Going to throw TvZ into the mix. Guy was a wondering folk-poet who penned some of the most tragic and heartbreaking music ever written or recorded, not to mention wrote a few hits for the likes of Willie, Haggard, and Parton. Man lived an incredible, tragic, short life.
Townes Van Zandt songs to check out:
Waitin' Around to Die (Heartworn Highways performance is very moving)
Pancho & Lefty
To Live is to Fly
Rake
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