Missed this one…he passed on Friday.
Nice writeup here:
http://www.popmatters.com/column/180764-in-defense-of-jesse-winchester/
The youtube link from his performance on Elvis Costello’s Spectacle mentioned in the article…
Jesse Winchester - “Sham-A-Ling-Dong-Ding”
RIP 
Loved his self-titled album. Great songwriter, r.i.p.
Never heard of him. Just watched that youtube clip; what a song! It’s late now, but tomorrow I’ve got to do some self-educating.
He did one called “Black Dog” that just gives me chills; very simple lyrically, but it just has this scary quality.
We saw him in concert a few years ago. The venue was a medium-sized church building, and it was a stormy night. The lights went out shortly into the concert. Jesse kept playing and they put candles around, so it was quite an experience - an intimate, candle-lit concert.
I’d never heard of him, either. Thanks for posting the YouTube clip. I like the lyrics and, in particular, the relaxed vibe + picking reminds me of Mississippi John Hurt. Not so much because of the music but the overall soothing quality. Fingerstyle, too.