In 2003, he was hired as a sketch writer for "Saturday Night Live" and became a cast member from 2005 to 2013. He has appeared on television in "30 Rock", "The Cleveland Show", "Eastbound & Down", and other shows. In 2009 he was part of the legendary and last episode of "Joe Buck Live" when Artie Lange ,high on Vicodin and whisky, called Jason a " Lucky Pierre" and verbally fought with Joe Buck live on air. This resulted in the cancellation of "Joe Buck Live". He played "Schmitty" on "It's Always Sunny in Philadelphia". He is also known for his roles in the movies "Hall Pass", "Horrible Bosses", "Epic" and "We're the Millers".