I should probably think about this for a long time, but some that come to mind immediately are:

"A Fool Like Me" by Bruce Murdoch

"Better Than Me" by Ron Horvarth (Dharmabum)

"Porchlight Blues" by Steve Lee Rich

"The Green Heart of Harlow" by Kevin McGrath

"Old Blue Suit" by Jerry Rasmussen.

Somehow I failed to mention khandu's "Dirt Road Shoes" and any number of beautiful songs by Jed Marum - in particular "The Streets of Falls River"... This is just impossible...