Ryan Sheckler has been one of the most identifiable skateboarders since breaking out onto the scene six years ago when, at 14 years old, he won gold at the X Games and first place at the Gravity Games, Vans Triple Crown and Slam City Jam. Sheckler, the three-time Dew Cup champion, also won the skate park finals at the 2009 Dew Tour in Boston (with back-to-back frontside lips, boardslides and 5-0s), placed 5th in the 2009 Maloof Money Cup, and won another two gold medals at X Games 14 and 16 in Skateboard Street. Sheckler has starred in four Tony Hawk video games, five movies, and one reality series (Life of Ryan, MTV).