>> what I’d expect from a third-rate entertainer and very poor guitarist <<
I can’t comment on Willie Nelson’s guitar playing. Never paid it any attention.
But gotta disagree with your calling him a “third-rate entertainer.” I’d say “extremely inconsistent entertainer” would be more accurate.
Of course, many of his performances have been dreadful, especially during the last 25 years. But earlier, his singing could be magnificent.
My favorites are his performances in the Western Swing genre, for example, his renditions of “San Antonio Rose” and “My Window Faces the South.” His phrasing, elocution and pitch on those recordings rank with the great jazz singers, almost as good — dare I say — as Sinatra.
Moreover, he ranks among the giants as a songwriter, maybe the only Nashvillian besides Christofferson who has contributed to the canon of the “Great American Songbook.”
My belief is that if Nelson had never written anything other than “Crazy,” his reputation would be secure. That composition — which some deem the greatest “country” song of all time — has more harmonic complexity than any other C & W hit I can recall. I tried to count the separate chords, but I gave up after ten. That number surely breaks the Nashville record!
(Moreover, “Crazy” even has a key change. Shades of Cole Porter! If you know of another country hit that uses this device, please let me know because I can’t think of any.)
So sure, Willie stinks on many scores — maybe even literally for all I know. But I’ll bet that 50 or 75 years from now, long after his other accomplishments and his misadventures have been forgotten, people will still be humming the melodies of “Hello Walls,” “Night Life,” “How Time Slips Away,” and above all, “Crazy.”
The beat up guitar is part of his schtick. Nothin’ wrong with it. Entertaining is a lot more than singing a pretty tune.
You’re right — some of Willie Nelson’s stuff is surprisingly sophisticated. I even like his lead playing, which someone once described as “earnest” and which I think is the perfect word. Earnest and unpretentious, but he’ll throw in a few harmonically adventurous jazz notes from time to time that let you know he’s not just some rube. I really like Willie’s version of “City of New Orleans”. Such a beautiful song. Listening to it is like watching a movie.