Hard to tell - there are so many sad songs.
I like Johnny Cash's version of Lemur's very first suggestion.
Two songs that I think are extremely depressing are from Lou Reed's "Magic & Loss" album.
Cremation deals with the loss of a friend.
Well the coal black sea waits for me me me
The coal black sea waits forever
The waves hit the shore
Crying more more more
But the coal black sea waits forever
The tornados come up the coast they run
Hurricanes rip the sky forever
Through the weathers change
the sea remains the same
The coal black sea waits forever
There are ashes split through collective guilt
People rest at sea forever
Since they burnt you up
Collect you in a cup
For you the coal black sea has no terror
Will your ashes float like some foreign boat
or will they sink absorbed forever
Will the Atlantic Coast
have its final boast
Nothing else contained you ever
Now the coal black sea waits for me me me
The coal black sea waits forever
When I leave this joint
at some further point
The same coal black sea will it be waiting
Harry's Circumcision - an account of complete unhappiness in a person's life
Looking in the mirror Harry didn't like what he saw
The cheeks of his mother the eyes of his father
As each day crashed around him the future stood revealed
He was turning into his parents
The final disappointment
Stepping out of the shower Harry stared at himself
His hairline receding the slight overbite
He picked up the razor to begin his shaving
and thought oh I wish I was different
I wish I was stronger I wish I was thinner
I wish I didn't have this nose
These ears that stick out remind me of my father
and I don't want to be reminded at all
The final disappointment
Harry looked into the mirror thinking of Vincent Van Gogh
and with a quick swipe lopped off his nose
And happy with that he made a slice where his chin was
He's always wanted a dimple
The end of all illusion
Then peering down straight between his legs
Harry thought of the range of possibilities
A new face a new life no memories of the past
and slit his throat from ear to ear
Harry woke up with a cough the stitches made his wince
A doctor smiled at him from somewhere across the room
Son we saved your life but you'll never look the same
And when he heard that, Harry had to laugh
Although it hurt Harry had to laugh
The final disappointment
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