Hmm.
Well, I personally find that Amanda Palmer puts out a lot of really emotional stuff, and she might well be right up your alley--though she's very much an acquired taste. (She was also in a band called The Dresden Dolls earlier on; they're just as worth listening to.) I've also been enjoying Ben Folds a fair bit lately, and a lot of his stuff is definitely tearjerker material.
Also, Death Cab For Cutie and The Mountain Goats.
(And, because I love them so much, I'm gonna recommend They Might Be Giants, just because they're that good.)
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"We were once so close to Heaven; Peter came out and gave us medals, declaring us the nicest of the damned."
~They Might Be Giants, "Road Movie To Berlin"