny Caldwell
Alaina Reed-Hall ... Nurse (as Alaina Reed Hall)
Deborah Offner ... Mrs. Michalak
Tara Reid ... Marci Greenbaum
Herta Ware Herta Ware ... Mrs. Sugarman
Hiep Thi Le ... Mai-Lee


Kathryn Merteuil and Sebastian Valmont are seductive, manipulative step-siblings who get what they want when they want it. Kathryn makes a bet with Sebastian: Sebastian must bed Annette, daughter of the headmaster at their school, before the end of summer break. Annette has stated that she would wait until love and marriage to sleep with a man. If Kathryn wins, she gets Sebastian's vintage 1959 Jaguar Roadster. If Sebastian wins, he gets Kathryn, the only girl he knows he'll never have. Also in play is Cecile, a naïve girl whose mother had enlisted Kathryn to help her fit in at her new school. However, Kathryn (with Sebastian's help) plans to ruin Cecile's reputation as revenge on Kat's ex-boyfriend, who left her for Cecile.

Plot Summary | Plot Synopsis


Everyone does it...but nobody talks about it. See more »


Drama | Romance

Motion Picture Rating (MPAA)

Rated R for strong sexual dialogue and sexual situations involving teens, language and drug use | See all certifications »

Parents Guide:

View content advisory »

Did You Know?


Porn star Alisha Klass appeared as a cheerleader, but her brief scene was cut. You can see a glimpse of her in the lower right hand part of the screen when Sebastian (Ryan Phillippe) is talking to Annette (Reese Witherspoon) on the phone. See more »


In the luncheon scene in Aunt Helen's yard, she leans down to hug Sebastian after saying the line, "You two are the best!" In one shot, she moves her left hand to his left shoulder, but in the next shot (close-up) her hand is not on his shoulder. See more »


Greg McConnell: So I pull out my dick, and I shove it right in her face. And I'm like, the hell is this? Grandma with a birthday present? Suck it ya dumb bitch!
See more »

Alternate Versions

There was a line of dialogue cut from the US version which appears in the UK cut. After Kathryn views the videotape of Cecil and Ronald she comments: 'F*ck her already' See more »


Referenced in 100 Greatest Sexy Moments (2003) See more »


Written by Skin and Len Arran
Performed by Skunk Anansie
Courtesy of Virgin Records Limited
Published by Chrysalis Music
See more »

User Reviews

strong beginning, weak ending
3 August 1999 | by Buddy-51See all my reviews

For exactly two-thirds of its 97 minute running time, "Cruel Intentions" scores as a nasty-minded, wryly satiric and even mildly courageous teen update of "Dangerous Liaisons." But, like so many movies with one eye cocked towards the boxoffice, "Cruel Intentions" loses its nerve and settles ultimately for comfortable, safe and hopelessly dull conventionality. Ryan Phillippe and Sarah Michelle Gellar portray a wicked pair of step siblings who operate together to prey sexually upon unsuspecting victims, manipulating others to achieve their goals of personal conquest and revenge. It's refreshing to encounter protagonists who make no excuses for their amorality and instead allow themselves to be completely guided by their own self-serving impulses, totally unmindful of the consequences to others. Their schemes are acted out with a callous gleefulness and self-absorbed relish that raises the film to a level of surprisingly sophisticated satire and audacity. But, when Sebastian encounters his ultimate challenge - a midwestern virgin played by Reese Witherspoon, who has publicly declared in a magazine her decision to wait for true love before offering herself to a man - he falls under her charms and suddenly transforms from coldhearted predator to mushheaded romantic. This is the major problem with the film. Sebastian is valid and interesting as a character as long as he stays within the realm of sly manipulator and acerbic scoundrel. When he is called upon to function as a dashing romantic figure, he loses both credibility and uniqueness - and the film itself goes into a freefall tailspin. For, as Sebastian undergoes his sudden conversion, all the sharply satiric wit simply drains out of the film. We're ultimately left with little more than unconvincing melodrama, inappropriately tragic overtures and a silly evildoers-do-not-prosper resolution. What a pity to see yet another in a long line of movies that start out with bright promise, but which finally end up renaging on their initial courageousness, leaving the audience in perpetual frustration.

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Frequently Asked Questions

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English | Vietnamese | French

Release Date:

5 March 1999 (USA) See more »

Also Known As:

Cruel Inventions See more »


Box Office


$10,500,000 (estimated)

Opening Weekend USA:

$13,020,565, 7 March 1999

Gross USA:


Cumulative Worldwide Gross:

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Company Credits

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Technical Specs


Sound Mix:

Dolby Digital | SDDS | DTS (Digital DTS Sound)



Aspect Ratio:

1.85 : 1
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