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Movie Rewind: Cruel Intentions

Most contemporary films set in modern day society often reflect the values and views of our culture at that point in time. If you look at the flicks of the 70s, 80s, or even 90s, you can notice particular styles, images, music, beliefs, and technology that only pertain to the zeitgeist of American culture at the very moment its being depicted.

Which must mean that in 1999, American teenagers were a bunch of spoiled, sneaky, rich, incestual sluts.

At least, that’s what I believe Cruel Intentions sets out to prove. A sign-of-the-times which featured the sexiest young adult cast possible: Ryan Phillppe, Sarah Michele Gellar, Joshua Jackson, Selma Blair, Alicia Silverstone, Sean Patrick Thomas, and Tara Reid as posh private school devils who spin a web of sexual betrayal, starring Phillippe and Gellar as two stepsiblings who do everything in their power to ruin the lives of those around them in order to achieve their ultimate sexual desires.

There’s the prissy Ryan Phillippe as Sebastian, a scheming brat whose first scene entails screwing over his therapist by posting nude shots of her daughter (the then-unknown Tara Reid) on the internet (Microsoft Internet Explorer for Windows 95). Sebastian’s a womanizing sex God who’s grown tired of the usual conquests (“I’m sick of sleeping with these insipid Manhattan debutantes!”) wants to lay the most virtuous virgin on the planet, Annette (Alicia Silverstone), and Sarah Michelle Gellar as Kathryn – whose sinful spirit hides neatly behind an aura of elegance peppered with an coquettishly arrogant tone, plans to deflower the innocence of young Cecile (Selma Blair), whose boyfriend just happens to be an ex of hers. The true grit lies in the guilty sexual attraction between Sebastian and Kathryn, stepsiblings who’d just as easily bang each other’s brains out.

So Kathryn makes the wager: if she corrupts Cecile’s virginity before Sebastian can get to Annette, then she gets his car. If Sebastian can lay the headmaster’s daughter first, then he gets to have his stepsister Kathryn any way he wants her (“In English? I’ll f*ck your brains out.”) The resulting hour is a tantalizing spin of sex, lies, lesbian kisses, all on the potential promise of anal sex. Kathryn prepares Cecile to bump uglies with her music teacher Ronald (Sean Patrick Thomas), while Sebastian faux-woos Annette. The unexpected wrench in the plan: thanks to the thrill of the chase, Sebastian actually starts to fall in love with the girl, who still keeps her guard up. The resulting finish is a sprawling contraption of blackmail and betrayal that is just as good to observe 12 years later.

While Cruel Intentions was nothing too special in critics’ eyes, many of whom panned it for its sharply malicious and sex-charged nature. Let’s just run through a brief timeline: 22 minutes before Sarah Michelle Gellar and Selma Blair suck face. Just five minutes later, we’re staring at a skinny-dipping Phillippe’s bare ass. The direct next scene, we’re walking in on gay sex. Like it or not, that’s pretty much the ebb and flow of the film. But somehow, watching stepsiblings take their sweet time sexually arousing is two parts repulsive and three parts magicially delicious. Despite its dirty nature, the context and depravity of Cruel Intentions is exactly what’s made it a cult classic.

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