After five years away from professional skate competitions, Rob decides to enter the world famous Tampa Pro contest in Tampa, Florida. Rob and Big Black hit gator country with pals, Steve Berra and Bam Bam, and before the contest begins, the foursome head out to Tampa Bay for a little high-flying water adventure. Rob and Berra shake on a $5,000 side bet to see who places higher in the Tampa Pro, and Rob threatens to "make it rain" with Berra's money, if he wins.

• Rob Dyrdek
• Jeff Tremaine
• Christopher Boykin

• Dick Van Patten
• Rob Dyrdek
• Christopher Boykin