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Saddest Song I Ever Heard

The Little Girl by JMM

To Daddy by Dolly Parton, also sung by Emmylou Harris

Me and Little Andy by Dolly Parton
 
Ooohh... Seven Spanish Angels is a good one!

I have to add "Sometimes it Snows in April" by Prince and "Gone To Soon" by Michael Jackson, though I won't comment on the irony of it being dedicated to a kid who died of AIDS.

Just remembered "Fast Car" - Tracy Chapman

Alabama - John Coletrane
Don't Explain - Nina Simone
I Grieve - Peter Gabriel from the soundtrack to City of Angels, good Lord that one gets to me!
 
Christmas Shoes

Calling All Angels from Pay it Forward

Watch the Lamb by Ray Boltz

Via Dolorosa by Sandi Patti
 
Tim McGraw

"Don't Take the Girl"

Johnny’s daddy was taking him fishin’
When he was eight years old
A little girl came through the front gate holdin’ a fishing pole
His dad looked down and smiled, said we can’t leave her behind
Son I know you don’t want her to go but someday you’ll change your mind
And johnny said take jimmy johnson, take tommy thompson, take my best friend bo
Take anybody that you want as long as she don’t go
Take any boy in the world
Daddy please don’t take the girl

Same old boy
Same sweet girl
Ten years down the road
He held her tight and kissed her lips
In front of the picture show
Stranger came and pulled a gun
Grabbed her by the arm said if you do what I tell you to, there won’t be any harm
And johnny said take my money, take my wallet, take my credit cards
Here’s the watch that my grandpa gave me
Here’s the key to my car
Mister give it a whirl
But please don’t take the girl

Same old boy
Same sweet girl
Five years down the road
There’s going to be a little one and she says it’s time to go
Doctor says the baby’s fine but you’ll have to leave
’cause his momma’s fading fast and johnny hit his knees and there he prayed
Take the very breath you gave me
Take the heart from my chest
I’ll gladly take her place if you’ll let me
Make this my last request
Take me out of this world
God, please don’t take the girl

Johnny’s daddy
Was taking him fishin’
When he was eight years old
 
I cant belive I forgot this one...

Aeris Theme from Final Fantasy 7. Never has a videogame had such a heart rending song. And especially as it occurs during perhaps THE most dramatic moment in the game...god its sad
 
Roy Orbison was notorious for his sad songs. Here's one of the saddest. It's on his "Mystery Girl" album...

"A Love So Beautiful", by Jeff Lynne & Roy Orbison

The summer sun looked down on our love long ago
But in my heart I feel the same old afterglow
A love so beautiful... in every way
A love so beautiful... we let it slip away

We were too young to understand to ever know
that lovers drift apart and that's the way love goes
A love so beautiful... a love so sweet
A love so beautiful... a love for you and me

And when I think of you
I fall in love again

A love so beautiful... in every way
A love so beautiful... we let it slip away...
 
Tree of Hearts by Brian White

Two Teardrops by Steve Wariner

Holes in the Floor of Heaven by Steve Wariner

Angel Flying too close to the ground written by Willie Nelson

Please Remember Me and Angry All the Time by Tim McGraw

Is Heaven Good Enough For You and Cold, Cold Earth by Allison Moorer
 
featherfingers said:
Roy Orbison was notorious for his sad songs. Here's one of the saddest. It's on his "Mystery Girl" album...

"A Love So Beautiful", by Jeff Lynne & Roy Orbison

The summer sun looked down on our love long ago
But in my heart I feel the same old afterglow
A love so beautiful... in every way
A love so beautiful... we let it slip away

We were too young to understand to ever know
that lovers drift apart and that's the way love goes
A love so beautiful... a love so sweet
A love so beautiful... a love for you and me

And when I think of you
I fall in love again

A love so beautiful... in every way
A love so beautiful... we let it slip away...

I love that song too!!
 
Someone mentioned "My Immortal" By Evanescense.. its a great song if its the original on the album.. not the radio version. The original version is nothing but piano, which really puts the song into the 'sad' category.

One of my all time sad songs is "Something I Can Never Have" By Nine Inch Nails.
 
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