Hahaha... I used to listen to this song getting over this guy/'it's complicated' and just cry and sometime sob:
[YOUTUBE="http://www.youtube.com/watch?v=mOBwWnoNI6U"]Rachael Yamagata - Elephants[/YOUTUBE]
Watch out. The lyrics are kinda depressing, but really beautiful. Lots of other good sad ones on that album too. The strings at ~2:35 would always KILL me, and then the percussion at like 3:00, and the last line 'keep one eye open at night'. Also
this song, also I would cry, also the same guy. Ohhh gromit.

And this one is weird because sometimes I feel like it's a really sad song but sometimes I feel like it's really triumphant, almost.
[YOUTUBE="http://www.youtube.com/watch?v=RVHV2nL5JZ0"]Regina Spektor (again!) - Human of the Year[/YOUTUBE]
Like, when we first found out my uncle had cancer... it seemed like a more sad song to me then. But now, with a little bit of perspective on the situation, it seems to have a different tone.
I feel like I am blabbing...
[YOUTUBE="oAgceen153I"]Blackbird[/YOUTUBE]
Oh, good one.