ESPN X Games Skateboarding lets players experience a simulation of actual skateboarding based on the extreme sporting event, the X Games, that are held annually. The player can choose from eight different real-life skateboarding pros such as Chad Fernandez, Lincoln Ueda, Kerry Getz, Bob Burnquist, Rick McCrank, Colin McKay, Chris Senn, and Carlos DeAndrade and may choose from 64 different authentic licensed skate board designs and equipment.

The main goal of the game is to travel through various locations in three cities, Los Angeles, San Francisco, and New York, competing in a series of events with the main purpose to pull of tricks and stunts with more points being awarded to more complex and trickier stunts. Players may compete in official X-Games locations or choose for more exotic locations like a museum or a cruise ship. It also features music from Linkin Park and Voodoo Glow, among many others.