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Cruel Intentions (1999)

R  |   |  Drama, Romance  |  5 March 1999 (USA)
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Ratings: 6.9/10 from 142,500 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) »


In the game of seduction, There is only one rule: Never fall in love 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:

$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?


When Sebastian is handing Kathryn the Seventeen magazine to read. On the cover is Jennifer Love Hewitt who previously stared with Sarah Michelle Gellar and Ryan Phillipi from I know what you did Last Summer from 2 years previously. See more »


When Dr. Greenbaum takes a note on billing for the book, a line is visible about Sebastian verging on psychopathic but it is misspelled as 'pyshopathic'. See more »


Sebastian: It's not like you have a husband - unless you're married to Jesus.
See more »


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


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

Frequently Asked Questions

See more (Spoiler Alert!) »

User Reviews

They're old enough to know better and too young to care!
21 February 2002 | by (Hamilton, Australia) – See all my reviews

I have recently been seeing a psychiatrist about a few troubles. In one of his sessions, he bought up about the movie Cruel Intentions, which I absolutely loved. He said he loved the start of the movie where the evil Sebastian says to the Psychologist `You have beautiful legs, I would love to photograph them'. This then sets the tone for one of the best teen films that the world has seen. Based on the movie Dangerous Liaisons, Cruel Intentions goes down as one of my top five favourite films of all-time.

A sex-obsessed rich boy Sebastian sets out to win his greatest "conquest" - a girl who has proclaimed in a Teen magazine that she will wait until marriage to lose her virginity. The teen is egged on by his sister, Catherine, an evil scheming girl in her own right. The two have a wager on whether Sebastian can achieve his conquest. If he wins, he gets a night of bliss with his stepsister, if she wins, she keeps his most prided possession, his Jaguar convertible!

Well this is a brilliant backstabbing, bitchy, love and hate war movie. I cannot remember a movie like it in my time. The theme of the movie was priceless. Having two rich hobnob kids toying with various people's emotions in their neighborhood was just great. In fact it is not at all silly to think that this does not happen in real life, because if you don't believe that then you are very naïve.

There are many people who need to be praised for this classic movie. Director Roger Kumble did a great job in bringing this movie to our screens. He added so many little `steamy' pieces to this movie that it was never going to fail. Then you have the producer Neal H. Moritz who also allowed this film to shine. He gave this film all the right production touches, which I can only praise.

Then you have the wonderful cast that was assembled for Cruel Intentions. The main star for this film would have to be the gorgeous Sarah Michelle Gellar. She was outstanding as the horrible Catherine. Her character while at times was extremely hard to like, she was almost too hard to not want to like. I mean she was every guy's fantasy. Sexually liberated (and not afraid to admit it), then all she wanted to do is screw up all her enemies at the same time. Then you have the patronising and ‘stud man' Sebastian, played by Hollywood hunk Ryan Philippe. His performance in this film was also first class. I thought his character was a lot more likable then Catherine's, but you could sometimes want to strangle him for the way he screws with people, just like his stepsister does, and then still seemingly gets more women dying to be with him.

Other cast members just help to make this film an extraordinary viewing experience. Reese Witherspoon is fantastic as the pure and innocent, Annette. She helps to balance the sour bitchy side of the cast, with her friendly almost sickening goody goody side. I am looking forward to seeing Witherspoon in the comedy, Legally Blonde, directed by new Australian director Robert Luketic. Selma Blair was also very good in her role as the dumb and very naïve Cecil. The kissing scene that she has with Gellar was one of the highlights of the film, with the kiss being voted the best onscreen kiss a few years ago.

Then this film has another great side to it, that of the soundtrack. It has so many great songs on it. Placebos tune `Every me, Every you' helps start this movie off, then you get songs such as Colorblind by Counting Crows and the classy, Bitter Sweet Symphony, by the Verve. This would have to be one of the world's most popular soundtracks from where I view it.

In conclusion, Cruel Intentions is a film I can say I love and that I can learn from. People in real life do use people and do hurt them. I know this because I was involved in such a scenario not so long ago. Nothing was ever happy until it was a fight and scrag. I will go as far to admit that I was confronted with a real life Catherine, a person who was such a goody goody on the outside, but the real person on the inside is a person that loves to cause trouble and will go out of her way to do it. Anyone who is like that is a real low-life in my view. Get swept up in the nasty love triangle, ‘Cruel Intentions'!

Rating: 5 Stars or 10/10

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Sebastian should have ended up with Katherine. FridaJosefin
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