"Lincoln Park Pirates" by Steve Goodman. Funny drinking song
"Long Black Veil" by the Chieftains with Mick Jagger. You can feel the chill.
"Pancho and Lefty" by Willie Nelson and Merle Haggard. Check out the YouTube video with a cameo of Townes Van Zandt.
"Down Into Mexico" by Delbert McClinton with a special nod for the set-up/follow-up song "One of the Fortunate Few". Ah hell, pretty much his entire catalog is outlaw or pretty close to it.