Cruel Intentions
A sharp, seductive update of Laclos' 1782 novel Les Liaisons dangereuses transplanted to Manhattan's prep-school elite, starring Sarah Michelle Gellar and Ryan Phillippe. Written and directed by Roger Kumble, it became a defining late-90s teen drama with genuine cultural impact.
Released on March 5, 1999, Cruel Intentions transplants the manipulative scheming of Pierre Choderlos de Laclos' classic epistolary novel into the world of Manhattan's Upper East Side private schools. Gellar stars as the ruthless Kathryn Merteuil—cocaine vial hidden in the crucifix she carries—Phillippe as the charming Sebastian Valmont, with Reese Witherspoon as Annette Hargrove and Selma Blair as Cecile Caldwell rounding out the ensemble of wealthy, morally compromised teenagers.
The film's most iconic moment became the passionate kiss between Gellar and Blair, which won Best Kiss at the 2000 MTV Movie Awards. The film's ending scene plays out to The Verve's "Bitter Sweet Symphony," and that licensing decision nearly defined the film's finances: securing the rights to the song cost approximately $1 million—roughly 10 percent of the entire $10.5 million budget—partly due to residual litigation involving the Rolling Stones' former manager Allen Klein. On that investment, the film grossed $75.9 million worldwide, proving that audiences were hungry for teen stories with literary pedigree and moral complexity.
Off-screen, the release marked a romantic turning point: Phillippe and Witherspoon were already a couple, having met at Witherspoon's 21st birthday party in March 1997—not on the set of this film, despite later assumptions—and married in June 1999, just three months after the film's release. The property's longevity extended to direct-to-video sequels and a 2024 Amazon series that revisited the same world and characters, testament to the original's enduring appeal.
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