How about "Across the Great Divide" by Kate Wolfe
I believe it was written after she found out about her fatal illness (that is what I have heard anyway).
Also I find the song by Vince Gill "Go High on that Mountain" to be sad considering again the context of why he wrote it.
And what about "Me and John and Paul"
And I find "The Day the Music Died" to be so sad in 1959 there was only Buddy for me (Elvis who?)-- that was one of the worst events of my highschool days.
I was a liberal back in the '60's and supported Bobby Kennedy's bid for the nomination(don't ask why)so:
"Abraham, Martin and John" always put a tear in my eye.
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