Cruel Intentions

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Cruel Intentions
Cruel intentions ver1.jpg
Theatrical release poster
Directed byRoger Kumble
Produced byNeal H. Moritz
Screenplay byRoger Kumble
Based onLes Liaisons dangereuses
by Pierre Choderlos de Laclos
Music byEdward Shearmur
CinematographyTheo van de Sande
Edited byRyan Mikel
Distributed byColumbia Pictures
Release date
  • March 5, 1999 (1999-03-05)
Running time
97 minutes
CountryUnited States
  • English
  • French
Budget$10.5 million[1]
Box office$75.9 million[1]

Cruel Intentions is a 1999 American teen romantic drama film directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is an adaptation of the novel Les Liaisons dangereuses, written by Pierre Choderlos de Laclos in 1782, but set among wealthy teenagers attending high school in New York City instead of 18th-century France.[2]

The film started as a smaller budget independent film, but was picked up by Columbia Pictures and released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised. Cruel Intentions was a box office success, earning $75 million, with two direct-to-video sequels.


In an upscale New York City mansion, wealthy and popular teenager Kathryn Merteuil (Sarah Michelle Gellar) is discussing her prep school with Mrs. Caldwell (Christine Baranski) and Mrs. Caldwell's daughter, Cecile (Selma Blair). Kathryn promises Mrs. Caldwell that she will look out for the naive Cecile. Kathryn's stepbrother, Sebastian (Ryan Phillippe), enters the room, whereupon Mrs. Caldwell reacts to him coldly and leaves with Cecile. Kathryn reveals to him that her real intention is to use Cecile to take revenge on her ex-lover Court Reynolds (Charlie O'Connell), who dumped her for Cecile. Kathryn asks Sebastian to seduce Cecile; he refuses as he is planning to seduce Annette Hargrove (Reese Witherspoon), the virgin daughter of their prep school's new headmaster who is a "paradigm of chastity and virtue". After some negotiation the two agree on a wager: if Sebastian fails to bed Annette, Kathryn gets Sebastian's vintage Jaguar XK140; if he succeeds, Kathryn will have sex with him (and anal sex is implied as Kathryn seals the bet by promising him that "you can put it anywhere" as she gestures suggestively to him).[3] It is mentioned that Sebastian keeps a journal detailing his conquests.

Sebastian's first attempt to seduce Annette fails, as she had already been told of his reputation as a womanizer. He vents to his friend, Blaine Tuttle (Joshua Jackson), who suggests that the informant might be Annette's ex-boyfriend and closeted jock, Greg McConnell (Eric Mabius), revealing to Sebastian that Greg tried to make a pass at him. Sebastian uses the information to have Blaine seduce Greg, while secretly filming their meeting. Sebastian then confronts Greg with the photographs, but the latter denies warning Annette. Greg is pressured into investigating who did, and Sebastian also orders him to present him in a good light to Annette. Later, while gushing about Sebastian to Annette, Greg discovers that the culprit is Cecile's mother, Mrs. Caldwell. Wanting revenge on the Caldwells, Sebastian agrees to seduce Cecile.

Meanwhile, Cecile's music teacher, Ronald Clifford (Sean Patrick Thomas), is in love with her. Cecile confesses this to Kathryn. Kathryn tells Mrs. Caldwell about Ronald and Cecile's romance, and Mrs. Caldwell orders Cecile to end it, out of racism. Sebastian, in turn, calls Cecile to his house, ostensibly to give her a letter from Ronald. There he blackmails Cecile in order to perform oral sex on her. The next day, Cecile confides in Kathryn, who advises her to learn from Sebastian so that she can make Ronald happy in bed.

Sebastian begins to fall in love with Annette, who returns his feelings but still resists him. Sebastian calls her a hypocrite because she claims to be waiting for her one true love, but when her one true love chooses to love her back, she resists. She relents, but Sebastian refuses her, confused about his feelings colliding with his stolid sexuality. Annette flees to the estate of her friend's parents. Sebastian tracks her down, professes his love, and makes love to her. As he has won the bet, Kathryn offers herself to Sebastian the next day, but he refuses; he now only wants Annette. Kathryn tries kissing him, but he rejects her again saying that it's only a stupid bet. She starts taunting him and he tells her he was planning on confessing the truth to Annette anyway. Kathryn warns him not to do it, that people don't change overnight and that it would be destroying not only his reputation, but also hers.

