Wish I gotten some of Rockyboy's 2007 action on the impending demise of Wilco!
Saw Uncle Tupelo a few times in the early 90s -- in 1990, in the nearly empty Blind Pig in Ann Arbor, which was a revelation. A truly remarkable band. I enjoyed the first Son Volt and Wilco releases (the material on both rather like their Uncle), but less so the later stuff.
I second Streetdaddy on Whiskeytown.
Others to look for in the UT genre are the (sadly defunct) Nadine (esp. "Downtown Saturday"), Slobberbone, and Two Cow Garage (The latter two often give s**t kicking shows).
Off to listen to Fleetwood Mac with Rockyboy!
John