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Beloved Wife by Natalie Merchant ranks pretty high on my list of sad songs. So does "Me and a Gun" by Tori Amos.
Speaking of N Merchant - whatever happened to her? River from Tigerlilly gets a vote as well.
"I Wish My Baby Was Born" by The Be Good TanyasDo yourself a favor and don't listen to this track or anything from Chinatown. I'm fixin' to cry right now just thinking about it.