Called the "most-sought-after sixteen-year-old since Harry Potter" by TransWorld Skateboarding, Ryan Sheckler has been skating at X Games since he was just 13-years-old, when he became the youngest athlete ever to win gold (Park, 2003) at X Games. Since then he has become one of the core street skaters in the industry, but he has yet to medal in Street at X, something that has a lot to do with his small size. Each year he gets closer though. His arsenal of tricks, clean airs and speed helped him take the season's top honors at the 2005 Dew Tour, and overall points champion of the WCS 2005 World Street season.

At XG 2003, Ryan Sheckler (13 at the time) became the youngest athlete ever to win XG gold, which he did in SKB Park. While Ryan struggled at XG 2004 with the new street format, he still rules at park contests, and won the first Dew Action Sports Tour stop (Louisville, June 2005) which was a similar format to XG 2004. For 15-year old Sheckler, however, it's the change in sponsorship from World Industries to the core company Almost that is transitioning him into a core media skater. His first major video part came out in fall 2004 in the Almost Round 3 video.

In 2003, (at the age of 13 and weighing in at less than a hundred pounds) Ryan became the youngest skateboarder to win gold at XG. He also swept the entire skateboarding comp scene, winning Gravity Games, SCJ, VTC overall, WCS North American Street overall and WCS World Street overall. Since XG '03, he's appeared in Sports Illustrated For Kids, put in an appearance (with Tony Hawk) on Teen Nickelodeon, filmed for his part in the new Almost video and traveled to Spain, Australia, and Canada. In the fall ('04), Ryan will start his freshman year at San Clemente High School.