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From:

I'm including lots of alt.country, as that's what I happen to prefer.

Uncle Tupelo and/or Son Volt and/or Wilco. Son Volt's "Trace" is a fantastic album, "Windfall", "Drown" and "Tear-Stained Eye" are favorite tracks.
James McMurtry: I particularly like "Childish Things" and "Restless"; he (and you) might also enjoy "We Can't Make It Here". (@#$%! What with the vet visit on Sunday I forgot about the show at IOTA. Disappointed.)
Steve Earle: something off "The Revolution Starts...Now" perhaps, or if you want to fire up the Wayback Machine, "Copperhead Road".
Rodney Crowell: possibly something from his latest "The Outsider"
Ryan Adams & The Cardinals: something off of "Cold Roses", like "Let It Ride" or "If I Am a Stranger" perhaps. "Jacksonville City Nights" I didn't like nearly as much, but you can stream it from his web site to give it a try.
To go along with that, try some Whiskeytown: "16 Days", "Don't Wanna Know Why" (check out other stuff on "Pneumonia" too)
Lucinda Williams: "Can't Let Go", "Car Wheels on a Gravel Road". I also like "Jackson" a lot. "Passionate Kisses"? "Righteously" is good, but you'll probably want to listen to the whole thing before putting it on a CD for James.
Drive-By Truckers: "Carl Perkins' Cadillac" (Avoid "Tornadoes", as it certainly didn't inspire in me the sort of reaction I think was intended -- I doubt they meant for it to cause hysterical laughter. Oh, it's bad.)

You could also take a quick scan over the X Country playlist from XM for some tracks to check out, and the iTunes Essentials' Alt.Country playlist.