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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)
1,120 ( 195)
7 wins & 13 nominations. See more awards »



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


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, 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 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

Plot Keywords:

virgin | seduction | bet | wager | revenge | See All (131) »


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:





| |

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)


$38,201,895 (USA) (30 July 1999)

Company Credits

Show detailed on  »

Technical Specs


Sound Mix:



Aspect Ratio:

1.85 : 1
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Did You Know?


Roger Kumble began writing the script the day his 1997 play d girl, starring David Schwimmer. See more »


When Sebastian goes to see Annette you can see her bra above her top but in the next shot you can't see it anymore. See more »


[reading a virgin's manifesto]
Kathryn: "Why I Plan to Wait" by Annette Hargrove, Kansas City, Kansas. Jesus Christ, is she for real?
Sebastian: Oh, she's daddy's little angel, a paradigm of chastity and virtue.
See more »


Referenced in Gossip Girl: Chuck in Real Life (2008) See more »


Trip on Love
Written by Tom Kimmel and Liz Vidal
Performed by Abra Moore
Courtesy of Arista Records Inc.
Published by WB Music Corp./Maverick Music & Samaxian Music
See more »

Frequently Asked Questions

See more (Spoiler Alert!) »

User Reviews

C(R)OOL Intentions
3 March 2001 | by (Palmerston North, New Zealand) – See all my reviews

This film (based on the 1988 hit 'Dangerous Liasons' starring Glenn Close, Michelle Pfieffer and John Malkovich) is a great movie intended for the older teenagers, and stars fine young acting talent.

Rich kid Kathryn ('Buffy The Vampire Slayer's Sarah Michelle Gellar) bets her equally jaded step-brother Sebastian (Ryan Phillippe; 'I Know What You Did Last Summer', which co-starred Sarah) that he can't seduce good girl, and virgin, Annette (played by Ryan's real-life wife Reese Witherspoon).

Along the way, Kathryn tries to help sexually-inexperienced Cecile (Selma Blair) get some action in her life, while she starts screwing Cecile's ex-music instructor! Sound weird? It is. It's basically about 2 rich snobs who mess with the lives of those around them, just because their lives get boring.

This film also stars Joshua Jackson ('The Skulls', 'Urban Legend', TV's 'Dawson's Creek) as Sebastian's gay best friend, who also gets involved in the use or be used storyline. Fellow teen-movie star Tara Reid ('Urban Legend', 'American Pie') also has a small role, as Sebastian's psychiatrists's daughter.

This film is pretty intense and deals with sex, drugs, seduction and alienation in a brave, way that makes it appealing to all teenagers. Not for the light hearted, more daring than anything like 'She's All That' and 'Never Been Kissed', but it's still good fun!

79 of 114 people found this review helpful.  Was this review helpful to you?

Message Boards

Recent Posts
TV show poster vincent-charlebois
Sebastian should have ended up with Katherine. FridaJosefin
What if Anette was the one who had cruel intentions! aplapple
How does Annette inherit Sebastian s car at the end of movie raydesant56
They're high school students? saikano_75
Are Sebastian and Kathryn Sociopaths? roboto85
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