- Performed comedy with Andy Dick while at Columbia College.
- Wrote and submitted a spec script for The Simpsons and received a rejection letter, which he kept and framed.
- Made his network debut in 1992 on the Fox comedy The Ben Stiller Show; he later became a writer for the show.
- In 1995 joined the writing staff of the HBO series Mr. Show With Bob and David.
- Made big-screen debut in the 1996 romantic comedy Breathing Room.
- Created the adult animated program Moral Orel in 2005.
- In 2009, became a recurring cast member on the NBC sitcom Community. In the second season, cowrote the holiday episode "Abed's Uncontrollable Christmas," which was presented in stop-motion animation.
- Was inducted into his high school's Alumni Hall of Fame in 2011.