Saddest songs

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Joined 2008
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Can’t believe it hasn’t been mentioned...

Cowboy Junkies - The Trinity Session

Misguided Angel
I’m so Lonesome I Could Cry
To Love Is To Bury
Walking After Midnight

It’s like the “Swan Song” of sad song albums to me. So sad it makes me feel good. Might have gotten too much attention at one point and become cliche for people, but I still play it several times a year.
 
"Stabat Mater Dolorosa" Josquin Desprez or Orlando diLasso are my favorites. There are over 200 versions.

Steve Vai "Call It Sleep"
YouTube

I believe that it is in the Handel opera "Semele" in which the unfortunate antagonist is cursed to be deprived of sleep and is eventually destroyed by Jupiter!

Sung by one of the greatest mezzo's of all time:
YouTube
 
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^^ Well that put a sudden stop to this thread, didn't it? :eek:

That would've been a shame!

Justin Vernon, the main man (and voice) behind Bon Iver - An American folk sort-of orchestra band, went through years of depression and whilst on a boat-trip in some asian country, where he tried to find meaning in life, he took out his recorder and sang "It might be over soon".

About a year later the first single to the new album came out:
Bon Iver - 22 (OVER S∞∞N)

If you wanna hear pain. You can also listen to his cover of Bonnie Ratt - I Can't Make You Love Me. That stuff is real... (It starts at 4:10)