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Friends With Benefits (2011)

Of course, rumors abound that Timberlake and his co-star Mila Kunis are dating, but you really never know with JT.

Bad Teacher (2011)

Timberlake co-stars along with ex-girlfriend Cameron Diaz and bromance superman Jason Segel. JT plays a hot rich guy, which was a real stretch for viewers, but he somehow made it believable.

Late Night with Jimmy Fallon (2010)

Timberlake spices up Jimmy’s show with his ridiculous rapping (which is actually not bad) and self-mocking dance moves.

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