Justin TimberlakeJustin Timberlake is no stranger to winning awards, though the one he was given on Friday night was certainly a bit stranger than usual. Wearing a bra, wig and high heels, the six-time Grammy and two-time Emmy-winning singer, producer and actor was presented with Harvard University's Hasty Pudding Theatricals "Pudding Pot" and named its 44th Man of the Year.

Half an hour earlier, Timberlake, smartly dressed in his Sinatra-styled gray suit and gray fedora, tie (also gray) and white shirt, arrived at Harvard's small New College Theatre for the traditional roast, based around that old Ivy League predilection for drag and bawdy humor. The vaudevillian 'This Is Your Life' skit soon had him wearing a curly blond wig, like the cherubic singer's hair when he first found overnight fame in 'N Sync.