- Considered working as a sportscaster as a back-up plan to comedy.
- Performed in two sketch-comedy troupes during college, Just Kidding and Comedy Company.
- Was a member of the Second City comedy troupe during the mid-1990s.
- Appeared in the Second City's stage production of Piñata Full of Bees in 1995 and 1996.
- Wrote for Late Night With Conan O'Brien for 5 years, during which time the writing staff was nominated for 5 Emmy Awards.
- Appeared in Superchunk's music video for the single "Void" alongside longtime collaborator Jon Benjamin.
- In 2015, was named 31st on Time Out magazine's list of 50 Funniest New Yorkers.
- Is a member of the comedy band Detroit Octane.