Ryan Phillippe Photos

Juliette Lewis and Ryan Phillippe showed their off-screen chemistry while discussing their new ABC show Secrets & Lies at the TCAs in LA on Wednesday.
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Juliette Lewis and Ryan Phillippe showed their off-screen chemistry while discussing their new ABC show Secrets & Lies at the TCAs in LA on Wednesday.

Ryan Phillippe
Ryan Phillippe
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Source: FameFlynet
Ryan Phillippe's Surprisingly Fit Physique
Ryan Phillippe's Surprisingly Fit Physique
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Ryan Phillippe may have turned 40 this year, but he still had the looks of a 20-something during his trip to Miami in June.

Source: FameFlynet
Ryan Phillippe carried his backpack in NYC on Monday.
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Ryan Phillippe carried his backpack in NYC on Monday.

Ryan Phillippe Photos
But Also, He's a Manipulator
But Also, He's a Manipulator
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On the One Hand, He Seems to Truly Care
On the One Hand, He Seems to Truly Care
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He Also Isn't
He Also Isn't
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You Spot a Glimmer of Genuine Human Emotion
You Spot a Glimmer of Genuine Human Emotion
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But Even the Good Moments Seem Strangely Dark
But Even the Good Moments Seem Strangely Dark
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He's Funny in an Outrageous Sort of Way
He's Funny in an Outrageous Sort of Way
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First Impression: He's Undeniably Cute
First Impression: He's Undeniably Cute
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And You Actually Cry Whenever You Hear "Colorblind"
And You Actually Cry Whenever You Hear "Colorblind"
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But Also . . . a Little "Off"
But Also . . . a Little "Off"
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Yes, He Looks Good Shirtless
Yes, He Looks Good Shirtless
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But He's Also Just a Cocky Jerk
But He's Also Just a Cocky Jerk
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But Then He's Just Straight-Up Cruel
But Then He's Just Straight-Up Cruel
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Because Even Though Sebastian Is Sort of the Meanest
Because Even Though Sebastian Is Sort of the Meanest
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You Pretty Much Melt Over That Smile
You Pretty Much Melt Over That Smile
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You're Like, "Yes, He's in Love!"
You're Like, "Yes, He's in Love!"
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Still, the Adorable Moments Tug at Your Heartstrings
Still, the Adorable Moments Tug at Your Heartstrings
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Yeah, This Moment Pretty Much Sums Him Up
Yeah, This Moment Pretty Much Sums Him Up
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But Wait, Ohmygod, Him and His Stepsister, WTF
But Wait, Ohmygod, Him and His Stepsister, WTF
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You Aren't the Only One With a Complicated Crush on Sebastian Valmont
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. This week Phillippe turns 40, so to celebrate his milestone birthday, we're taking a look back at one of his 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.

. . . Ryan Phillippe!
. . . Ryan Phillippe!
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The Twilight costars were both linked to Reese Witherspoon's ex-husband, Nikki in 2007 and Ashley in 2013.

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