39. Shannon Sharpe
Cockiest Quote: “People say, 'Since you got rich and famous, you've become insufferable.' I say, 'That's not true. I've always been insufferable.”'
He may be rocking an '80s part in his hair in 2012, but the Super Bowl-winning, HOF tight end for the Broncos and Ravens thinks the world of himself. He's one of the best tight ends to ever play the game, but we'd be hard pressed to find another guy with his combo of a great gift of gab and confidence to boot. He currently serves the “Charles Barkley” role for CBS's football show but over the years he's given us some gems like the meltdown of the year and the Ray Buchanan war of words. Yo Ray “he might got a body” though? #youhadnochance