His third short film, Ice Cream, won the grand prize at the Aspen Shortsfest in 1993.

He directed his first feature, Tomorrow Night, in 1998, which failed to attract any distributors and was later re-released by C.K.

In 2008, he wrote, performed in, directed, executive produced, and edited Chewed Up, and acted in Diminished Capacity, Welcome Home Roscoe Jenkins, and Role Models (all 2008).

has starred in, written, directed, edited, and produced the comedy-drama series Louie on FX.

He played a love interest in Woody Allen's Blue Jasmine and an FBI agent's boss in David O. Russell's American Hustle (2013).

He played the lead voice role in The Secret Life of Pets in the same year.

In the year 2017, the funnyman auteur wrote, directed, produced, edited, and starred in the unreleased seriocomic film I Love You, Daddy.