When in a particularly maudlin mood,Lou Reed's "Berlin" album has a pretty heavy overall effect
Also..I made a cd compilation last Winter that ended with Camper Van Beethoven's "Come On Darkness" followed by Bonnie Prince Billy's "I See A Darkness" and Johnny Cash's version of NIN's "Hurt"..didn't bring me to tears so much as make me feel as if someone had excavated my chest.
I've actually been thinking of doing a "Sad" comp for awhile and ending it with those songs..just have to fill in the rest,so I'll be watching this thread for ideas
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