
One of the most underrated songwriters of all time (imho), Mike Cooley is best known - if known at all - for his work with the Drive-By Truckers. He has written some of the best songs never recorded by the Rolling Stones and Johnny Cash (which will hopefully give you some kind of bearings for what to expect if you are stumbling upon him for the first time). Unlike Patterson Hood of the DBTs, who has any number of solo shows available for your delectation on the awesome archive.org, Cooley's solo shows are rare as rocking horse shit.
If you check in the comments you'll find links to every one he's ever done (afaik).
Cooley makes me laugh, Cooley makes me cry. And he will kick your ass too, musically speaking (and maybe even otherwise if you rile him).