Natas
I just spent half an hour watching this four-part biography of Natas Kaupas: part 1, part 2, part 3, part 4.
Natas is fun to watch because he's incredibly creative and he's got this interesting style that mixes the flow of surfing with technical street tricks. (The first two parts cover some of the post-Z-boys era of skating as well.)
And if you like that then Blind's Video Days--featuring a pre-Earl Jason Lee--will be worth your time.

