In 2008, he transitioned into comedy, directing the films Pineapple Express and Your Highness, as well as episodes of the HBO comedy Eastbound & Down. In 2013, he returned to his more dramatic roots with the independent film Prince Avalanche. Since then, he has worked between the two genres, directing the films Joe, Manglehorn and Our Brand Is Crisis, and episodes of the television comedy-drama Red Oaks, which he also executive produces.