Mentioned already:
Wreck of the Edmund Fitzgerald - Gordon Lightfoot
Hurt - Johnny Cash
A few classic country choices:
Old Violin - Johnny Paycheck
Long Black Veil - Lefty Frizzell
Old Rivers - Walter Brennan
In My Next Life - Merle Haggard
The Last Thing I Needed First Thing This Morning - Willie Nelson
I'm A Long Way From Home - Waylon Jennings
He Was a Friend of Mine - Jerry Jeff Walker
And probably the most famous sad country song......
He Stopped Loving Her Today - George Jones
(Oops... I saw i was beat to the punch a few posts ago)
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