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Originally Posted by Jetstream
The Lonely Shepherd by Zamfir has nothing but heart-wrenching acoustics and melodies.
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Heart-wrenching yes, but I find that song rather inspirational and soothing... definitely not what I'd call depressing.
Anyway, Dashboard Confessional and Howie Day definitely have some good and depressing songs... and I agree with those who mentioned Hallelujah by Jeff Buckley.