In New York City, wealthy teenager Sebastian Valmont regularly manipulates and seduces women, but wants to find someone who poses a challenge to his charm. He settles on Annette Hargrove, the daughter of his new school headmaster, who is staunchly opposed to sex before falling in love. Sebastian and his equally manipulative step sister, the intelligent and popular Kathryn Merteuil, agree to a bet: if Sebastian fails to seduce Annette then Kathryn gets his vintage Jaguar XK140; if he wins Kathryn will finally have sex with him. Kathryn tries to recruit Sebastian into her own scheme to take revenge on her ex-boyfriend Court Reynolds, who left her because of her promiscuity and began dating the naive and innocent Cecile Caldwell.

Sebastian's initial efforts to seduce Annette fail as she has been informed of his reputation. He suspects Annette's friend Greg, a popular footballer and closeted homosexual, and blackmails him into convincing Annette he is a good person. Sebastian also learns that it was Cecile's mother that warned Annette and agrees to corrupt Cecile as revenge. Kathryn notices romantic tension between Cecile and her young music teacher Ronald Clifford and reveals this to Cecile's mother, who fires Ronald. Sebastian and Kathryn convince Ronald to fight for Cecile by writing her a love letter which Sebastian uses to lure Cecile to his bedroom, where he blackmails her into receiving oral sex from him. The next day, Kathryn advises Cecile to have sex with Sebastian and be as promiscuous as possible so she can please Ronald.

Spending time with Annette, Sebastian develops genuine feelings for her, attracted to her honesty and ability to make the normally stoic Sebastian laugh. He kisses Annette but she resists because she also has feelings for him and fears she cannot restrain herself around him. Sebastian calls her a hypocrite for rejecting the opportunity for true love and she finally relents and begins undressing, but Sebastian, confused about his own feelings, declines to have sex with her. Annette leaves the following day but Sebastian finds her, professes his feelings, and they have sex.

A jealous Kathryn tries to seduce Sebastian, but is frustrated that her hold over him has been broken by his feelings for Annette, and she convinces him that he cannot change his true nature. Sebastian plans to tell Annette the truth about the bet but Kathryn warns him that he will only destroy both his and Annette's reputations. He meets with Annette and lies to her, claiming he only wanted to have sex with her and has no real feelings for her. Devastated, Annette tells him to leave. Sebastian tells Kathryn that he has broken up with Annette and now wants his reward for winning the bet but she dismisses him. Kathryn reveals that he was the true target of her scheme and that she manipulated him into feeling shame over his love for Annette for her own amusement.

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 and though Sebastian pushes her to safety, he is struck by a taxi. Sebastian and Annette confess their love for each other before he dies.

At Sebastian's funeral, Kathryn, unmoved by Sebastian's death, delivers a eulogy, but people start leaving while she is still speaking. Kathryn rushes outside to find Cecile handing out copies of Sebastian's journal, titled Cruel Intentions. As the details of her manipulations, promiscuity, and drug abuse are made public, Kathryn weeps as her reputation and good-girl persona are destroyed. Annette drives down a higway in Sebastian's car while wearing his sunglasses and with his journal at her side, recalling their fondest moments together.

• Sarah Michelle Gellar as Kathryn Merteuil, based on the Marquise de Merteuil
• Ryan Phillippe as Sebastian Valmont, based on the Vicomte de Valmont
• Reese Witherspoon as Annette Hargrove, based on Madame de Tourvel
• Selma Blair as Cecile Caldwell, based on Cécile Volanges
• Louise Fletcher as Helen Rosemond, based on Madame de Rosemonde
• Joshua Jackson as Blaine Tuttle
• Eric Mabius as Greg McConnell
• Sean Patrick Thomas as Ronald Clifford, based on the Chevalier Danceny
• Swoosie Kurtz as Dr. Regina Greenbaum (Kurtz portrayed Madame de Volanges in the 1988 film version of Dangerous Liaisons)
• Christine Baranski as Bunny Caldwell, based on Madame de Volanges
• Alaina Reed Hall as Nurse
• Deborah Offner as Mrs. Michalak
• Tara Reid as Marci Greenbaum
• Hiep Thi Le as Mai-Lee
• Herta Ware as Mrs. Sugarman
• Drew Snyder as Headmaster Hargrove
• Charlie O'Connell as Court Reynolds, based on the Comte de Gercourt
• Fred Norris as Meter Maid

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.^[5] In a 2016 interview, Sarah Michelle Gellar revealed that the original title of the movie was to be "Cruel Inventions".^[6]

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".^[7] Metacritic gave the film an average score of 56 out of 100 based on reviews from 24 critics.^[8]

Charles Taylor of Salon.com described the film as "the dirtiest-minded American movie in recent memory – and an honestly corrupt entertaining picture is never anything to sneeze at".^[9] Stephen Holden of The New York Times wrote: "You have the queasy sense that the whole thing is just an elaborate stunt and, in this case, an exploitative one."^[10] Roger Ebert of 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".^[11]

Box office edit

Cruel Intentions was a commercial success, grossing $13,020,565 in its opening weekend, ranking No. 2 behind Analyze This; released in 2,312 theaters, the movie raked in $76.3 worldwide against a $10.5 million budget.^[1][12]

Awards and nominations edit

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.^[17] The lead track for the film was "Bitter Sweet Symphony" by rock band The Verve.

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.

None of the cast from the original appeared in the sequels.

Canceled sequel series edit

NBC picked up a television pilot for a continuation of the film's storyline in October 2015. 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 was to have Kathryn Merteuil, Bash's step-aunt, attempt to gain power of Valmont International.^[18]

Four months later in February, 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.^[19] Gellar reached a deal with producers to reprise her role as the female lead, Kathryn Merteuil.^[20] In March, Kate Levering was cast to replace Witherspoon for the role of Annette Hargrove.^[21]

Several months later, on October 31, NBC passed on the project and the series did not go forward.^[22]

Planned reboot series edit

As of October 2021, a television series reboot of Cruel Intentions was in development for IMDb TV (now Amazon Freevee).^[23][24][25] In April 2023, the reboot was given a series order.^[26]

Musical edit

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.^[27]

• Blonde versus brunette rivalry^[28]
• Wild Things

• Cruel Intentions at IMDb  
• Cruel Intentions at AllMovie  
• Cruel Intentions at Box Office Mojo  
• Cruel Intentions at Metacritic  
• Cruel Intentions at Rotten Tomatoes