# Cruel Intentions

Cruel Intentions is a 1999 American teen romantic drama film written and directed by Roger Kumble, and starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon, and Selma Blair. The film, set in New York City among rich high schoolers, is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses.
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. Since its release, the film has become regarded as a cult classic.
Its box office success spawned a media franchise with a prequel in 2000 and a sequel in 2004, as well as a jukebox musical in 2015 and a 2024 television series.

## Plot

In New York City, wealthy teenager Sebastian Valmont regularly manipulates and seduces women, but seeks 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 stepsister, 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 closeted homosexual, of being responsible and blackmails him into convincing Annette of his good nature. Sebastian also learns that Cecile's mother 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 devastates Annette by lying that he only wanted her for sex and feels nothing for her. Sebastian tells Kathryn that he has broken up with Annette and, having won the bet, wants his reward, 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 Sebastian is fatally wounded pushing her to safety. Sebastian and Annette confess their love for each other before he dies.
At Sebastian's funeral, Kathryn, unmoved by Sebastian's death, begins to deliver a eulogy, but people leave before she can finish. 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
* Hiep Thi Le as Mai-Lee
* Deborah Offner as Mrs. Michalak
* Tara Reid as Marci Greenbaum
* Drew Snyder as Headmaster Hargrove
* Herta Ware as Mrs. Sugarman
* 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 "Cruel Inventions".

## Reception

On Rotten Tomatoes, Cruel Intentions has an approval score of 54% based on 119 reviews, with an average rating of 5.20/10. The site's critics 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 a weighted average score of 56 out of 100 based on 24 critics, indicating "mixed or average reviews". Audiences polled by CinemaScore gave the film an average grade of "B-" on an A+ to F scale.
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, stating that it was "smart and merciless in the tradition of the original story".

### Box office

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.

### Awards and nominations

| Award | Category | Nominee(s) | Result |
| Blockbuster Entertainment Awards | Favorite Supporting Actress – Drama/Romance | Reese Witherspoon | Won |
| Csapnivalo Awards | Best Movie | Best Movie | Nominated |
| Csapnivalo Awards | Best Teen Movie | Best Teen Movie | Nominated |
| Csapnivalo Awards | Best Movie Soundtrack | Best Movie Soundtrack | Nominated |
| Csapnivalo Awards | Best Actress in a Leading Role | Sarah Michelle Gellar | Nominated |
| Csapnivalo Awards | Best Original Score | Edward Shearmur | Won |
| Golden Trailer Awards | Trashiest Trailer | Trashiest Trailer | Won |
| MTV Movie Awards | Best Male Performance | Ryan Phillippe | Nominated |
| MTV Movie Awards | Best Female Performance | Sarah Michelle Gellar | Won |
| MTV Movie Awards | Best Breakthrough Female Performance | Selma Blair | Nominated |
| MTV Movie Awards | Best Villain | Sarah Michelle Gellar | Nominated |
| MTV Movie Awards | Best Kiss | Sarah Michelle Gellar and Selma Blair | Won |
| Stinkers Bad Movie Awards | Worst Remake | Worst Remake | Nominated |
| Teen Choice Awards | Choice Drama Movie | Choice Drama Movie | Won |
| Teen Choice Awards | Choice Movie Actor | Ryan Phillippe | Nominated |
| Teen Choice Awards | Choice Movie Actress | Reese Witherspoon | Nominated |
| Teen Choice Awards | Choice Movie Sleazebag | Sarah Michelle Gellar | Won |
| Teen Choice Awards | Choice Movie Sleazebag | Ryan Phillippe | Nominated |
| Teen Choice Awards | Choice Movie Hissy Fit | Ryan Phillippe | Nominated |
| Teen Choice Awards | Choice Sexiest Love Scene | Ryan Phillippe and Reese Witherspoon | Nominated |
| Teen Choice Awards | Choice Movie Soundtrack | Cruel Intentions | Nominated |
| Vega Digital Awards | Social Campaigns | Social Campaigns | Won |

## 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.

## Subsequent media
### Direct-to-video films

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, respectively.
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

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.
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 to replace Witherspoon for the role of Annette Hargrove.
Several months later, on October 31, NBC passed on the project and the series did not go forward.

### Amazon Prime Video reboot series

In October 2021, a television series reboot of Cruel Intentions was in development for IMDb TV (now Amazon Freevee). In April 2023, the reboot was given a series order. It premiered on Amazon Prime Video on November 21, 2024.

### Musical

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.