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The *most* depressing song? Hmmm good question...
I know most of you may not be into country music, but I would have to say the most depressing thing I have ever heard was:
Little Jimmy Dickens - "Raggedy Ann"
It's a song in which a man is talking to an old Raggedy Ann doll as he walks up the hill to his childs grave. Raggedy Ann was the childs doll. As he talks to the doll, he explains the death of the child and his wife, and keeps apologizing that this will be the last time he talks to the doll, for he is about to go off and die himself. It's more a form of emotional torture than a song. So, for me it takes the cake.
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