He was an American icon. He just one aspect of the human existence and a huge part of Americana.
Here, he pairs with another talented musician.... who wrote and played in this song:
Many times he looked troubled, many times he looked a bit sad. I think it stopped just short of what I would say, "tortured"..... but he looked like he never really forgave himself for his shortcomings and mistakes.
He really took it hard when the love of his life died and that's when he gave up. He quit. He quit taking his medication and allowed himself to die earlier than he should have, because he was so grief stricken.
One of his latest works was a remake of a Nine Inch Nails song called "Hurt". It was so dark and so sad that I won't post or link to it, you can look it up for yourself on You Tube if you are so inclined.
Musically, he was the kind of artist who could take any song by almost any other artist, and make it his own.... in his own special way. This one you will recognize from U2: