This started as a thread in the cyclingnews.com Forums...my answers are below.
Ballsiest = Lance (given that he has only 1 ball) - NOT! Actually, all pro's are ballsy, b/c cycling is the hardest sport in the world - either that, or "cycling is for pansies."
Bravest = Tie between Cancellara (for his stage 7 TdF descent while in Yellow to regain leaders) and DiLuca (for riding to 2nd in the Giro whilst doped on CERA)
Craftiest = Michele Scarponi (for his 2 Giro stage wins and zero positive tests)
Crankiest = Lance (for his shunning of media in Giro and his hating on Contador all year long)
Creepiest = Jock Boyer (gross)
Fiercest = Thor (SMASH!)
Funniest = Harm Jansen (retired or not, still the funniest)
Likable-est = Mike Friedman (how can you not like a guy w/ the nic' "MeatBall"?)
Loneliest = Danilo DiLuca (for how quickly his team decided to sue him after having been caught doing what they most likely condoned...[see above link])
Scariest = Denis "Crash" Menchov (pity he who follows the Russian's wheel on a day like that of the 17th stage of the 2009 TdF)
Sexiest = Rochelle Gilmore (duh!) [I don't understand why ever dude who answered this question listed another dude, as opposed to a female pro cyclist...]
Shyest = Riccardo Ricco (fleeing the doping control chaperons is evidence of S.A.D., right?)
Toughest = Vino-4EVER!
Virile-est = WTF? Can this really be a category?