Part 1: "Waymore's Blues" from Dreaming My Dreams (1975), Waylon Jennings
Part 2: "I've Been All Around This World" from Reckoning (1981), Grateful Dead
(Yes, that is a Wharf Rat tease...and yes, that is a Cinnamon Girl outro)
I used to hate that the D string went out of tune by the end of this one, then I realized that I kind of liked it...fits the spirit of the medley and the theme of the song...kind of...oh well :-)
"The D string, string of continuity...we're not going to worry about continuity, we're not going to worry about the D string." Col. Bruce Hamptom, Ret, teaching guitar.  Outside Out (directed, written by M. Gordon).