Cruel Intentions

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2:19

Cruel Intentions

R

1999

1h 37m

Drama

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Tomatometer

Popcornmeter

55%

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120 Reviews

80%

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250,000+ Ratings

Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian's (Ryan Phillippe) and Kathryn's (Sarah Michelle Gellar) deliciously diabolical wager of sexual conquest when she writes an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. However, Sebastian gets more than he bargained for as he attempts to woo Annette into his bed.

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Critics Consensus

This darkly comic drama and its attractive young cast are easy on the eyes, but uneven performances and an uninspired script conspire to foil Cruel Intentions.

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Kristy Puchko

Pajiba

Mar 27, 2019

20 years later, you can see the charm that made Witherspoon a star, appreciate Blair's comedic splendor, and recognize that Phillippe was handsome and is also in this movie.

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Kevin Thomas

Los Angeles Times

Mar 21, 2019

Cruel Intentions is a stretch for all concerned, including the targeted audience, one that pays off handsomely--and works for older moviegoers as well.

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Andrew Sarris

Observer

Mar 21, 2019

At this infantile level of appraisal, I suspect that Ms. Gellar and Mr. Phillippe may have a harder time next summer than last.

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John Stark

Mac the Movie Guy

May 23, 2026

84/100

I have nostalgia problems. cruel Intentions leaned harder into manipulation, sex, and cruelty. A very delicious guilty pleasure 25 years later, Roger Kumble’s sexy thriller can still put it wherever it wants.

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Sharai Bohannon

A Nightmare On Fierce Street Podcast

Mar 8, 2026

4/5

'Cruel Intentions' isn't perfect, but she's still fun and formative for teen audiences in a way that films today are not. We need more of this for today's youth.

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Simon Gallagher

Screen Rant

Nov 19, 2024

8/10

A steamy, provocative teen drama with improbably high stakes that you really shouldn't watch with your parents. Or your kids. Or your step brother.

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Thyaagu C

@Thyaagu Aug 25, 2026

3.75 ⭐️ She walked in, chose chaos, and absolutely owned it. Sarah Michelle Gellar was phenomenal as Kathryn, with Ryan and Reese bringing enough highs and lows to make this twisted little game work. A messy, dark, & addictive ride!!

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Horror fan 4

@Horrorfan4life Aug 25, 2026

One of the greatest movies of the 1990's. This movie is stacked with stars. I love this story of a guy trying lay the deans daughter. All the while step siblings are wanting to get it on. Eventually this turns into a revenge movie and Reese Witherspoon is brilliant in setting that up. These step siblings are ruthless but in the end they deserve what they get. Tim Treakle

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Chris S

@Janomi Jul 20, 2026

Cruel Intentions is good because it has such a sharp, seductive late-’90s identity. The expensive clothes, Manhattan privilege, sexual games, secrets, betrayals, and glossy cruelty give the movie a style that is just as important as the story. The soundtrack is also one of its biggest strengths and remains one of the most memorable of the decade. Sarah Michelle Gellar is the best thing about the film. Kathryn is polished, manipulative, cruel, and completely poisonous, and Gellar plays her with icy confidence. Ryan Phillippe and Reese Witherspoon give the movie its emotional spine, with Sebastian’s arrogance slowly giving way to vulnerability and Annette bringing sincerity and moral clarity. The teen update of Dangerous Liaisons is clever, and the cruelty translates surprisingly well into this world. The heightened tone can become ridiculous, but that is also part of the appeal. It is stylish, mean, overdramatic, and very watchable.

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mbryanf T.

@mbryanf Jul 2, 2026

I first saw this movie back in ’99, and I watched it again in ’26. Honestly, it was so ahead of its time, and it’s become a must-watch classic from the ‘90s. The four main actors were practically unknowns then, and Cruel Intentions was definitely a big break for Witherspoon, Gellar, and Blair.

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Elza R.

@elzas_movies May 22, 2026

A little unconvincing and rushed, but the ending is what makes it a great movie and one of my favorites.

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salvationDANCE T

@DanceHH81 Apr 3, 2026

cult classic! a must know in pop-culture!!

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Roger Kumble

Director

Sarah Michelle Gellar

Kathryn Merteuil

Ryan Phillippe

Sebastian Valmont

Reese Witherspoon

Annette Hargrove

Selma Blair

Cecile Caldwell

Louise Fletcher

Helen Rosemond

Cruel intentions: Official Clip - The Black Man is Gone

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Cruel Intentions: Official Clip - Practice Makes Perfect

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Cruel Intentions: Official Clip - Funny Faces

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Cruel Intentions: Official Clip - The Bet

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Cruel Intentions: Official Clip - Sebastians' Journal

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Synopsis

Annette (Reese Witherspoon) unwittingly becomes a pawn in Sebastian's (Ryan Phillippe) and Kathryn's (Sarah Michelle Gellar) deliciously diabolical wager of sexual conquest when she writes an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. However, Sebastian gets more than he bargained for as he attempts to woo Annette into his bed.

Director: Roger Kumble
Producer: Neal H. Moritz
Screenwriter: Roger Kumble
Distributor: Columbia Pictures, Sony Pictures Entertainment
Production Co: Columbia Pictures, Newmarket Capital Group
Rating: R (Language|Drug Use|Sexual Situations|Strong Sexual Dialogue)
Genre: Drama
Original Language: English
Release Date (Theaters): Mar 5, 1999, Wide
Rerelease Date (Theaters): Mar 22, 2019
Release Date (Streaming): Mar 28, 2014
Box Office (Gross USA): $38.6M
Runtime: 1h 37m
Sound Mix: Dolby Stereo, Dolby A, SDDS, Surround, Dolby Digital, Dolby SR
Aspect Ratio: Flat (1.85:1)

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