Dar Robinson, the greatest of all stuntmen. This man's confidence was unthinkable (narrated by Chuck Norris!):
<a class="postlink" href="http://en.wikipedia.org/wiki/%C3%96tzi_the_Iceman" onclick="window.open(this.href);return false;">http://en.wikipedia.org/wiki/%C3%96tzi_the_Iceman</a>
I saw a really good parkour guy running from the cops once. He was really spectacular - until the fat, lumbering cop made a beautiful throw across about 30 feet I guess, with his nightstick, wrapped (and broke) his ankles mid jump - you could hear the bone break from a good 30 meters away. Mr Parkour went teeth first into a concrete step. He was spitting bloody chunks of his teeth out when the cops eventually lumbered over to him and pepper sprayed him for making them fucking run. Then they cuffed him to the stair rail while they waited for the ambulance to come and take him to get his burning eyes, broken ankle and shattered teeth seen too. I really like watching parkour - but running from cops is a stupid idea.
Richard Branson Everyone mentioned here is cool, but Richard Branson actively develops new ways to be totally rad. I mean, he's investing in space tourism, he does his own stunts and there is absolutely no sane reason for those stunts, c'mon. And then there's this: NSFW Kite surfing (cool) off his private island (cool) with a naked model (cool) on his back. It's cool fusion, the whole is greater than the sum of its parts. All these people, they're cool when they're doing their thing, but at the end of the world, all that will be left will be the cockroaches, and Richard Branson making the cockroaches feel like failures.
Can I nominate Jimmy? I don't really care for his music, but the dude has lived quite a life. Ever seen how much shit this guy owns the rights to?