Cruel Intentions (1999) -

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

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 Cruel Intentions (1999)

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. 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: the headmaster's daughter