Saddest Songs

“Me and Bobby McGee”. One line stands out to me as extremely sad . . . “I'd trade all of my tomorrows, for a single yesterday.”

Along with the opening lines of that verse "somewhere near Salinas, I let her slip away...".

That opening line haunted me for years as I replayed all my relationship failures after my first wife died (including my shortcomings with her).

The good news is I got back to one I let slip away 40+ years ago for reasons I still don't understand. She's sleeping soundly down the hall right now. Feel like I got some of those tomorrows back :)
 
This one always gets me. Practically had it on a loop after the first wife died. Thankfully, I was able to drop it from my playlists a few years back.

 
Some probably find this too sappy, but I've always liked it.



This is an English adaptation of a 1961 song by Jacques Brel, a well-known Belgian singer-songwriter. The original song was titled "Le Moribond" (The Dying Person).

Jacques Brel also wrote "Ne me quitte pas" (Do not leave me) in 1959, which was adapted into "If you go away".

Jacques Brel had another song about death which I love, called "J'arrive" (I am coming) in 1968. Brel died of lung cancer in 1978, at the age of 49.
 
Townes VanZandt singing "waiting around to die" brings uncle Seymore to tears.


Someone asked Townes why he never played more happy songs ? He replied "These are my happy songs".
 
How about "Alone Again, Naturally" by Gilbert O'Sullivan?

Covid theme song for 2020.
 
I have two:
Somewhere Over the Rainbow
Comfortably Numb
 
From probably my favourite band The Pogues we have "Misty Morning, Albert Bridge"

"I awoke so cold and lonely
In a faraway place
The sun fell cold upon my face
The cracks in the ceiling spelt hell
Turned to the wall
Pulled the sheets around my head
Tried to sleep, and dream my way
Back to you again"


I also find the Jim Croce song "Time in a Bottle" sad.

"If I could make days last forever
If words could make wishes come true
I'd save every day like a treasure and then
Again, I would spend them with you
But there never seems to be enough time
To do the things you want to do
Once you find them"
 
I'm surprised no one has mentioned "Rainy Night in Georgia" by Brook Benton.

"Lord....I feel like it's raining all over the world."

 
2 for me....
The Long and Winding Road - Beatles
Use Somebody - Kings of Leon
 
The flood song by Aaron Neville reminded me of this -- Robert Plant's harp and vocal and Jimmy Page's repetitious slide work gives me a feeling of listless despair. Despite that, my favorite LZ song.

 
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There are many songs that are sad to me.

This one is a tough one for me to listen too as it to ms gamboolgal and I - it is our son, Jeffrey, who passed away unexpectedly a little over one year ago....

 
He was near passing when this video was done

His last album The Wind is all about end of life stuff. Dirty Life & Times, She's too good for me, Numb as a Statue. I didn't know much of Warren other than Werewolves of London (which I don't especially care for) I imagine Keep me in your heart is a song to his wife. Please stay is a song from his wife to him. As a fairly recent widower this one hits me right in the feels

 
Surprised no one has mentioned "Fire and Rain" by James Taylor. That seemed to be the "quintessential" sad song of the 1970s.
 
Townes VanZandt singing "waiting around to die" brings uncle Seymore to tears.


Someone asked Townes why he never played more happy songs ? He replied "These are my happy songs".


I read a youtube comment one time that said something like, "there is sad, there is painful, there is hopeless, and then there is Townes"


Video with Uncle Seymour.



youtube comment says: The black man was a walking blacksmith -- traveled from place to place with his tools to fix horses, other metallic items -- tools ( he could make them as well), railings, fences. His real name was Uncle Seymour Washington -- 1896-1979 RIP. Back in 1975, the director would've been smart to film an hour of Seymour's philosophy of life and not just the 5 minutes he did film. Interesting dude, I can see why Townes befriended him and took him along for his movie.


wiki states 1896-1977
 
This one, The Green Fields of France, would leave Barney the Purple Dinosaur crying in his beer. It's been recorded by numerous Celtic and folk musicians, but this version by the Furey Brothers and Davey Arthur, is probably best known. Name misspelled on the caption.


 
As others have posted, Clapton's Tears in Heaven, and Cash's cover of Hurt are definitely up there for me.

A very new release by Jason Isbell and the 400 Unit, Dreamsicle, is also a contender:

 
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