8 Milestones in the Evolution of Justin Timberlake

5. SNL and "Dick in a Box"

Grammys became de rigueur for Timberlake as a musician, but who could've guessed that he'd end up a shoo-in for Emmys as well? As the most celebrated Saturday Night Live host of the past five years, he gave the series' Digital Shorts a major boost when he co-starred with Andy Samberg in the viral sensation "Dick in a Box" (also co-starring a hilariously thunderstruck Maya Rudolph). Yes, he'd make a cameo in "Jizz in My Pants" and come back to reprise his "Dick" role in "Motherlover," but Timberlake's first SNL stint remains most iconic.

6. The Social Network

Whoever cast Justin Timberlake as washed-up Napster entrepreneur Sean Parker in The Social Network deserves a special backrub, because the cocky role riffed on Timberlake's casual (but likable!) arrogance and 1999 musical credibility. He even unleashed the film's signature line: "A million dollars isn't cool, you know what's cool? A billion dollars." Almost everyone in Aaron Sorkin's 2010 Oscar-winning masterwork catapulted to bigger things afterward -- even one-scene wonder Rooney Mara has her own mega franchise -- but The Social Network transformed Timberlake into bona fide megaplex bait.

7. Bad Teacher

Did you see Bad Teacher? You didn't love it, which is a shame. But you consciously noted the fine casting of Timberlake as a pretty faculty member who plays a realistic romantic foil to Cameron Diaz's titular matriculator. Bad Teacher was more a solidification of Timberlake's talents than a bold step forward, but solidification is all you need to ensure continued opportunities on the big screen.

8. Friends with Benefits

It seems like we've heard about Friends with Benefits for about eight months now (oh, wait -- we have!), but the new news on the sexy romp is this: Timberlake plays an editor at GQ named Dylan (groan) who forges an emotion-free, sex-based relationship with his friend Jamie (Mila Kunis). No Strings Attached is a better version of this idea, but Timberlake may have a new career ahead of him as a shirtless... something. Shirtless something. Timberlake will next be seen in In Time, a sci-fi actioner with Amanda Seyfried out later this fall.

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