I happened to talk to the man for about 5 seconds on the phone once and he was very personable. Was sitting at the bar at Browns on a Sunday afternoon back when Kimbrough worked there and I happened to just be sitting next to Nanci Griffith. We were all bullshitting and playing the jukebox and it just came up and Nanci called Mr. Prine to see what he was up to or maybe she knew, I don't remember. Either way, he was on a little tour and was in Ireland at the time and had just got back to, or into his hotel room. He said it was real nice to hear from them and somebody new and that he wished he could be there but he had to take a shower. GMT-6 it could have been either, I guess. Seriously, Nanci handed the phone to me and i just expressed that I was a fan and he said thank you, and that was pretty much it. I don't know any of these people, really- just happened to be sitting there.
The coolest thing, though was that he used to shop at Bi-Rite on Belmont. Saw him there a couple of times and didn't want to bother him, but needed to see what John Prine drove. A big black 90's 4 door Cadillac with gold emblems and the Owner's 3rd generation wreath that you get when Cadillac knows you, also in gold. This was in 2009 or so, and he could have had the newer models I'm sure, but I'm guessing he liked the one he had.