Cruel Intentions

Initially a smaller-budget independent film, it was picked up by Columbia Pictures and widely released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised and the film grossed $76 million worldwide. Its 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.^[3][4]

Plot[edit]

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 highway in Sebastian's car while wearing his sunglasses and with his journal at her side, recalling their fondest moments together.