I learned this off a lovely album by a little-known guitarist and singer from Kentucky, Bill Williams, who recorded a couple of LPs for the Blue Goose label in the 1970s. Williams was presented as a blues artist, but his music ranged all over American music, from old rural music to pop songs and ragtime instrumentals.
I heard “I Know What It Means to Be Lonesome” as a rural ragtime song on the borderline between blues and country music, and was not surprised when I later learned that it had been recorded by Lester Flatt & Earl Scruggs and before them by the Carter Family. What did surprise me, when I began researching this post, is that before that it was a Tin Pan Alley pop number, with sheet music published in 1919 and recordings by pop recording stars like Henry Burr on cylinders and discs. The pop song had a verse that the rural artists didn’t sing, and I’m guessing Williams probably got it through the Carters, but the chorus is close enough that there’s no doubt it’s the same song.
I liked this song a lot, and even recorded it on my first album, but had pretty much forgotten about it till I looked at old set lists and noticed how often I played it in the early 1980s. So I worked it up again, adding some faster runs than I could have played back then — my time with Perry Lederman got me interested in the kind of single-string runs Reverend Gary Davis used to play, leading to a brief and unsuccessful attempt to play Doc Watson-style leads with my fingers, which resulted in this kind of picking as a compromise.