Cruel Intentions (1999) (A-Z DELUXE)

Sebastian must seduce and "deflower" the virtuous Annette Hargrove ( Reese Witherspoon ), the headmaster's daughter, who has publicly vowed to remain chaste until marriage.

(1999) is a stylish teen drama that modernizes the 1782 French novel Les Liaisons dangereuses (Dangerous Liaisons) by Pierre Choderlos de Laclos . Set in the elite world of Manhattan prep schools, the film follows two wealthy, manipulative step-siblings, Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont ( Ryan Phillippe ), as they play destructive games with the lives of their peers. The Central Wager

Before his death, Sebastian leaves his journal—which documents all of Kathryn's schemes—to Annette. Annette and Cecile expose the contents at Sebastian's funeral, leading to Kathryn's public disgrace and social ruin. Cruel Intentions (1999)

Sebastian is killed in a traffic accident while trying to save Annette.

If Sebastian succeeds, he wins a night of pleasure with Kathryn, the only girl he cannot have. If he fails, Kathryn gets his prized 1956 Jaguar Roadster. Seduction and Deceit Sebastian must seduce and "deflower" the virtuous Annette

Discover more about the film's production, its origins in 18th-century literature, and its lasting cultural impact through these retrospective reviews and history deep-dives:

Despite mixed reviews upon release, the film became a cult classic, famous for its sharp dialogue, the iconic kiss between Gellar and Blair, and a soundtrack featuring The Verve's "Bitter Sweet Symphony" . The Central Wager Before his death, Sebastian leaves

As Sebastian attempts to woo Annette, Kathryn simultaneously orchestrates the social ruin of a naive freshman, Cecile Caldwell ( Selma Blair ), as revenge against an ex-boyfriend.