Cry Me A River
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Of course, rumors abound that Timberlake and his co-star Mila Kunis are dating, but you really never know with JT.
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.
Timberlake spices up Jimmy’s show with his ridiculous rapping (which is actually not bad) and self-mocking dance moves.