You Aren't the Only One With a Complicated Crush on Sebastian Valmont

There's "bad boy," and then there's whatever you'd call Ryan Phillippe's character in Cruel Intentions. In honor of Phillippe's birthday on Saturday, we're taking a look back at one of Phillippe's most memorable roles from the '90s: Sebastian Valmont. He's handsome, of course, and funny in a totally twisted, dark sort of way, but not even the occasional cute moment with Annette (Reese Witherspoon) can distract from the fact that he's got his fair share of issues. If you're one of those fans who can't hear "Colorblind" by the Counting Crows without picturing Ryan at the top of an escalator, then relive your complicated feelings toward Sebastian with the emotional ups and downs — in GIF form.

First Impression: He's Undeniably Cute
Columbia Pictures

First Impression: He's Undeniably Cute

But Also . . . a Little "Off"
Columbia Pictures

But Also . . . a Little "Off"

Yes, He Looks Good Shirtless
Columbia Pictures

Yes, He Looks Good Shirtless

But Even the Good Moments Seem Strangely Dark
Columbia Pictures

But Even the Good Moments Seem Strangely Dark

He's Funny in an Outrageous Sort of Way
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He's Funny in an Outrageous Sort of Way

But Wait, Ohmygod, Him and His Stepsister, WTF
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But Wait, Ohmygod, Him and His Stepsister, WTF

But Then He's Just Straight-Up Cruel
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But Then He's Just Straight-Up Cruel

You're Like, "Yes, He's in Love!"
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You're Like, "Yes, He's in Love!"

But Also, He's a Manipulator
Columbia Pictures

But Also, He's a Manipulator

On the One Hand, He Seems to Truly Care
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On the One Hand, He Seems to Truly Care

But He's Also Just a Cocky Jerk
Columbia Pictures

But He's Also Just a Cocky Jerk

Still, the Adorable Moments Tug at Your Heartstrings
Columbia Pictures

Still, the Adorable Moments Tug at Your Heartstrings

And You Actually Cry Whenever You Hear "Colorblind"
Columbia Pictures

And You Actually Cry Whenever You Hear "Colorblind"

Because Even Though Sebastian Is Sort of the Meanest
Columbia Pictures

Because Even Though Sebastian Is Sort of the Meanest

He Also Isn't
Columbia Pictures

He Also Isn't

Yeah, This Moment Pretty Much Sums Him Up
Columbia Pictures

Yeah, This Moment Pretty Much Sums Him Up