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I definitely agree with a bunch of these. I've got quite a collection of depressing songs, but here are some of my favorites that might not have been mentioned:
The Point of It All-Amanda Palmer
Skinny Love-Bon Iver
We Are Nowhere and It's Now-Bright Eyes
Delicate-Damien Rice
King's Crossing-Elliott Smith (or any of his songs, really)
Doll Parts-Hole
Where Have You Been?-Manchester Orchestra
Broadripple is Burning-Margot & the Nuclear So-and-So's
Everything Was Beautiful and Nothing Hurt-Mewithoutyou
Sorrow-The National
Note to Self:-Owen
This Place is a Prison-The Postal Service
A Better Son/Daughter-Rilo Kiley
The Weary Kind-Ryan Bingham
World Spins Madly On-The Weepies
Hope this helps.
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