Neil Young - Tonight's The Night
Lisa Germano - Geek The Girl
Joni Mitchell - Blue
Nico - The Marble Index
Nick Drake - Pink Moon
Leonard Cohen - Songs Of....
Townes Van Zandt - Our Mother The Mountain
Daniel Johnston - 1990
Jackson Browne - Late For The Sky
Gram Parsons - Grievous Angel
John Prine - John Prine
Joy Division - Closer
Eels - Electro-Shock Blues
Julia Holter - Tragedy
I've only cried a couple handfuls of times from age 8 to 22, but within the past year I've cried more than double that. Here are some albums with a few songs that have made me cry, though I wouldn't consider most of these all-around sad albums (I don't know if many albums can be totally depressing).
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And then here's some albums have a few songs that get me in the mood to cry, but can't quite get me there yet.
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