The saddest song in the world

Sad songs they say so much

LINK

Supposedly this masterpiece is the least-requested top ten pop hit (non novelty) on oldies radio.

The Way We Were - Barbra Streisand

This is right up there with the OP’s saddest.

Hank Williams as Luke the Drifter - Pictures from Life's Other Side

Truly macabre

quote:

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In the world's mighty gallery of pictures
Hang the scenes that're painted from life
There's pictures of love and of passion
And there's pictures of keys and of strife
There hung pictures of youth and of beauty
Of old age and a blushing young bride
They all hung on the wall but the saddest of all
Are the pictures from life's other side
Just a picture from life's other side
Someone has fell by the way
A life has gone out with the tide
That might have been happy some day
There's a poor old mother at home
She's watching and waiting alone
Just longing to hear from a loved one so dear
Just a picture from life's other side
The first scene is that of a gambler
Who had lost all of his money at play
And he drowses dead mother's ring from his finger
Which she wore long ago on her wedding day
It's his last earthly treasure but he stakes it
Then bows his head that his shame he might hide
But when they lifted his head they found he was dead
That's just a picture from life's other side
Now the last scene is that by the river
Of a heartbroken mother and baby
As the harbor lights shine and they shiver
On an outcast, soon no one will save
And yet she was once a true woman
She was somebody's darling and pride
God help her she leaps, oh there's no one to weep
It's just a picture from life's other side

---

The entire album is the saddest album of all time:

LINK

Although, Beyond the Sunset is staggeringly beautiful in its melancholy. Try not to cut onions if you can.

Hard to top the OP with context, but my best effort is:

These Are The Days Of Our Lives - Queen

Keep Me In Your Heart by Warren Zevon


He wrote this song knowing he was going to die after bring diagnosed with terminal cancer.. and I don't know, I'm pretty sure cancer has affected everyone in some way.. so it hits fricking real hard.

Anathema’s One Last Goodbye is the saddest song IMO

Maybe not the saddest, but No Time to Cry by Merle Haggard is pretty good.

My Chemical Romance - Cancer

LINK