Speaking of Waylon Jennings, Highwayman is also a great song. If my memory hasn't failed me yet, it's Waylon Jennings, Niel Young, Kris Kristofferson, and Willie Nelson. No Cash, but still worth the $$.
Highwayman is a great song, but the Highwaymen was actually an outlaw country supergroup of Willie, Kris, Waylon,
and the Man in Black himself. See, mentioning that song was more relevant to this thread than you knew!
From what I've read, Stan Jones, not Fred Penner, actually wrote
(Ghost) Riders in the Sky . And its been played by tons of artists. Johnny does one of the best versions I've ever heard.
Although, yeah its actually a Kristofferson song, I absolutely love
Sunday Morning Coming Down. From his earlier years, I like
There You Go.
Of course
Daddy Sang Bass is absolutely poignant, and brings back fond memories of singing along with my own dad, also a deep bass. As a kid, Johnny Cash was almost the only non-classical I ever listened to with my parents. And for yet another song that has already been mentioned, his duet with Dylan on
Girl From the North Country is heartbreaking. And for special topical relevance with the Clint Eastwood movie and all,
The Ballad of Ira Hayes is really wonderfully angry.