- Joined Chicago's acclaimed Second City comedy troupe after graduating from college and remained a member until 1987.
- Met his wife, writer-actor Deb Lacusta, in a Second City improv class; they went on to collaborate on many projects, including their own Chicago radio show.
- Made his big-screen acting debut in the 1986 comedy Nothing in Common, which was followed by a bit part in the 1989 romantic-comedy classic Say Anything...
- Has said the original vocal inspiration for Homer Simpson—back when The Simpsons was an animated short on The Tracey Ullman Show—was actor Walter Matthau; Homer's signature "D'oh!" was adapted from Scottish actor James Finlayson, who appeared in Laurel and Hardy movies.