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, set in New York City among rich high schoolers, is a modern retelling of Pierre Choderlos de Laclos' 1782 novel Les Liaisons dangereuses.

In New York City, wealthy teenager Sebastian Valmont regularly manipulates and seduces women, but seeks someone who poses a challenge to his charm.

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.

As the details of her manipulations, promiscuity, and drug abuse are made public, Kathryn weeps as her reputation and good-girl persona are destroyed.

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.

[9] 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".

"[11] 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".

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.

Cruel Intentions 3 followed in 2004, directed by Scott Ziehl, starring Kerr Smith and Kristina Anapau, as Cassidy Merteuil, cousin to Kathryn.

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.

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.