Studied improv under Del Close and Charna Halpern at the I.O. (formerly the ImprovOlympic) in Chicago.
Appeared on Saturday Night Live from 1995 to '96.
In 1998, he began playing Gerald "T-Bones" Tibbons with Dave Allen in The Naked Trucker Show, a music-and-comedy act performed at alternative Los Angeles nightclubs. The Naked Trucker & T-Bones Show, a TV series based on the act, aired on Comedy Central in 2007; and the album The Naked Trucker and T-Bones: Live at the Troubadour was released that same year.
Had his breakout role in Anchorman: The Legend of Ron Burgundy (2004).