Release Date
March 5, 1999
Roger Kumble
Roger Kumble
Distributed By
Columbia Pictures
$10.5 million
Drama, Romance, Thriller
Rated R for strong sexual dialogue and sexual situations involving teens, language and drug use
97 minutes

Cruel Intentions

Few films have ever matched the dynamic of Cruel Intentions. Sure, the name is now synonymous with countless sequels the likes of the franchise Wild Things, coming close to becoming X-rated versions of their predecessors, but the original film contained a class and sophistication that neither of the sequels could possibly match.

Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon would probably not be the famous names that they are today without this first legitimate venture under their belts. Sarah Michelle Gellar plays the sexy but evil temptress Kathryn, playing the role of the Catholic school student body leader, then turning around and snorting coke out of her cross necklace. Kathryn’s step-brother, the suave and debonaire Sebastian (Ryan Phillippe) struggles with the line between his reputation of being the city’s biggest ladies’ man and the developing “good guy” that works him over for the chaste and virtuous Annette. Through a bet between the step-siblings, Sebastian finds that choosing between love and lust can be more difficult than it appears.

Reese Witherspoon was never more vivacious and completely embodies the perfect woman in Annette Hargrove. Her sophisticated speech mixed with her unwillingness to fall for Sebastian’s arsenal of sexual games makes her a woman worth fighting for. Absolutely none of Witherspoon’s performances following or prior have ever matched the character of Annette, as she cracks open the apparent hollow shell of Sebastian. Contrast Annette with the dimwitted Cecile (Selma Blair) who folds to every one of Sebastian’s sexual advances and becomes utterly unattractive, and reinstating Annette as the culmination of every man’s sexual desires.

The film screams sex, but in a honorable and tasteful way. Cruel Intentions is just what the title suggests and earns its ‘R’ rating. However, this film screams classic, matching the likes of Varsity Blues and 10 Things I Hate About You. These films signify a generation and delivers a nostalgic feel when viewing each one of them more than a decade later.

The twisting story of Cruel Intentions comes from a French epistolary novel Les Liaisons dangereuses and rivals a Greek tragedy with the many levels of relationships occurring simultaneously, on screen and off screen. This dynamic also brings out all different relationship types: heterosexual relationships, homosexual relationships, the sexual desire between step-siblings, the couples that want to wait until marriage, couples that have to hide their relationships, and the relationship between a mother and daughter. All of this encompasses the story of the film and creates a truly original piece of American cinema.

Cruel Intentions missed any sort of Academy success, but the commercial success was far superior to anything out at the time. Garnering multiple Teen Choice and MTV awards, the proof that this film represents a generation is difficult to argue.

Filled with breakthrough performances still representing these actors and actresses to this day and introducing sexual discovery to a generation over a decade ago, Cruel Intentions continues to carry its same weight today without falling into the oldie, but goodie pile, remaining a pop-culture icon. Though the iconic image of the film was Sarah Michelle Gellar and Selma Blair sharing a passionate kiss, the film reaches far further than just shock value and becomes one of the most memorable films from that generation and for that generation.


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