The saddest song ever!

"To Live is To Die" from about 4:30, especially when it hits the clean break.

In metal, it doesn't get much more emotional than this. But the saddest songs ever I could think of are Terry Jacks "Seasons in the Sun" and I've always had a real soft spot for "Cats in the Cradle."

On the really sappy end there's always Meatloaf's "Objects in the Rear View Mirror May Appear Closer Than They Are."
 
Morphogenesis gets me full of emotion every time. heh. the lyrics have more meaning, to me at least. there's more to that album that just quantum physics if you really listen to it. Hiromi's music can be pretty sad, but they sometimes end up resolving to something happy in the end.
 
I have dreams of absolutely breaking down in tears from the beauty of Opeth's "Coil," however really no music has that much of an effect on me in my waking state :( (well, except for soundtracks, cuz of the heavy associations with the story).
 
This.



I went to see the Dresden Dolls live and Amanda came out and played this (and once she started, I knew I was going to end up in tears)...

There are few people who can play this song and evoke that emotion from me, and she did that night... spectacular.

If you're having a hard time picturing it... slow it down about 20 bpm and in free time and sing it with a slightly cracking voice and TONS of emotion... saddest shit EVAR.
 
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damn, its hard to narrow it down to the top 20 saddest songs on my list. love Sting and the Cash track (NIN cover) mentioned above. I thought that Walk the Line should have ended with his version of Hurt. To me, that woulda been the perfect ending to that movie.

anyways, a few off the top of my head:

Black Label Society: Bridge to Cross (esp the guitar solo!)
NIN: The Great Below
Prince: Purple Rain
REM: Country Feedback
Ben Folds Five: Magic
Peter Gabriel: Passion
Toad the Wet Sprocket: Pray Your Gods
Sade: any of a dozen by her, but esp Immigrant and Someone Already Broke my Heart
Joe Satriani: Bamboo
Lisa Gerard: Sacrifice
The Cure: Last Day of Summer

I could go on and on... so many amazingly inspired songs that reach out and just grab you once you venture out of the hard and heavy genres.