Afterwards, Sebastian full of remorse tells Annette he just wanted to see what she was like in bed. Heartbroken, Annette tells him to leave. He then goes to see Kathryn to fulfill the initial arrangement they had and tells her that he has broken up with Annette and arranged for Cecile and Ronald to be together. Kathryn reveals that she has known all along that he was truly in love with Annette and that it amused her to make him feel ashamed of it. She tells him he gave up on the first person he ever loved, all because she threatened his reputation. Sebastian desperately tries to get a hold of Annette to confess the truth and beg for her forgiveness. Kathryn calls Ronald, telling him that Sebastian slept with Cecile and lying to him that Sebastian hit her. Annette refuses to see or speak to Sebastian, so he leaves his journal for her to read, in which he has detailed all of Kathryn's manipulative schemes as well as their bet, and written his true feelings for Annette. As he heads home, Ronald intercepts him on the street, starting a fight. Annette runs out and tries to stop it, but is accidentally thrown into the way of traffic. Sebastian pushes her to safety, and is hit by a cab. Before dying, Sebastian confesses he loves her and Annette tells him she loves him too. Ronald leaves the scene in shame, realizing Kathryn lied to him.

At Sebastian's funeral, Cecile distributes copies of his journal, made into a book by Annette, titled Cruel Intentions. Kathryn is humiliated and rejected by her classmates and teachers. Her reputation is ruined when cocaine is discovered in her rosary. In the final scene, Annette drives away in Sebastian's car with his journal at her side as she remembers the moments they shared.



Old Westbury Gardens was one of the filming locations

One of the filming locations was Old Westbury Gardens in Nassau County, New York, as well as the Harry F. Sinclair House in New York City.[4]


The film received mixed reviews from critics. Rotten Tomatoes gave the film a score of 52%, based on reviews from 108 critics, with an average score of 5.2/10. The site's consensus stated: "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."[5] Metacritic gave the film an average score of 56% based on reviews from 24 critics.[6] Charles Taylor of described the film as "The dirtiest-minded American movie in recent memory - and an honestly corrupt entertaining picture is never anything to sneeze at."[7] Stephen Holden of The New York Times stated, "You have the queasy sense that the whole thing is just an elaborate stunt, and in this case an exploitative one."[8] Despite this, Roger Ebert—a noted film critic for The Chicago Sun Times—praised Cruel Intentions and gave the film three out of four stars in his review. He stated that it was "smart and merciless in the tradition of the original story".[9]

Cruel Intentions was a commercial success. The film grossed $13,020,565 in its opening weekend, ranking #2 behind Analyze This; released in 2,312 theaters, the movie raked in $75,902,208 worldwide.[1][10]


The film received the following awards and nominations:

Year Ceremony Category Result
2000 Blockbuster Entertainment Awards Favorite Supporting Actress (Reese Witherspoon) Won
Golden Slate Awards Best Original Score Won
Best Actress in a Leading Role (Sarah Michelle Gellar) Nominated
Best Movie Nominated
Best Movie Soundtrack Won
Best Teen Movie Nominated
MTV Movie Awards Best Female Performance (Sarah Michelle Gellar) Won
Best Kiss (Sarah Michelle Gellar, Selma Blair) Won
Best Male Performance (Ryan Phillippe) Nominated
Best Villain (Sarah Michelle Gellar) Nominated
Teen Choice Awards Choice Movie: Drama Won
Choice Movie Actor (Ryan Phillippe) Nominated
Choice Movie Actress (Reese Witherspoon) Nominated
Choice Movie: Love Scene (Reese Witherspoon, Ryan Phillippe) Nominated
Choice Movie: Villain (Sarah Michelle Gellar) Won
Choice Movie: Soundtrack Nominated


The Cruel Intentions soundtrack is a compilation soundtrack released on March 9, 1999 by Arista/Virgin Records. It reached number 60 on the Billboard chart.[citation needed]

The lead track for the film was "Bitter Sweet Symphony" by rock band The Verve.

Prequel and sequels[edit]

The film received two direct-to-video follow-ups: a prequel titled Cruel Intentions 2 in 2001, and a sequel titled Cruel Intentions 3 in 2004. Written and directed by Roger Kumble, the former was assembled from Manchester Prep, a scrapped prequel series by Fox, of which three episodes had been filmed. It features younger versions of the characters of Sebastian Valmont and Kathryn Merteuil played by Robin Dunne and Amy Adams, alongside Sarah Thompson and Keri Lynn Pratt. Cruel Intentions 3 was directed by Scott Ziehl and features Kerr Smith, Kristina Anapau, Nathan Wetherington, Melissa Yvonne Lewis, Natalie Ramsey and Tom Parker.

