Cruel Intentions

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 an adaptation of the novel Les Liaisons dangereuses, written by Pierre Choderlos de Laclos in 1782, but set among wealthy teenagers attending high school in New York City instead of 18th-century France.

The film started as a smaller budget independent film, but was picked up by Columbia Pictures and released on March 5, 1999. Despite mixed critical reviews, the performances of Gellar, Philippe, and Witherspoon were praised. Cruel Intentions was a box office success, earning $76 million, with two direct-to-video sequels.

Plot
In an upscale New York City mansion, wealthy and popular girl 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 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, as 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 music teacher, Ronald Clifford. Kathryn reveals the romance to Mrs. Caldwell, who orders Cecile to end the relationship. Sebastian lures Cecile to his house, offering a letter from Ronald. He then blackmails Cecile in order to perform oral sex on her. The next day, Cecile confides in Kathryn, who advises her to be as promiscuous as possible 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, but has no real feelings for her. Devastated, Annette tells him to leave.

Sebastian informs Kathryn that he has broken 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. Kathryn's spotless reputation is finally destroyed as the details of her manipulations are made public, and it’s hinted that she gets expelled from school and possibly arrested for the death of Sebastian due to her lies that started the whole thing.

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

Cast

 * Sarah Michelle Gellar as Kathryn Merteuil, based on the Marquise de Merteuil
 * Ryan Phillippe as Sebastian Valmont, based on the Viscomte de Valmont
 * Reese Witherspoon as Annette Hargrove, based on Madame de Tourvel
 * Selma Blair as Cecille 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 Marcie 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.

Reception
The film received mixed reviews from critics. Rotten Tomatoes gave the film a score of 54%, based on reviews from 113 critics, with an average score of 5.24/10. 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." Metacritic gave the film an average score of 56% 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 stated, "You have the queasy sense that the whole thing is just an elaborate stunt and, in this case, an exploitative one." 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." 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.

Awards
The film received the following awards and nominations:

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

Prequel and sequels
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, respectively, 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.

Cancelled television series
NBC announced in October 2015 that they had picked up a television pilot for a continuation of the film's storyline, which was to be written by Kumble, Jordan Ross and Lindsey Rosin, with Sebastian Valmont and Annette Hargrove's son being the main character. 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. Gellar reached a deal with producers to reprise her role as the female lead, Kathryn Merteuil. In March, Kate Levering was cast in the role of Annette Hargrove. On October 31, 2016, NBC announced that they decided not to go through with the series.

Musical
Cruel Intentions: The Musical is a 1990s jukebox musical also by Ross, Rosin and Kumble, based on the film. After two runs in Los Angeles and a pop-up engagement in New York, the show 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 concern the manipulations of Sebastian Valmont and Kathryn Merteuil. The diabolical step-siblings place a bet on whether or not Sebastian can deflower their incoming headmaster's daughter, Annette Hargrove.