Cruel Intentions

In an upscale New York City mansion, wealthy and popular teenager Kathryn Merteuil discusses her prep school with Mrs. Caldwell and her daughter, Cecile. Kathryn promises Mrs. Caldwell that she will look out for the naive 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-lover Court Reynolds, who dumped her for Cecile. Kathryn asks Sebastian to seduce Cecile, thereby spoiling her in Court's eyes. Sebastian refuses because he is planning to seduce Annette Hargrove, the headmaster's virgin daughter, who has published an essay 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, suggesting possibility of anal as well, since Kathryn is the only girl Sebastian has failed to bed.

Sebastian's first attempt to seduce Annette fails, as she already knows about his bad reputation. Sebastian discovers that Mrs. Caldwell, Cecile's mother, warned Annette about him. He finally agrees to corrupt Cecile out of revenge.

Meanwhile, Cecile confides in Kathryn about her romance with her same age music teacher, Ronald Clifford. Kathryn reveals the romance to Mrs. Caldwell, who orders Cecile to end the relationship, her disapproval arising out of his race. Sebastian lures Cecile to his house, offering a letter from Ronald. He then gets Cecile drunk and blackmails her in order to trick 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 because although she claims to be waiting for her one true love, she resists him when he chooses to love her back. 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 love, and they consummate their relationship.

Kathryn offers herself to Sebastian after he wins the 'bet', but he rejects her: he now only wants Annette. Enraged and jealous, Kathryn insults his masculinity. Stung, Sebastian informs her that he was planning to tell Annette the truth. Kathryn warns him that doing so will destroy both his and Annette's reputations. Sebastian lies to Annette, claiming he just wanted to see what she was like in bed, 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, and not Annette, was the true victim of her scheme: for her own amusement, she manipulated him into abandoning Annette once she realized that he truly loved her. She then dismisses him, telling him that she doesn't sleep with "losers."

Sebastian desperately tries to contact Annette to confess the truth and beg her forgiveness, 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.

Ronald starts a fist fight with Sebastian after Kathryn tells him that Sebastian hit her and violated Cecile. Annette tries to intervene, but is thrown into traffic; Sebastian is hit by a car when he pushes her to safety. Before dying, Sebastian confesses his love for her and Annette tells him she loves him too. Ronald leaves the scene in shame, realizing Kathryn manipulated him.

In her eulogy at Sebastian's funeral, Kathryn claims she tried to set an example for her late brother. When people start leaving midway through her speech, 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 and it is implied that the disapproving headmaster will expel her from the school.

In the final scene, Annette drives away in Sebastian's car with his journal at her side, remembering the good moments they shared 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 notably 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

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.[5]

The film received mixed reviews from critics. Rotten Tomatoes gave the film a score of 54%, based on reviews from 114 critics, with an average score of 5.26/10. 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."[6] Metacritic gave the film an average score of 56% based on reviews from 24 critics.[7] 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."[8] 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."[9] 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."[10] 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][11]

The movie was nominated for Worst Remake at the 1999 Stinkers Bad Movie Awards, but lost to The Haunting.[12]

The film received the following awards and nominations:

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

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, Cruel Intentions 2 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.

Wikiquote has quotations related to: Cruel Intentions

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