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What is the Saddest Song?



Goldenrod and the 4H stone
The things I brought you when I found out
You had cancer of the bone

Your father cried on the telephone
And he drove his car into the Navy yard
Just to prove that he was sorry

In the morning, through the window shade
When the light pressed up against your shoulderblade
I could see what you were reading

All the glory that the Lord has made
And the complications you could do without
When I kissed you on the mouth

Tuesday night at the Bible study
We lift our hands and pray over your body
But nothing ever happens

I remember at Michael's house
In the living room when you kissed my neck
And I almost touched your blouse

In the morning at the top of the stairs
When your father found out what we did that night
And you told me you were scared

All the glory when you ran outside
With your shirt tucked in and your shoes untied
And you told me not to follow you

Sunday night when I cleaned the house
I found the card where you wrote it out
With the pictures of your mother

On the floor at the great divide
With my shirt tucked in and my shoes untied
I am crying in the bathroom

In the morning when you finally go
And the nurse runs in with her head hung low
And the cardinal hits the window

In the morning in the winter shade
On the first of March, on the holiday
I thought I saw you breathing

All the glory that the Lord has made
And the complications when I see His face
In the morning in the window

All the glory when He took our place
But He took my shoulders and He shook my face
And He takes and He takes and He takes


"Tears in Heaven" by Clapton, especially if you consider the heartbreaking moment in Clapton's life when he wrote it. I can't think of anything more gut-wrenching.
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These are the ones that have all the feels for me:

Porcupine Tree - Collapse the Light Into Earth
Steven Wilson - Routine
Kasey Musgraves - Rainbow


This one is pretty sad.

But it's hard to get much sadder than a cluster of songs about generations of family dysfunction.



Silver Supporting Member
Hear that lonesome whippoorwill
He sounds too blue to fly
That means he's lost the will to live
I'm so lonesome I could cry
Did you ever see a night so slow
As time goes draggin' by
The moon just went behind the clouds
To hide its face and cry
The silence of a falling star
Lights up a purple sky
And as I wonder where you are
I'm so lonesome I could cry
I'm so lonesome I could cry
I'm so lonesome I could cry

Hank Williams


Silver Supporting Member
I saw Daniel Johnston live once and there were moments where I had to maintain composure, nearly started crying. His songs and lyrics are heart wrenching. Dude was a master at conveying subjects like heartache and unrequited love with deceptively simple, yet profoundly poetic prose. I haven't thought about or listened to him in awhile. This thread reminded me that I should.

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