Cancelled television series[edit]

NBC announced in October 2015 that they had picked up a television pilot for a continuation of the film's storyline. The pilot was to be written by Kumble, Jordan Ross and Lindsey Rosin, with Sebastian Valmont and Annette Hargrove's son being the main character.[11] In February 2016, Taylor John Smith and Samantha Logan were cast, with Smith playing the male lead role of Bash Casey, Sebastian Valmont and Annette Hargrove's son.[12] Gellar reached a deal with producers to reprise her role as the female lead, Kathryn Merteuil.[13] In March, Kate Levering was cast in the role of Annette Hargrove.[14] On October 31, 2016, NBC announced that they decided not to go through with the series.[15]


Cruel Intentions: The Musical is a 1990s jukebox musical also by Ross, Rosin and Kumble, based on the film. After two runs in Los Angeles and a pop-up engagement in New York, the show made its Off-Broadway debut at the Greenwich Village nightclub Le Poisson Rouge in November 2017 and ran into April 2018. Set to pop and rock hits of the 1990s and songs from the film's soundtrack, the plot concern the manipulations of Sebastian Valmont and Kathryn Merteuil. The diabolical step-siblings place a bet on whether or not Sebastian can deflower their incoming headmaster's daughter, Annette Hargrove.[16]


  1. ^ a b c "Cruel Intentions (1999)". Box Office Mojo. Retrieved 2010-03-23.
  2. ^ White, Adam (August 21, 2017). "The cult of Cruel Intentions: how a debauched teen movie seduced a generation". The Daily Telegraph. Retrieved February 18, 2019.
  3. ^ Patti Greco (18 August 2014). "12 Things You Never Knew About Cruel Intentions (Screenwriter and director Roger Kumble shares some trivia about his 1999 movie in an interview with". Cosmopolitan. Retrieved 6 March 2019. [Ryan Philippe]. 'When you break down this movie, it's really about me wanting to have anal sex with my sister.' [When Sebastian and Sarah Michelle's character, Kathryn, make their bet, she says, 'You can put it anywhere.'] I said, 'Well, that's an interesting way of looking at it. I never thought of that.' He's like, 'The whole plot turns on that.' And I go, 'Yeah, it does.' I didn't realize it at the time.
  4. ^ "Cruel Intentions - 1999". Retrieved January 30, 2019.
  5. ^ "Cruel Intentions". Rotten Tomatoes. Retrieved 2011-06-30.
  6. ^ "Cruel Intentions Reviews, Ratings, Credits". Metacritic. Retrieved 2011-06-30.
  7. ^ Taylor, Charles. (1999-03-05). "Cruel Intentions". Retrieved 2014-06-14.
  8. ^ Holden, Stephen. (1999-03-05). "'Cruel Intentions': Back to Their Old Tricks, but a Whole Lot Younger". The New York Times. Retrieved 2011-06-30.
  9. ^ "Cruel Intentions Movie Review (1999)". March 5, 1999. Retrieved January 28, 2015.
  10. ^ Keating, Shannon. "It's Been 20 Years Since "Cruel Intentions," And There's Never Been Another Movie Quite Like It". Buzzfeed News. Retrieved 7 March 2019.
  11. ^ Andreeva, Nellie (February 2, 2016). "'Cruel Intentions' Reboot Gets NBC Pilot Order". Deadline Hollywood. Retrieved February 5, 2016.
  12. ^ Andreeva, Nellie (February 23, 2016). "'Cruel Intentions': Taylor John Smith Set As the Male Lead, Samantha Logan Cast". Deadline Hollywood. Retrieved February 23, 2016.
  13. ^ Andreeva, Nellie (February 24, 2016). "Sarah Michelle Gellar To Reprise 'Cruel Intentions' Role In NBC Pilot". Deadline Hollywood. Retrieved February 25, 2016.
  14. ^ Andreeva, Nellie (March 1, 2016). "'Cruel Intentions': Kate Levering To Play Reese Witherspoon's Annette In NBC Pilot". Deadline Hollywood. Retrieved April 4, 2016.
  15. ^ Andreeva, Nellie (October 31, 2016). "'Cruel Intentions' Not Going Forward At NBC, To Be Shopped Elsewhere By Sony". Deadline Hollywood. Retrieved November 1, 2016.
  16. ^ Lefkowitz, Andy. "Cruel Intentions Musical Extends Off-Broadway Run for Third & Final Time",, February 20, 2018

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