Justin Timberlake Wigs Out at Harvard's Hasty Pudding Awards

Man of the Year at the Ivy-League college, Timberlake pokes fun at himself alongside drama students in drag

Justin Timberlake's luscious locks have come a long way since the days of N'Sync, but Friday night Harvard's Hasty Pudding Theatricals brought sexy back in a big way—that is, if you were a fan of the prepubescent megastar.

Donning a bleached blonde and tightly permed wig, Timberlake took home Hasty's Man of the Year title, which included a silver Pudding Pot and lots of low blows throughout their signature honoree roast.

"This year's Man Of The Year is a triple threat," they teased, as Timberlake laughed alongside on-again girlfriend, Jessica Biel. "He sings, he dances and he goes straight to DVD."

And that was just the beginning.

The Pudding folks brought Timberlake's past to life, with various versions of Britney Spears, Madonna, and former boyband mate, Chris Kirkpatrick, gracing the stage.

JT's snarky response to seeing a fat-suited, pigtail-wearing, ice cream-inhaling faux-Spears? "That's unfortunate."

By the end of his roast, The Social Network star was dressed in drag with pink high heels and a bra with two gift boxes attached to each cup. (We'll let you draw your own conclusions as to which Saturday Night Live-based joke accompanied that prop.)

"Funny enough, every time I've hosted SNL I've ended up in drag at least once," the good sport said of his getup during his toast. "I love stuff like this."