I've heard a lot of sad songs.
"Something I Can Never Have," by Nine Inch Nails, was the theme song for my quest to be normal and fit in as a young adult. Pretty damn sad.
"Could've Been," by Tiffany, and "If You Don't Know Me By Now," by some forgotten artist, were notable "schmultzy love songs" that I couldn't blame my dad for refusing to listen to back in the '80s.
I'd have to split the prize, though, between Kris Kristofferson's rendition of "For The Good Times," George Jones's rendition of "Our Bed of Roses," and this Christmas song I heard once only, where Mary, as a new mother, is watching over Jesus asleep in the manger and talking to God, with full and complete knowledge of what his life is going to be (no, it is NOT "Mary Did You Know?"). My son was an infant at that time; I already had suspicious about his neurotype and I actually had to pull the car over, curl up on the seat, and sob hysterically for half an hour.
http://www.youtube.com/watch?v=Ovb_iRWcqsc
http://www.youtube.com/watch?v=5cV8e-0V1OY
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"Alas, our dried voices when we whisper together are quiet and meaningless, as wind in dry grass, or rats' feet over broken glass in our dry cellar." --TS Eliot, "The Hollow Men"