Theo Von on the Mike Calta Show Von started his career during his college days on Road Rules: Maximum Velocity Tour. He later reappeared on the Road Rules spin-off, Real World/Road Rules Challenge, competing in Battle of the Seasons, The Gauntlet, Battle of the Sexes 2 and Fresh Meat. Von won The Gauntlet and Battle of the Sexes 2. In 2006, He appeared on season 4 of NBC's Last Comic Standing, winning the title of Last Comic Downloaded. He also used to dig poop holes for a friend.