Rob holds a skate contest at the Fantasy Factory with fellow pro skaters Ryan Sheckler, Paul Rodriguez, Eric Koston and others. Prizes include a beaten up dancing gorilla, an early eighties moped, and a 1986 mint-condition Fiero. Rob gets a chance to drag race his newly beefed up 1969 Camaro against Sheckler's new Ferarri, and teases Chanel relentlessly about her alleged crush on Ryan.

In the Season 2 premiere, the world-famous skateboarder dares to purchase and jockey a thoroughbred racehorse. Rob also helps his cousin Drama rise to the status of "mini-mogul" with Drama's burgeoning new T-shirt company.

Rob Dyrdek enters the world of Gymkhana, an artistic genre of precision rally car drifting. With the help of Ken Block, Rob decides to make his own stunt video using his own custom built. miniature rally car.