40. Ryan Sheckler
Hateful lowlight: His entire reality TV show run, but mainly the multiple points when he cried on camera.
The Justin Bieber of the skate world, ESPN's Allison Glock summed up Ryan Sheckler pretty well in 2008: "Sheckler is a hot guy who happens to skate." He's a talented skater who has jumped at the chance to sell-out and capitalize on his looks, as evidenced by his teenybopper following and the two seasons of his MTV reality show, Life of Ryan, which focused more on his shirtless physique and girlfriend problems than his actual skating.