Image via Complex Original
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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Lord Valmont eases us into the film in second gear with the basic but still fresh tailored steez. Thirst face already on one hunna.
Ladykiller Sebastian Valmont kicks off the creep-courtship in a shooting jacket, absolutely not a coincidence.
"When I look this damn good I'm in the Harvard club doin' my turn up dance like..."
Please refer to Reese Witherspoon's facial expression. All items are in your shopping cart Mr. Valmont, would you like to checkout?
So creepily excited for this immaculately executed Steve Jobs swagger-jack.
If you're gonna lurk in the cut, come prepared. The shades are a must when hiding out in shorty's room on a sunny day.
Step Goons, reppin that UES-WASP clique.
Young swag gawd Valmont low-key pioneered the All-Black-Everything wave when it came to his personal Cruel Summer.
Dude threw on the brightest shit in his wardrobe, all the better to stand out, while Annette (Reese Witherspoon) glides up the escalator to her impending doom. All done while holding the most serial killer creep pose possible.
Is it a print shirt? A robe? A shirt-robe?! True lords like to keep 'em guessing every once in awhile.
Real creep G's stay swagged up for that late-night "Sup?" text so she knows you don't ever slack.
"Don't front girl, you know it's Ralph tho."
