Just a few more (slightly obscure) choices...
Red House Painters - Drop (the saddest song ever by one of the saddest bands ever... do yourself a favor and track this down...)
Patty Griffin - Be Careful (another amazing artist with tons of sad songs... try "Top Of The World," "Mary," and "Poor Man's House" too...)
Nina Simone - I Love You Porgy (just for the way she sings theopening lines..)
The Cure - Untitled (or just listen to the whole 'Disintegration' album)
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