Ryan Phillippe has always been kind of a creepy guy. When he gets cast as weird, unsettling, possibly soulless dudes—which is often—you get the sense that there isn’t much “acting” required. From his dead-eyed shark stare to the soft-spoken murderous speech pattern and the hair that can only be classified as “serial-killer-curls,” it’s always hinted that dude is actually about that life he’s “portraying.”

Fifteen years later, his most infamous sociopath role is still that of Sebastian Valmont, the Upper East Side lady-slaying proto-Chuck Bass scoundrel who sets out to conquer the most unattainable box in his social circle in the '90s teen movie bad-classic Cruel Intentions. He’s a high-level lurk who probably would’ve gone on to become a serial killer, but independent of that, he also happens to be fly as fuck in the most ridiculously over-the-top-'90s-outfits way imaginable. Give props to the Lord Valmont and click through Ryan Phillippe's Most Stylish Creeptastic Moments in Cruel Intentions.

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