Cruel Intentions

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Cruel Intentions
Cruel intentions ver1.jpg
Theatrical release poster
Directed byRoger Kumble
Screenplay byRoger Kumble
Based onLes Liaisons dangereuses
by Pierre Choderlos de Laclos
Produced byNeal H. Moritz
CinematographyTheo van de Sande
Edited by
  • Ryan Mikel
  • Jeff Freeman
Music byEdward Shearmur
Distributed bySony Pictures Releasing
Release date
  • March 5, 1999 (1999-03-05)
Running time
97 minutes
CountryUnited States
  • English
  • French
Budget$10.5 million[1][2]
Box office$75.9 million[1]

Cruel Intentions is a 1999 American teen romantic drama film written and directed by Roger Kumble and starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair. The film is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses, set in New York City among rich high schoolers.[3]

Initially a smaller-budget independent film, it was picked up by Columbia Pictures and widely released March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised and Cruel Intentions has since grossed $76 million worldwide. The box office success spawned a prequel in 2000 and sequel in 2004, as well as a jukebox musical in 2015.

Since its release the film has become regarded as a cult classic.[4][5]


In an upscale New York City mansion, wealthy, popular and intelligent teenager Kathryn Merteuil discusses her private school with Mrs. Caldwell and her daughter, Cecile, who will be starting as a Freshman at the school soon. Kathryn promises Mrs. Caldwell that she will look out for the sheltered, naïve Cecile. When Kathryn's stepbrother Sebastian Valmont enters the room, Mrs. Caldwell reacts to him coldly and leaves with Cecile.

Kathryn tells Sebastian that she intends to use Cecile to take revenge on her ex-boyfriend Court Reynolds, who dumped her for Cecile. Kathryn enlists Sebastian, a notorious womanizer, to seduce Cecile, thereby ruining her in Court's eyes. Sebastian refuses because he is planning to seduce Annette Hargrove, the virgin daughter of the new Headmaster at their school, who has written an essay which was published by a magazine in support of chastity until marriage. After some negotiation, they agree on a wager: if Sebastian fails to seduce Annette, Kathryn gets Sebastian's vintage Jaguar XK140; if he succeeds, Kathryn will have sex with him.

Sebastian's first attempt to seduce Annette fails, as she is apparently already aware of his reputation. Sebastian initially suspects Greg, Annette's friend from Kansas who is a popular football player and closeted homosexual. Sebastian convinces Greg to put in a good word about him to Annette, blackmailing him with a photo of him and Sebastian's openly gay friend in bed. Sebastian also finds out that Mrs. Caldwell was the one who warned Annette about Sebastian. Sebastian finally agrees to corrupt Cecile as revenge. Meanwhile, Cecile confides in Kathryn about her romance with her music teacher, Ronald Clifford. Kathryn reveals this to Mrs. Caldwell, who orders Cecile to end the relationship, but only because Ronald is black. Sebastian lures Cecile to his house by claiming he has a letter to her from Ronald. He then gets Cecile drunk and blackmails her into allowing him to perform oral sex on her. The next day, Cecile confides in Kathryn, who advises her to be as promiscuous as possible to learn how to please Ronald.

Sebastian begins to truly fall in love with Annette, who returns his feelings but is still hesitant. Sebastian calls her a hypocrite for resisting the chance for true love despite claiming that she was waiting for it. Annette finally relents, but Sebastian, confused about his own feelings, now refuses her. Annette flees to the estate of her friend's parents. Sebastian finds her and professes his feelings, and they make love.

Kathryn offers herself to Sebastian after he wins the 'bet', but he rejects her, now only wanting Annette. Sebastian informs Kathryn that he was planning to tell Annette the truth, but a jealous and enraged Kathryn warns him that doing so will destroy both his and Annette's reputations. Sebastian lies to Annette, claiming that she was just a conquest and that he has no real feelings for her. Devastated, Annette tells him to leave. Sebastian informs Kathryn that he has broken up with Annette and now wants his reward for winning the bet. Kathryn reveals that he, not Annette, was the true target of her scheme and that she manipulated him into abandoning Annette for her own amusement. She then dismisses him, telling him that she doesn't sleep with "losers".

