33. Danny Way
Bonafides From 2002-2012: 5x X Games Medalist (5 Gold, 1 Silver)
In a sport dominated (mostly) by young guys, Way proved his viability well into his 30s, taking home four gold medals at the Summer X Games, and pulling off a series of impressive stunts along the way (jumping the Great Wall of China, setting the land speed record on a skateboard). Oh, and he basically invented a new form of skating with the Mega Ramp. Not bad for an old dude.