Easily the saddest song I've heard is I want you to live by George Canyon. I didn't read every post in the thread so I'm not sure if it's been mentioned or not but its about a woman whos husband dies and how she copes or doesn't, I suppose, with his death.
Also The Dream, by Carrie Underwood. About a girl whos fiance dies overseas and is about her on her way to her wedding which suddenly turns into his funeral.
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