Most Depressing Songs...

Candle In The Wind, by Kansas.

Edited to add: In the late '50s there was a song titled Endless Sleep, about a girl who drowns and her ghost appears to her boyfriend on beach at night, beckoning him to "come to join me in my endless sleep...." Now that is one downer song.
 
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[video=youtube;dFb1lGMvS3I]http://www.youtube.com/watch?v=dFb1lGMvS3I[/video]

Guy Clark - Desperados Waiting For A Train
 
"Gloomy Sunday" by Rezső Seress

[video=youtube;IN-vbMeJBHA]http://www.youtube.com/watch?v=TiOyvxgcob4[/video]
 
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