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How about really really sad songs?

'Mother', by John Lennon.
Song tears me up every time I hear it.
The lyrics are simple and sparse, coupled with the pain in his voice, tears me up.
It helps if you already know the sad upbringing he had.

Father left when he was a baby. His mother gave him away to her sister to raise when he was a toddler. But as a young teen when he started to reconnect with his mother ( she taught him his first chords), she died.

The chorus, I'm getting teared up just thinking about it.
 
They bought a round for the sailor
And they heard his tale
Of a world that was so far away
And a song that we'd never heard
A song of a little bird
That fell in love with a whale


He said, 'You cannot live in the ocean'
And she said to him
'You never can live in the sky'
But the ocean is filled with tears
And the sea turns into a mirror
There's a whale in the moon when it's clear
And a bird on the tide


Please don't cry
Let me dry your eyes


So tell me that you will wait for me
Hold me in your arms
I promise we never will part
I'll never sail back to the time
But I'll always pretend you're mine
Though I know that we both must part
You can live in my heart


Please don't cry
Let me dry your eyes


And tell me that you will wait for me
Hold me in your arms
I promise we never will part
I'll never sail back to the time
But I'll always pretend that you're mine
I know that we both must part
You can live in my heart


Tom Waits, "Fish & Bird"
 
The one I copied the lyrics to was "One" by Metallica. I always thought it was a bit sad, but when I searched the lyrics with meaning it got even worse.

Apparently it's about a soldier who loses all his limbs and senses after a landmine goes off; his brain's still "alive," but nothing's really connected to it. So, pretty sad so far. But, apparently it's based on a movie, and the soldier in question starts shaking on the bed until doctors realize he's spelling "K-I-L-L-M-E" in morse code. The idea of just being locked inside your own head with no way to really communicate with others was always really sad/scary to me.

I can't remember anything
Can't tell if this is true or dream
Deep down inside I feel the scream
this terrible silence stops me
Now that the war is through with me
I'm waking up I can not see
That there's not much left for me
Nothing is real but pain, now

Hold my breath as I wish for death
Oh please God,wake me

Back in the womb it's much too real
In pumps life that I must feel
but can't look forward to reveal
Look to the time when I'll live
Fed through the tube that sticks in me
Just like a wartime novelty
Tied to machines that make me me
Cut this life off from me

Hold my breath as I Wish for death
Oh please God, wake me

Now the world is gone I'm just one
Oh God, help me

Hold my breath as I wish for death
Oh please God, help me

Darkness

Imprisoning me
All that I see
Absolute horror
I cannot live
I cannot die
Trapped in myself
Body my holding cell

Landmine

Has taken my sight
Taken my speech
Taken my hearing
Taken my arms
Taken my legs
Taken my soul
Left me with life in Hell

The movie is based on a book called 'Johnny Got His Gun' by Dalton Trumbo. I'd recommend it as a good read.
 
Paul McCartney's "Here Today." It's a song for Lennon. It's beautiful but a real tear-jerker.

Bob Dylan's "Shooting Star."

Tegan & Sara's "Call it Off" and "Now I'm All Messed Up." Anyone who has had failed relationships or missed opportunities will connect with these songs.
 
I can't believe no one has said it yet, so I will...

... anything in the key of Dm, the saddest of all keys.


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I've always found Tracy Chapman's "Bang Bang Bang" to be exceptionally sad and poignant.

Though I admit that due to an event in my childhood where my girlfriend murdered her mother, I'm more sensitive to the general theme of the song than the average person. It gets me every time.


"Bang Bang Bang"

What you go and do
You go and give the boy a gun
Now there ain't place to run to
Ain't no place to run to

When he hold it in his hand
He feel mighty he feel strong
Now there ain't no place to run to
Ain't no place to run

One day he may come back
Repay us for what we've done
Then where you gonna run to
Where you gonna run

But one fine day
All our problems will be solved
Bang bang bang
We'll shoot him down

Give him drugs and give him candy
Anything to make him think he's happy
And he won't ever come for us
He won't ever come

But if he does
And if there's no one else around
Bang bang bang
We'll shoot him down

If he preys only on his neighbors
Brothers sisters and friends
We'll consider it a favor
We'll consider justice done

But if he comes for you or me
And we can place a gun in his hand
Bang bang bang
We'll shoot him dead

What you go and do
You go and give the boy a gun
Now there ain't no place to run to
Ain't no place to run

Now we'll all be at his mercy
If he decides to hunt us down
Cause there ain't no place to run to
Ain't no place to run

If he wants the chances that you took from him
And nothing that you own
Then there'll be no place to run to
There'll be no place to run

And if he finds himself to be
A reflection of us all
Bang bang bang
He'll shoot us down

Before you can raise your eyes to read
The writing on the wall
Bang bang bang
He'll shoot you down

Before you can bridge the gulf between
And embrace him in your arms
Bang bang bang
He'll shoot you down