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This one probably doesn't count... Kristofferson sort of danced around country & western conventions. Couldn't find a good copy of Duvalier's Dream, so here's Casey's Last Ride... Darby's Castle's a fave, too:
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The real tragedy of this one is that country's audience, since it skews right, has largely abandoned the concerns outlined here. A lesson that patriotism and love of country, in part, also means environmental stewardship seems to have been lost on an entire half of our population in the years since then. Not only lost, even, but fought indignantly, by reflex, as if consumption and waste were American duties written into the Constitution:
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Can't get much more "classic" (or dark) than an old Scottish murder ballad -- a form often adapted by early country music -- and sung by Ralph Stanley... (Though "The High Strange Drifters" still do my favorite version)
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The song itself is old enough to be "classic"... It's been covered by even greats like Bob Dylan and Joan Baez, but this "Crooked Still" does my favorite version:
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Another strangely upbeat piece about a grisly beating and murder:
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Johnny at the end of his life, singing the classic "Ain't No Grave":
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