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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. 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. Plot 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. Cast 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 Production 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. In a 2016 interview, Sarah Michelle Gellar revealed that the original title of the movie was to be "Cruel Inventions". Reception 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". Metacritic gave the film an average score of 56 out of 100 based on reviews from 24 critics. 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". 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." Roger Ebert of The Chicago Sun-Times praised Cruel Intentions and gave the film three out of four stars in his review, s.... Discover the Annette Blair popular books. Find the top 100 most popular Annette Blair books.