While Sebastian pursues Annette, Kathryn executes her own revenge plot against her ex-boyfriend by manipulating an innocent girl, Cecile Caldwell (Selma Blair). Ms. Magazine Annette's Influence:

Cruel Intentions (1999) is an American teen drama film directed by Roger Kumble, adapted from the 1782 French novel Les Liaisons Dangereuses by Pierre Choderlos de Laclos. Set among wealthy Manhattan teenagers, the film follows step-siblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe) as they manipulate and seduce peers for sport. A central wager involves Sebastian’s attempt to seduce the virtuous Annette Hargrove (Reese Witherspoon), which leads to emotional consequences that upend the characters’ power dynamics.

Cult Classic / Genre Definitive / Essential 90s Cinema

"Cruel Intentions" is a thought-provoking film that explores the complexities of adolescent relationships, power dynamics, and social class. Through its nuanced characters and commentary on societal norms, the movie offers a critical analysis of the human experience. As a cultural artifact, "Cruel Intentions" remains relevant today, serving as a cautionary tale about the dangers of manipulation and the importance of empathy.

The performances are top-notch, with standout moments from Ryan Phillippe and Sarah Michelle Gellar, who bring depth and nuance to their characters.

| | Role | |-----------|----------| | Sarah Michelle Gellar | Kathryn Merteuil | | Ryan Phillippe | Sebastian Valmont | | Reese Witherspoon | Annette Hargrove | | Selma Blair | Cecile Caldwell | | Louise Fletcher | Helen Rosemond (Annette’s aunt) | | Joshua Jackson | Blaine Tuttle | | Eric Mabius | Greg McConnell |

One of the most talked-about moments in teen cinema history is the scene between Kathryn and Cecile Caldwell (Selma Blair), which won "Best Kiss" at the 2000 MTV Movie Awards.

: As Sebastian spends time with Annette, his cynical exterior begins to crack. For the first time, he experiences genuine love, causing him to question his manipulative lifestyle.

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