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Step-siblings Sebastian and Kathryn make a bet of the former bedding the headmaster's daughter, Annette. However, in an unexpected turn of events, Sebastian falls truly in love with Annette.
Initial release: 5 March 1999 (USA)
Director: Roger Kumble
Featured song: Bitter Sweet Symphony
Film series: Cruel Intentions
Awards: MTV Movie Award for Best Kiss, Teen Choice Award for Film - Choice Sleazebag
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