As I am listening to Pearl Jam’s Last Kiss, I am thinking that this might be the saddest song I know.
I am not THAT well versed in music, but a song about killing your girlfriend in a car accident is way more sad than “he broke up with me”.
What is everyone else’s nominations?
30KFT by Assemblage 23.
Puff the Magic Dragon.
“At 17” Janis Ian
It’s been said before on this very forum, but I must nominate And the Band Played Waltzing Matilda.
From memory, so the lyrics may not be quite right:
Yesterday, When I Was Young-Roy Clark
The Pogues - The Old Main Drag
Keep Me In Your Heart by Warren Zevon (who was diagnosed with terminal cancer before recording this album, and died two weeks after its release).
Alan Parsons - The Very Last Time
He Stopped Loving Her Today.
The very first thing that comes to mind is “Lesson Number Eight,” from Stephen Sondheim’s musical Sunday in the Park with George. The speaker–the musicals main character, great-great-grandson of George Seurat–is mourning the death of his grandmother (and only relative) and his own growing alienation from the things that make life worth living. It’s beautiful and sad.
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Here it is.
Roy Orbison’s In the Real World. It’s not “she broke up with me”, but “we’re deeply in love, but there’s no way that it’s going to work out.” A very sad theme, made sadder due to some personal relevance for me.
Where’ve You Been? by Kathy Mattea. I dare you to listen to the whole song without tearing up.
ETA: Dammit, Blob!
Or maybe Yesterday, When I Was Young, as per running coach, above.
“I’ll Be Home for Christmas” - for the utterly unforced pathos. Not a word of loss or loneliness or havin’ dun wrong, but the final lyric will always choke a sob out of me.
“Father and Son” by Cat Stevens. They’re both right – and they’re both wrong, and can’t understand how their perceptions differ.
“Turn Around” by Malvina Reynolds is exquisitely sad.
Cat Stevens and Ronan Keating do a brilliant version of “Father and Son”. I can’t link it cause I’m on the wife’s IPad, and am not proficient with it.
Woody Guthrie 1913 Massacre.