The saddest song of all time

Anonymous
The Wreck of the Edmund Fitzgerald
Anonymous
Rainy Days and Mondays
Wind Beneath My Wings
Anonymous
Eva Cassidy singing "Wonderful World" as she knew she was dying of cancer.


Joey Ramone singing "Wonderful World" as he knew he was dying of cancer. (OK, he didn't play it as sad.)

Warren Zevon's entire album about knowing he was dying of cancer. (Keep Me In Your Heart For Awhile ....)
Anonymous
Anonymous wrote:One Tin Soldier


As a kid this would make me very sad.
Anonymous
Cat's in the Cradle always makes me weepy. Also love Eva Cassidy's Fields of Gold.
Anonymous
Dixie Chicks' "Travelin' Soldier." Tears every single time. And then my daughter asked about it.
Anonymous
Time in a Bottle by Jim Croce.

He wrote it when his wife was pregnant with his son. He died three years later in a plane crash.
Anonymous
Anonymous wrote:The Wreck of the Edmund Fitzgerald


+1

Gordon Lightfoot also did an amazing version of Farewell to Nova Scotia which is a pretty melancholy song also

Anonymous
Thank you for sharing that -- I love Gordon Lightfoot and this song is great! I'm from Michigan so I've always had a soft spot for the Edmund Fitzgerald.
Anonymous
And I'm Telling You I'm Not Going....from "Dreamgirls".

Both the original Jennifer Holliday version and the Jennifer Hudson version from the film.

Sob, sob, sob,
Anonymous
Jesus is on the Wire by Thea Hopkins, about Matthew Shepard
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