In "Escape to Beer Mountain: A Rope of Sand", he busted JFK's party for underage drinking. He was about to arrest Gandhi and Joan of Arc, but then Abe stopped him, admitting that the beer he bought was non-alcoholic. The Sheriff mocked him for being so uncool, getting Abe laughed at by everyone at the party.
In "Sleep of Faith: La Ru D'Awakening", he was the police man featured in Doug Prepcourse's flashback. The sheriff fell asleep, while driving one night and Doug, who was in the truck next to his police car, tried giving him a little car nudge to wake him up. However, he hit the car too hard, sending him off of a cliff, and crippling him with the crash.
In "Litter Kills: Litterally", he managed a bunch of Prisoners, during their trash cleaning community services. When Gandhi got mixed in with the group, while wearing his orange jumpsuit, he was mistaken for a prisoner and got taken to jail. The sheriff fell asleep, allowing for Gandhi to swipe his keys and bust everyone out.