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Cruel Intentions (1999)

R | | Drama, Romance | 5 March 1999 (USA)
0:31 | Trailer

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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.



(novel), (screenplay)
458 ( 49)
7 wins & 14 nominations. See more awards »



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Cast overview, first billed only:
Mrs. Michalak
Herta Ware ...


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, no one 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:





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Release Date:

5 March 1999 (USA)  »

Also Known As:

Cruel Inventions  »


Box Office


$10,500,000 (estimated)

Opening Weekend USA:

$13,020,565, 7 March 1999, Wide Release

Gross USA:


Cumulative Worldwide Gross:

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Company Credits

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Technical Specs


Sound Mix:



Aspect Ratio:

1.85 : 1
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Did You Know?


Fred Norris, head writer and cast member of The Howard Stern Show (1987), has a small part, credited as the Meter Maid - Ryan Phillippe is a huge Howard Stern fan. See more »


Sebastian tells Kathryn about what has happened "between Annette and I." The correct grammar is "between Annette and me." See more »


Gretchen (a hooker): Books are for fags.
Sebastian: Books are for fags? Then weep for the future.
See more »


Spoofed in Not Another Teen Movie (2001) See more »


Written by Pauline Taylor, Maxi Jaxx, Roland 'Rollo' Armstrong (as Rollo Armstrong) and Sister Bliss (as Ayalah Bentovim)
Performed by Faithless
Courtesy of Cheeky Records/Arista Records Inc.
Published by Champion Music, BMG Music Publishing Ltd/BMG Songs Inc. & WB Music Corp./Warner Chappell Music Ltd.
Contains a large sample of Pauline Taylor's "Addicted"
Written and Performed by Pauline Taylor
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Frequently Asked Questions

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User Reviews

Cruel Intentions — High society teens ruining the reputation of others with sex and deceit
20 December 2012 | by See all my reviews

Cruel Intentions is the perfect romantic drama. This fruit did not fall far from the Romeo & Juliet tree. Romance, love, plots, and drama are all turned modern and splendidly rendered. Add to that a great soundtrack, beautiful shots, tension, hot eroticism, sex, and you get the perfect mix for that type of flick.

All the actors are playing their best game, without exception. The story line is gripping, interesting, and it delivers without fail. The twists are numerous, non-repetitive, and scandalous.

This movie showed everybody that Sarah Michelle Gallar could play anything, because this role is as far from the vampire slayer as you can get.

A must see.

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