Caldwell appeared in three episodes of Hannah Montana in 2007 as Thor, a new kid from Minnesota whom Jackson befriends, and later that year played the bully, Bubba Bixby, in the Nickelodeon movie Shredderman Rules, as well as a small role in Michael Bay's Transformers. In 2008, he had a role in the film Drillbit Taylor and a lead role in the comedy film College alongside Drake Bell.