Song: "Jump" by Kris Kross
Level Of Embarrassment: Meh

Timberlake has a lot of street cred, which was not something that looked likely when he was the ramen-headed boy in N*SYNC. He built up his reputation, earned his platinum records, and now gets to sing alongside greats like Jay-Z. That's why you have to respect the man for risking it all by rapping along to Kris Kross' "Jump" in the rom-com, Friends With Benefits. It's not pretty—he's in a robe, jumps enthusiastically along, and admits to dressing like the duo, who wore their clothes backwards, for three Halloweens in a row. But Timberlake is an unstoppable force. We're pretty sure at this point in his career he could actually bring back the backwards clothes and people would jump on that shit like it's a suit and tie. —TA