probably 'A Long December' by Counting Crows for me.
Damien Jurado has a whole swack of sad songs. 'Denton TX' always breaks my heart.
Sigur Ros' 'Untitled #1' gets me going too, though I'm not sure why as there's no lyrics.
(aside: what do you think of 'April' J Pold? I have it on repeat these days... love it. And that 'Lost Verses' opening track is a sad one).
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The great CP is in dire need of prunes! 
"That's because the productive part of society is adverse to giving up all their wealth so you libs can conduct your social experiments. Experience tells us your a bunch of snake oil salesman...Sucks to be you." ~Calgaryborn 12/06/09 keeping it really stupid!
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