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Cruel Intentions (1999)

R  |   |  Drama, Romance  |  5 March 1999 (USA)
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Ratings: 6.9/10 from 142,539 users   Metascore: 56/100
Reviews: 747 user | 100 critic | 24 from Metacritic.com

Two wealthy step-siblings of an elite Manhattan prep school make a wager: to de-flower the new headmaster's daughter before the start of term.



(novel), (screenplay)
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7 wins & 13 nominations. See more awards »



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Cast overview, first billed only:
Herta Ware ...
Mrs. Sugarman
Hiep Thi Le ...


Kathry Mertieul 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, the headmaster of their school's daughter, 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 Cecil, 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 ruins Cecil's reputation as revenge on Kat's ex-boyfriend, who left her for Cecil.

Plot Summary | Plot Synopsis

Plot Keywords:

virgin | love | seduction | bet | wager | See All (133) »


Are you in, or are you out? 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:





| |

Release Date:

5 March 1999 (USA)  »

Also Known As:

Cruel Inventions  »

Box Office


$10,500,000 (estimated)

Opening Weekend:

$13,020,565 (USA) (5 March 1999)


£4,080,631 (UK) (13 August 1999)

Company Credits

Show detailed on  »

Technical Specs


Sound Mix:



Aspect Ratio:

1.85 : 1
See  »

Did You Know?


The Valmount townhouse interiors were built and shot on sound stages in Los Angeles while the exterior scenes were filmed in New York City. See more »


Cameraman and crane visible in the front windshield of Sebastian's car while driving with Annette. See more »


Mrs. Sugarman: Oh, did I ever tell you the time, when my late husband sent me...
Sebastian: Yes, you already did, Mrs. Sugarman.
Mrs. Sugarman: Oh, I did?
Sebastian: Right after we played backgammon, Mrs. Sugarman.
Mrs. Sugarman: Oh! We played backgammon?
Sebastian: Uh huh. You beat me three times.
Mrs. Sugarman: I did?
Sebastian: Yup. Then I fucked your daughter.
Mrs. Sugarman: Excuse me?
Sebastian: I said, would you care for some water?
See more »


Referenced in Sex at 24 Frames Per Second (2003) See more »


You Could Make a Killing
Written and Performed by Aimee Mann
Courtesy of DGC Records
Under license from Universal Music Special Markets
Published by Aimee Mann
See more »

Frequently Asked Questions

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User Reviews

Clever, witty and very sensual
2 May 2010 | by (Portugal) – See all my reviews

In this film wealthy prep school student Kathryn (Sarah Michelle Gellar) bets her stepbrother Sebastian (Ryan Phillipe) that he can't deflower the virginal Annette (Reese Witherspoon) before the school year begins. If he fails to accomplish this task, Kathryn gets his Jaguar Roadster; if he succeeds, he gets an evening of pleasure with Kathryn.

I just finished watching Cruel Intentions and what a pleasant surprise this film turned out to be. I guess the best way to describe it is as a sexy and seductive thriller. The film is very clever and bold but above all, extremely engaging and entertaining. Dealing with this kind of subject...making this kind of film...it's definitely not easy. Usually these kind of films come off somewhat "fake" and lame; corny, whatever you want to call it. Thankfully, Cruel Intentions went the other way, probably thanks to the witty and sharp dialogue and a very good direction.

Ryan Phillippe delivered a terrific performance and so did Reese Witherspoon. I was actually a bit disappointed with Sarah Michelle Gellar, her acting was not very convincing at times to say the least but honestly, the story is so engaging that I was able to overlook that flaw. Another aspect that really took me by surprise was the musical score. Cruel Intentions has one of the best soundtracks I have ever seen in films. There's some great well known songs like Skunk Anansie's "secretly" and Placebo's "every me and every you", but there's also some fast paced instrumental tracks throughout the film that really compliment the scenes. Overall, a great watch and so much more then a teen film.


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