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The saddest song..

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mee-kay-la:
"Mountain Jam"--- Allman Brothers
"Jane Says" --- Jane's Addiction
"Heroin" --- Velvet Underground.
"Wooden Ships" --- Crosby, Stills, Nash and Young.

There are more.

theMOTIVe:
Do you remember - Jack Johnson



Damn. Thats a good one.

EDIT: MORE!!!

Imagine- A Perfect Circle
Beautiful World- RATM (they really mellowed out on that one)
Fred Jones, Part 2 / The Ascent of Stan / The Luckiest - Ben Folds
No Woman, No Cry- Bob Marley
Sway - Lostprophets
Let Go- Frou Frou
Elanor Rigby- The Beatles
This Will Be Laughing Week- The Ultimate Fakebook
Stumbeline - Smashing Pumpkins
Rob Dougan- Clubbed to Death
Damien Rice- Cannonball
Bend the Bracket- Chevelle

Kai:
Speaking of the Allman Brothers; Blue Sky strikes me as particularly sad. Not sure why.

Gryff:
Bright Eyes "We Are Nowhere And It's Now"

Emmylou Harris has a voice that could make anyone cry. What a singer! As a backing vocalist she is absolutely unsurpassed.

Jeridus:
For some reason, Arcade Fire - In The Back Seat strikes me as sad... probably just all the lamenting wailing going on

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