Bob is pretty much the stereotypical nerd. He, unknowingly, has a rivalry in Litle P, since he "stole" Litle P's coloring book in kindergarten. Squirtle actually stole it. This has lent him to be a running gag, as the main cast usually blames an item's dissapearence on him, even Squirtle.
He is usually only mentioned, having only one appearance. It should be noted that his only appearance is in a dream, and dramatically changed to seen more evil.
In Castle Street: Litle P's Darkest Hour, when Nightmare Mode is played, Billy McBoberson appears as the primary antagonist. He has red wings and horns and attacks by hurling coloring books. It should be noted that this is only a nightmare; the real Billy McBoberson has no idea what happened in the dream.