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Ballad of Hollis Brown by Bob Dylan is definitely the saddest song I've ever heard. It's not sappy and whiny though, it's sadness comes from smart use of lyrics, and really, the fact that it's sung in the second person. It involves the listener much more than other "sad" songs.
Don't have a link since Youtube sucks.
Another worth mentioning is Romance In Durango by Dylan. Fantastic song, not only one of the saddest songs I've heard, but it's also one of my favorites.
Tons of great, sad songs here. Elliott Smith, The Cure, Joni, Johnny Cash, Radiohead. Can't go wrong with those.
But I have to go with Tom Waits-Ruby's Arms. Just because it's so simple, and ordinary, a narrative of a man on his way out the door, leaving for the last time.
Tom has been more clever, more bombastic, more descriptive, a better storyteller in other songs. But this is the one that gets me.