I’d have to say Natural Blues by Moby and Hurt by nine inch nails. NB just has a very sad melody to it along with it’s African American Gospel sounding voice, and Hurt sounds like someone pleading their case to the world before suicide.
easily the saddest most depressing song I know is
“Dinner with Ivan” by Big Head Todd and the Monsters.
It’s on their second album, on their own indie label.
But another really depressing one is “Where I went wrong” by the Poppy Family:
That’s Where I Went Wrong
Poppy Family
This old road
I don’t know where it leads
And I don’t care
Cause it’s not hard for me to see
That when it ends
There’ll be nothing left for me
Cause the only thing I care about
I’ve got to live without
This bus is awful cold
We’ve gone so many miles
God, please help me go to sleep
and forget him for a while
I know it’s not his fault
I’ve known it all along
I was the one that trusted him
That’s where I went wrong
Two choices off the top of my head, both by Cowboy Junkies: The Last Spike: A woman learns that the small town she lives in is losing its rail line. This means that (a) the town itself is going to close down and (b) her dreams of her husband returning on the train are gone.
“Mornings seem so damn sad these days without the call of the 8:15. Looks like this town is finally going to die away, leaving nothing but broken promises where there once was small town dreams. And I’ve watched the flatcars take away our timber. I’ve watched the coalcars steal our rock. And now that we’ve got nothing left to take we’re told that the TV station will be closing, Main Street windows will be boarded – and that this foolish dream must stop.”
Witches woman hears the call of the witches to come join them. Doesn’t want to go. Turns to her lover for support and finds him asleep.
“But under spell of deep sleep, you moans and turn away; taking your protection and my desire to stay. So I rise to the hills. I ride the night winds. I make love to the darkness and I laugh at man’s sins.”
The line “and freedom, oh, freedom, well that’s just some people talkin’, you’re prison is walkin’ through this world all alone” is among of the saddest lines I’ve heard in a song. Thankfully, though, the song has a positive and truthful message, i.e., that the “queen of hearts is always your best bet”.