Peak Sexy: Ryan Phillippe Makes Sociopathy Seem Seductive In ‘Cruel Intentions’

To be a movie star, you’ve gotta have that thing — that combination of charisma, charm, and, above all else, sexiness. Each week in this column, we’ll look back at an actor’s role when they were in their prime. When they were the hottest thing in Hollywood. When they were Peak Sexy. This week, we celebrate Ryan Phillippe in the teen drama, Cruel Intentions.

There was one extremely important actor who was fundamental to those of us who came of age in the late ’90s and struggled with emotional and sexual feelings we did not understand. Yes, that actor was Ryan Phillippe.

While he first caught attention on One Life to Live, playing the first gay teenager on a soap opera, and he appeared in small roles in White Squall and Crimson Tide (just imagine being stuck on a boat with him, jeeez), but he really hit his stride as a hearthrob toward the end of the decade, making his breakthrough role in the 1997 slasher flick I Know What You Did Last Summer. Do you remember him waltzing around in that tank top? What a hot dirtbag, seriously. The following year he even got a starring role in Mark Christopher’s much-maligned 54, which featured the very important scene of young Ryan Phillippe ripping off his shirt in order to get into the infamous disco.

While both of those Ryan Phillippes were certainly hot, I’m willing to go on record and say that his most important role — at least in my own sexual development, and this is really more about me here — is that of Sebastian Valmont in the modern-day retelling of Pierre Choderlos de Laclos’ classic novel Les Liaisons dangereuses. Cruel Intentions brought a new spin to the tale, which had previously seen adaptations in the Oscar-winning Dangerous Liaisons and the less critically acclaimed Valmont. Roger Kumble’s reimagining of Laclos’ bawdy tale of cruelly manipulative aristocrats set the sexual shenanigans within the exclusive set of Manhattan’s teenage upper crust.

First of all, Sebastian’s a total prick, which probably is part of his appeal. I mean, it certainly isn’t the N*SYNC-era Timberlake curls he’s sporting, or the chunky turtleneck sweaters that look like they were pulled from a sale rack at Structure. No, it’s the attitude, the obsessive nature of his vindictiveness, his overwhelming desire to fuck his step-sister Kathryn Merteuil (played by a perfectly devilish Sarah Michelle Gellar) that he’ll go out of his way to seduce (poor thing) the angelic prude Annette Hargrove (Reese Witherspoon, in the role that saw her shirk off her previous sexpot image seen in movies like Pleasantville and Freeway and rebrand her as the girl next door).

Oh, and there was that pool scene.

LOOK AT THAT BUTT. THAT’S THE WORLD’S MOST PERFECT BUTT.

The most magical thing, of course, is that its attached to a rich jerk. A cherubic rich jerk. A rich jerk who doesn’t care about your feelings but will toy with them nonetheless. He’s the kind of rich jerk who manages to be less than threatening for a questioning young sixteen-year-old, who may not understand human behavior when it comes to emotional relationships, but can still recognize a perfect butt when he sees one.

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Photos: Columbia Pictures