The Naked Cowboy is a guy who walks around Times Square in nothing but a pair of white briefs with a guitar, a cowboy hat, cowboy boots, and really long nasty looking hair. People put money in his boots and take pictures with him and stuff.
As for the Hot or Not part of it: Not. I found him interesting many moons ago, but now it's just basically not even something I notice when I'm in there. Its the kind of thing where it was cool before he became someone people actually LOOK to see, now it's just kind of like "okay, so what? Hes always there."
And hang on, when did you win the discus?