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unfortunatly i happen to be a connoisseur of depressing songs. The one that gets me right behind the tear ducts the most is Bright Eyes' It's Cool, We Can Still Be Friends. The way he sings the last verse makes him sound like he's drunk with a gun to his head.
The Aimee Mann cover of "One" is pretty poweful as well.
Still Fighting It and Smoke by Ben Folds Five
Most anything by Elliot Smith will make you want to kill yourself. I recommend
2:45 am and Alameda.
" And you say that I hurt you, in a voice like a prayer
Yeah, you say that I've hurt you, and your voice is like a prayer
Yeah, well maybe I hurt you sometimes, but let's contrast and compare
Lift up your shirt, the wound isn't there
I guess that your truth, is just the ghost of your lies
I guess your kind of truth, is just the ghost of your lies
Yeah, your kind of truth, darling, is just the ghost of your lies
I see through them all the time
So I'm pouring some whiskey, I'm gonna get drunk
Yeah, I'm pouring myself some whiskey, I'm going to get really fucking drunk
I'm pouring some whiskey right now, I'm going to get so, so drunk
That I pass out, forget your face, by the time I wake up"
-Bright Eyes, It's Cool, We Can Still Be Friends
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