Desperado - Eagles
Ryan's Song - Phil Keaggy (written for his son, who died 3 days after being born)
And as mentioned, Wreck of the Edmund Fitzgerald, while not the saddest song I've heard, definitely the most chilling. The damn song sounds eerie, if you close your eyes you'd swear you were on a boat. Damn creepy.
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Nothing like rediscovering one of the greatest bands ever!
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