Tom Russell is one of my all time favourite songwriters. He's one of the reasons why country music is still relevant today. Well, at least some of it is, though it's not often called country anymore. Most of the good stuff is being packaged as americana or alternative country just to differentiate it from the watered down, paint by numbers stuff that comes out of the corporate bowels.
I always figure the people who claim to like "any kind of music except country" have just never had a chance to listen to real country music. You peel away all the corporate gloss, jettison the repackaged pop tarts, ditch the stereotypes and then add feeling, musicianship and intelligence and you wind up with music that is relevant, powerful and original.
The first one is more traditional, storytelling fare. It's also a great tune. Apparently, Johnny Cash did record this once but it was never released, which is a shame.
His later stuff has gotten more introspective. He's still a storyteller, but the focus has shifted and narrowed.