Tom Rush, Four Bitchin' Babes, Christine Lavin, Arlo Guthrie, Red Clay Ramblers ... these should get me back on track with current artists who frequently use humor. More regionally located (but with available albums) to Southern Chesapeake, Them Eastport Oyster Boys are great, too.

For political satire, The Capitol Steps are good. Garrison Keillor also uses a lot of humorous songs, but I'm not sure if he goes with the spirit of this thread.

Definitely going to look up some of the above.