Life in the Rob and Big household changes dramatically when the guys discover that their bulldog, Meaty, needs a little buddy. After a little research, Rob finds the perfect companion for his favorite puppy: a Mini-Horse. Owning miniature livestock turns out to be a little more than the guys bargained for, and drastic measures become necessary to accommodate the tiny horse.

An airbrushed van leads Rob and Big Black on a quest to travel through time with Rob's "Hyper-Dimensional Resonator." Big Black is skeptical, but Rob convinces him to travel to Montreal to visit a "time travel expert" named Dr. Z. When they return to LA, Big Black surprises Rob with his own, throwback version of Time Travel.

Rob is thrown deep into the "Dirty South" when Big Black invites him to Sylvarena, Mississippi, for the Boykin family reunion. The boys overdose on southern cooking, southern living, and Big Black's crazy Uncle Jerry.

Rob and Big Black call out Drama, Rob's cousin, for being a lazy assistant and decide to put him on "waivers" until he shapes up. When Drama is seemingly unfazed by the threat, Rob threatens Drama by interviewing a professional executive assistant as a potential replacement. On top of that, the guys struggle with an "aggressive mini horse." In the end, Rob and Big Black figure out a way to remind both Drama and Mini Horse how good they all have it in the Hollywood Hills.

Big Black reveals to Rob that he used to be a male stripper with the stage name "Black Lavender" for a brief time back when he had a full head of hair. The two decide it's time to resurrect Black Lavender for one last show at a Hollywood strip club, but not before they find him a brand new head of hair.

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 reinvents himself as Bobby Light, a self-proclaimed "one hit wonder, R&B sensation." With the help of his cousin, Drama, and The Chunky Boys (Big Black and Bam Bam), Rob hops into the makeshift recording studio in Big Black's closet and records a song called "Dirty Girl." Rob and Big Black decide to shoot a low-budget music video for their hot new song, but realize the video will not be complete until they fly Big Black's Uncle Jerry out to LA to take a starring role.

In the season two finale, Rob and Big Black both add a new car to their growing collection of vehicles. In order to make room for the new rides, Rob plans to give away his old truck (the UAV) to the first skater that can beat him in a game of "S-K-8" and beat Big Black in a game of Roshambo (Rock, Paper Scissors). Later, Rob is both shocked and bemused to find himself dubbed a "C-Lister" on the cover of the Wall Street Journal.