I was just listening to this, and I think I may have been too reserved in my praise for the Bonnie Beecher tape, i.e. the 5/61 Minnesota Tape. It's great stuff.
I can't find a copy of it to link to, but Dylan's rendition of "James Alley Blues" on here is very affecting. His guitar work - sometime in early 1961 his guitar work really slipped into the pocket, and one of the great joys of his acoustic performances ever after has been the fullness and richness of his guitar playing. Here it's calm and assured, rhythmic but gentle, with a wistful melodic thing that sneaks into it every once in a while.
And the way he delivers the lyrics. No twenty-year-old ought to be able to deliver a line like "times ain't what they used ta be" with this much conviction. And he carries that authority throughout the song: he sells it. This isn't a young man dinking around with a guitar anymore: this is a performing artist performing.
Since I can't link to Dylan's version, here's the original, or at least seminal, version of the song, by Richard "Rabbit" Brown. Notice that in Brown's version, that first line is "Oh, times ain't now nothing like they used to be." A little more ornate, as befits Brown's elegant, tricky vocal line: he was a professional entertainer, and you can hear the professional's slickness in his delivery of the line. I don't mean that as a knock: he's good, and he sings good. We like that.
But Dylan's version simplifies the elocution, and why? I don't know if this was his decision; maybe he learned it that way from someone else. But the effect is to bring a more unadorned feeling to the sentiment, and you can hear how Dylan's vocal capitalizes on that. Rabbit Brown was reaching for professionalism; Dylan in 1961 was grasping for an amateurish, untutored quality that signified authenticity, but which was really another variety of professionalism. You can hear (if you listen to his earlier recordings) how long it took Dylan to get to it.