Just about the saddest song I ever heard was sung by Ethel Waters, probably in the 1930's. I can't recall the title, but it's a mother singing to her children telling them that daddy isn't coming home tonight. (He's been lynched.)
If anyone knows the title, please post it.
In a similar vein is "Strange Fruit," sung, I think, by Billie Holiday. It's also about lynchings.
Songs that make me choke up include: The Sweetest Gift (sung by The Judds) Mr Tanner (Harry Chapin) Where've You Been? (Sung by Kathy Mattea) Un Cananien Errant My Yiddishe Mame
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