In 1988, he cofounded The State at NYU. In 1995, the sketch-comedy troupe found a home on MTV.
Cocreated Comedy Central's Reno 911! and Viva Variety, as well as MTV's The State with Robert Ben Garant and Kerri Kenney-Silver.
Met frequent collaborator Kerri Kenney-Silver at a summer theater camp when they were 16.
Has cowritten screenplays with Robert Ben Garant for films including Herbie: Fully Loaded (2005), Reno 911!: Miami (2007), Night at the Museum (2006), and Night at the Museum: Battle of the Smithsonian (2009).
Coauthored Writing Movies for Fun and Profit: How We Made a Million Dollars at the Box Office and You Can, Too! (2011) with his writing partner Robert Ben Garant.