far as i can tell there are three who are neck and neck:
phelpers - world record for milking it. r.i.p.
tony hawk - the most famous, most respected, most vertiest, he is living the dream and so is his family. still ripping and putting out video games. recognized all over the world.
rodney mullen - won so many contests but was never a top selling pro. went in to manufacturing, changed the game, and made money on nearly every skateboard sold by world industries and co. still ripping and still getting dwindle money. people who don't skate have no idea who he is.
in a sport where most folks get broke off and smoked before they even take a picture, these dudes went the distance for decades