Sebastian tries to contact Annette to confess the truth and beg for a second chance, but she refuses to see him. He gives her his journal, in which he has detailed Kathryn's manipulative schemes, their bet, and his true feelings for Annette. Seeking revenge, Kathryn calls Ronald, claiming that Sebastian hurt her and slept with Cecile. Ronald violently confronts Sebastian, and the ensuing fight migrates to the middle of the street. Annette tries to intervene but is thrown into traffic. Sebastian pushes her to safety but ends up getting hit by a taxi. Sebastian and Annette confess their love for each other before he dies. Ronald witnesses this and leaves angry once he finds out from Annette that Kathryn used him.

At Sebastian's funeral, Kathryn delivers a eulogy, which people start leaving midway through. Kathryn rushes outside to find Cecile handing out copies of Sebastian's journal. As the details of her manipulations and drug abuse are made public, Kathryn's reputation is finally destroyed. Feeling guilt over his role in causing Sebastian's death, Ronald writes a detailed confession of how she lied to him about Cecile not being a virgin and her claims about Sebastian hitting her in order to have him killed. It is implied that the disapproving headmaster will expel her from the school, especially after finding cocaine hidden in the cross of her rosary. In the final scene, Annette drives away in Sebastian's car with his journal at her side, recalling their fondest moments together.



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.[6] In a 2016 interview, Sarah Michelle Gellar revealed that the original title of the movie was to be "Cruel Inventions".[7]


Cruel Intentions received mixed reviews from critics. On Rotten Tomatoes, the film has an approval score of 54% based on reviews from 114 critics, with an average rating of 5.20/10. The site's consensus states: "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."[8] Metacritic gave the film an average score of 56 out of 100 based on reviews from 24 critics.[9]

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."[10] 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."[11] 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, stating that it was "smart and merciless in the tradition of the original story."[12]

Box office[edit]

Cruel Intentions was a commercial success, grossing $13,020,565 in its opening weekend, ranking #2 behind Analyze This; released in 2,312 theaters, the movie raked in $76.3 worldwide against a $10.5 million budget.[1][13]

Awards and nominations[edit]

Award Category Nominee(s) Result
Blockbuster Entertainment Awards Favorite Supporting Actress – Drama/Romance Reese Witherspoon Won
Csapnivalo Awards Best Movie Nominated
Best Teen Movie Nominated
Best Movie Soundtrack Nominated
Best Actress in a Leading Role Sarah Michelle Gellar Nominated
Best Original Score Edward Shearmur Won
Golden Trailer Awards Trashiest Trailer Won
MTV Movie Awards Best Male Performance Ryan Phillippe Nominated
Best Female Performance Sarah Michelle Gellar Won
Best Breakthrough Female Performance Selma Blair Nominated
Best Villain Sarah Michelle Gellar Nominated
Best Kiss Sarah Michelle Gellar and Selma Blair Won
Stinkers Bad Movie Awards Worst Remake Nominated
Teen Choice Awards Choice Drama Movie Won
Choice Movie Actor Ryan Phillippe Nominated
Choice Movie Actress Reese Witherspoon Nominated
Choice Movie Sleazebag Sarah Michelle Gellar Won
Ryan Phillippe Nominated
Choice Movie Hissy Fit Nominated
Choice Sexiest Love Scene Ryan Phillippe and Reese Witherspoon Nominated
Choice Movie Soundtrack Cruel Intentions Nominated
Vega Digital Awards Social Campaigns Won


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

Subsequent media[edit]

Direct-to-video films[edit]

Cruel Intentions 2 was released direct-to-video in 2001, written and directed by Roger Kumble, assembled from three episodes filmed for Manchester Prep, a prequel series scrapped by Fox. The story features younger versions of Sebastian Valmont and Kathryn Merteuil played by Robin Dunne and Amy Adams.

Cruel Intentions 3 followed in 2004, directed by Scott Ziehl, starring Kerr Smith and Kristina Anapau, as Cassidy Merteuil, cousin to Kathryn.

Canceled sequel 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 set seventeen years after the events of the film and sees Bash Casey, son of Sebastian Valmont and Annette Hargrove, discover his late father's journal. Upon discovering this he is thrown into a world of lies, sex and power. The potential series will also see Kathryn Merteuil, Bash's step-aunt, attempt to gain power of Valmont International.[15]

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.[16] Gellar reached a deal with producers to reprise her role as the female lead, Kathryn Merteuil.[17] In March, Kate Levering was cast to replaces Witherspoon for the role of Annette Hargrove.[18]

On October 31, 2016, NBC announced that it had passed on the project and that the series would not go forward.[19]

Planned reboot series[edit]

In October 2021, it was announced that a television series reboot of Cruel Intentions was in development for IMDb TV (now Amazon Freevee).[20][21][22]


