I think this one's surreal: a guy from Charleston SC (who won "Worst Call 2008" at the Best Show Awards Show) calls in on the topic "I love ya, but..." and is such a downer that Tom mocks his mopey voice for the next 45 minutes while taking calls. "Who should go shoppin' for a coffin?"
March 25, 2008: Talk Of A Bunch Of Different 'Funny' Things, Probing Discussion Arises From The Topic, Which Is 'I Love Ya, But -'. Then Tom Gets Jamesed. Then The Debut Of 'Coffin Talk'.
I don't know if this meets your criteria in terms of sound environment.
PS there's this-
July 20, 2004: Tom Does A One Man Version Of The Entire Movie Road House! Also, An Unfair Record Review Of The New Wilco Album.