Bakkedahl's first major television work was on Comedy Central's The Daily Show where he served as a correspondent from 2005 to 2007. After leaving The Daily Show in 2007, he has since moved to Los Angeles and went on to have supporting roles in the films such as Observe and Report, The Heat, and This Is 40. He also appeared in the Snake 'N Bacon animated special on Adult Swim, which aired on May 10, 2009. In early 2010, he co-starred in the comedy pilot Our Show on NBC.