Drive-By Truckers: Outfit
One of the best advice songs ever is Outfit by The Drive-By Truckers. I'll default to the songs author, Jason Isbell, to tell you the meaning:
Jason: "This one focuses on the advice I got growing up, mostly from my father. We recorded the song just before Father's Day and I gave Dad a copy as a present. I'm really fond of Cooley's psycho solo and Patterson's guitar harmonies toward the end."
This song was one of the standout tracks on their 2003 New West Records debut, Decoration Day and personally, I don't think any advise theme is complete without this one in it.
Submitted by Autopsy IV