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Sad, but Beautifully Written Songs

OK, if we are going to include Classical, then the Barber Adagio for Strings gets my vote FTW.

OP referred to Beautifully Written Songs, without a specific genere. I love all kind of music, but to be honest, rock does not touch my soul; I like it , I listen it every day and I really enjoy it, but does not take me anywhere . But when I listen to this Bach master piece, is like my soul separate from my body and join the notes :)...
 
"Gone Away" - Offspring (Reminds me of a good friend of mine who passed away a few years ago)

"Don't Stop this Train" - John Mayer (Parents recently divorced, gets me thinking of how it used to be and how it could be today.)

I love both songs but I cannot and will not listen to them.
 
The black dahlia murder, Deathmask Divine
Removal of the eyes gives my heart a saddened chill
I preserve them in formaldehyde to gaze upon at will
How their greenish flecks befell me that starlit winter's night
I lost all that I ever was while locked within their sight

Before you sits a broken man, your fragile pinkish heart in hand
Peculiar how it can hurt so bad while love is only in the mind
I sew the gaping chestwound, each thread is made with love
The bosom where I would rest my face is covered in your blood


No
This is not the end,
You'll live on eternally
Oh
Lord it's not the end,
My secret you'll forever be

I interrupt this transformation, A familiar lust swelling in me
A long and soulful kiss, the shades are drawn, the living world can't see
The coil of entrails, how curious the smell, so pungent to my eager nostrils
Hands further compelled

No
It's not the end
Forever you'll be in my arms.

I could never let you go
My darling, cold and blue
I wonder are you dreaming still
Spread eagled, blood removed

I weave the sucking trocar
beneath your bruising skin
tonight I'll lay beside you darling
In necromantic sin

(solo)

Pinned to the bed sheets like a priceless butterfly you're mine
I hear your voice, so precious, echoing deeply inside
I did my best to love you while you did live and breathe
This tender taxidermy trophy of the bereaved.

I could never let you go
My darling, cold and blue
I wonder are you dreaming still
Spread eagled, blood removed

I weave the sucking trocar
beneath your bruising skin
tonight I'll lay beside you darling
In necromantic sin
 
The saddest song I've ever heard is Warren Zevon - Keep me in your Heart


Otherwise
Gordon Lightfoot - Wreck of the Edmund Fitzgerald (this wasn't mentioned yet!)
Alice in Chains - Private Hell
Johnny Cash's version of Hurt or The Wall live version off of Folsom
Eddie Veddar - Society (off of Into the Wild)
Richard Thompson - Treadwell No More (off of Grizzly man soundtrack)