- 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).