A 1990s jukebox musical by Kumble, Rosin, and Ross, was first staged in 2015. After two runs in Los Angeles and a pop-up engagement in New York, Cruel Intentions: The '90s Musical made its Off-Broadway debut at the Greenwich Village nightclub Le Poisson Rouge in November 2017 and ran through April 2018. Set to pop and rock hits of the 1990s and songs from the film's soundtrack, the plot follows the manipulations of Sebastian Valmont and Kathryn Merteuil, out to destroy anyone who gets in their way.[23]


  1. ^ a b c "Cruel Intentions (1999)". Box Office Mojo. Retrieved March 27, 2019.
  2. ^ "The Fault in Our Stars (2014)". The Numbers. Nash Information Services, LLC. Archived from the original on September 18, 2016. Retrieved August 10, 2016.
  3. ^ White, Adam (August 21, 2017). "The cult of Cruel Intentions: how a debauched teen movie seduced a generation". The Daily Telegraph. Archived from the original on January 12, 2022. Retrieved February 18, 2019.
  4. ^ Brackett, Charmain (April 17, 2019). "Cruel Intentions is cult classic now made for stage". The Augusta Chronicle. Retrieved April 9, 2022.
  5. ^ Heller, Corinne; Lubitz, Spencer (September 18, 2021). "How Ryan Phillippe Really Feels About His Kids Watching Cruel Intentions". E!. Retrieved April 9, 2022.
  6. ^ "Cruel Intentions – 1999". Retrieved January 30, 2019.
  7. ^ "Sarah Michelle Gellar reveals original title of 'Cruel Intentions' movie". The Indian Express. February 27, 2016. Retrieved November 16, 2020.
  8. ^ "Cruel Intentions". Rotten Tomatoes. Retrieved March 30, 2022.
  9. ^ "Cruel Intentions Reviews, Ratings, Credits". Metacritic. Retrieved June 30, 2011.
  10. ^ Taylor, Charles. (March 5, 1999). "Cruel Intentions". Retrieved 2014-06-14.
  11. ^ Holden, Stephen. (March 5, 1999). "'Cruel Intentions': Back to Their Old Tricks, but a Whole Lot Younger". The New York Times. Retrieved 2011-06-30.
  12. ^ "Cruel Intentions Movie Review (1999)". March 5, 1999. Retrieved January 28, 2015.
  13. ^ Keating, Shannon. "It's Been 20 Years Since "Cruel Intentions," And There's Never Been Another Movie Quite Like It". Buzzfeed News. Retrieved March 7, 2019.
  14. ^ "Billboard 200 – The Week of March 27, 1999". Billboard. January 2, 2013. Retrieved June 18, 2019.
  15. ^ Andreeva, Nellie (February 2, 2016). "'Cruel Intentions' Reboot Gets NBC Pilot Order". Deadline Hollywood. Retrieved February 5, 2016.
  16. ^ Andreeva, Nellie (February 23, 2016). "'Cruel Intentions': Taylor John Smith Set As the Male Lead, Samantha Logan Cast". Deadline Hollywood. Retrieved February 23, 2016.
  17. ^ Andreeva, Nellie (February 24, 2016). "Sarah Michelle Gellar To Reprise 'Cruel Intentions' Role In NBC Pilot". Deadline Hollywood. Retrieved February 25, 2016.
  18. ^ Andreeva, Nellie (March 1, 2016). "'Cruel Intentions': Kate Levering To Play Reese Witherspoon's Annette In NBC Pilot". Deadline Hollywood. Retrieved April 4, 2016.
  19. ^ Andreeva, Nellie (October 31, 2016). "'Cruel Intentions' Not Going Forward At NBC, To Be Shopped Elsewhere By Sony". Deadline Hollywood. Retrieved November 1, 2016.
  20. ^ Lutkin, Aimee (October 2, 2021). "Cruel Intentions Is Rebooting as a TV Show In the Scandalous World of Politics". Elle. Retrieved April 9, 2022.
  21. ^ Andreeva, Nellie (October 1, 2021). "Cruel Intentions Series Reboot In Works at IMDb TV". Deadline Hollywood. Retrieved April 9, 2022.
  22. ^ Waite, Thom (October 2, 2021). "Cruel Intentions is set to be rebooted as a TV series set in Washington DC". Dazed. Retrieved April 9, 2022.
  23. ^ Lefkowitz, Andy. "Cruel Intentions Musical Extends Off-Broadway Run for Third & Final Time",, February 20, 2018

External links[edit]