The 50 Saddest Songs Of All Time

[Joachim Kettner]

Was his name Tom Slocum? He's mentioned quite a lot in Gene's biography.

[Richard Wilhelm]

I remember now, it was Buddy Lee. Once I saw the Burrito's at the Troubadour in West Hollywood, you could hear harmonica playing in the back room between sets. That was Gene. Another time I was there for the Burrito's, Janis Joplín was standing near me. I saw Gene play a couple of times at Gram Parson's tributes at the Palomino. I did see Gene once in Northern California at a club in Cotati. He had a band with Thomas Jefferson Kaye and he was living in Mendocino. The two Dillard and Clark albums are the greatest. Bluegrass that has spirituality, sadness and joy, just the way it should be.

[Brett Day]

I Don't Go Around Mirrors
Honey
I'm So lonesome I Could Cry
He Stopped Loving Her Today
The Red Sovine Song about the boy and trucker. The title escapes me
Phantom 109

"Phantom 309". There's great steel work on that song too

[Brett Day]

Roy Orbison's song, "In Dreams sounds sad because when Roy sings the part where it says, "But just before the dawn, I awake to find you're gone, and the orchestra plays a sad part. "I'm So Lonesome I Could Cry" is definitely a sad song, and there's an instrumental version I heard in the '90s by a dulcimer player named David Schnaufer and it was beautiful, but sad.

[Calvin Walley]

Not a Red Sovine song on the list??

it doesn't get any sadder than "teddy bear "

[Dustin Kleingartner]

They had to put a Townes song on there for sure, and Waitin' Around to Die is a pretty sad song, but I think his saddest song is Marie.
Spoiler alert, he's homeless, can't get a job or welfare, and then his pregnant girlfriend dies and he catches a southbound train on the fly. Just devastating.

[Glenn Suchan]

They had to put a Townes song on there for sure, and Waitin' Around to Die is a pretty sad song, but I think his saddest song is Marie.
Spoiler alert, he's homeless, can't get a job or welfare, and then his pregnant girlfriend dies and he catches a southbound train on the fly. Just devastating.

Dustin, I agree that "Marie" just might be TVZ's saddest song. It's my favorite of his. I first heard "Marie" late at night, on the radio while driving home from a gig. It haunted me until I was able to track down the album on which it first appeared - his 1994 release, (No Deeper Blue) which I immediately bought. "Marie" also appears on Townes' post humous, 2001 release, Live at McCabe's. That version is solo and is, IMO his best version.
Here's that recording:
https://www.youtube.com/watch?v=Lk-zKjfO2E8

and the full band version from No Deeper Blue:
https://www.youtube.com/watch?v=CJAqt_FTasc

Also from No Deeper Blue are other equally sad and beautiful songs:
"A Song For":
https://www.youtube.com/watch?v=BYK-jNZ0xhQ

and his really spooky song about addiction, "The Hole":
https://www.youtube.com/watch?v=_uvtGIBV4Kc

Townes Van Zandt, one of the greatest of Texas song writers. RIP Townes.
He will be gone 19 years this coming New Year's Day.

Keep on pickin'!
Glenn

[Steve Allison]

"Get The Hammer Momma there's a Fly ON Babies Head". The Hoosier Hot Shots. Purty Damn sad to me!

[Richard Wilhelm]

'Old Blue'...'Early Morning Rain'...'Darcey Farrow...Gram Parson's 'Do you know how it feels'...'Green grass of Home'. But Tim Hardin's 'Tribute to Hank Williams'..has got to be one of the sadest

Goodby, Hank Williams my friend
I didn't know you...
But I've been to places you're been

In Richmond, where they'd had just been
For some, seats could not be found
But they planned to see him again
Next time..Hank Williams..
Came to town

Hardley no body knew that night
How soon they'd be crying
Hardly no body knew that night
That Hank Williams...was dying

He sang from his heart
Took the pain for his fans
Who watch the pain in his heart
And they sat, and then...
They clapped their hands.

Good bye Hank Williams, my friend
I didn't know you...
But I've been to places you've been

The chauffeur steared the car that
night
To a town next in line for a show
With his name, and the date in lights
And the people, with tickets, to go.

Hardley no body knew that night
How soon they're be crying
Hardly no body knew that night
Hank Williams...Was dying

Goodbye Hank Williams, my friend
I did'nt know you
But I've to places you're been
-
the 'live' version (Tim Hardin in Concert) flips the first and second verses, and replaces the third:

Whisky took the heart break
From too many broken dreams
What pain wasn't taken by the Whisky
Was given by too much morphine

[Richard Wilhelm]

'Old Blue'...'Early Morning Rain'...'Darcey Farrow..Gram Parson's 'Do you know how it feels'...'Green grass of Home'. But Tim Hardin's 'Tribute to Hank Williams'..had got to be one of the sadest

Goodby, Hank Williams my friend
I didn't know you...
But I've been to places you're been

In Richmond, where they'd had just been
For some, seats could not be found
But they planned to see him again
Next time..Hank Williams..
Came to town

Hardley no body knew that night
How soon they'd be crying
Hardly no body knew that night
That Hank Williams...was dying

He sang from his heart
Took the pain for his fans
Who watch the pain in his heart
And they sat, and then...
They clapped their hands.

Good bye Hank Williams, my friend
I didn't know you...
But I've been to places you've been

The chauffeur steared the car that
night
To a town next in line for a show
With his name, and the date in lights
And the people, with tickets, to go.

Hardley no body knew that night
How soon they're be crying
Hardly no body knew that night
Hank Williams...Was dying

Goodbye Hank Williams, my friend
I did'nt know you
But I've to places you're been
-
the 'live' version (Tim Hardin in Concert) flips the first and second verses, and replaces the third:

Whisky took the heart break
From too many broken dreams
What pain wasn't taken by the Whisky
Was given by too much morphine

[Dom Franco]

Billie Holiday's "Strange Fruit"

[Skip Edwards]

"Cottage For Sale"...a few pages back is a good choice.
But, since it's that time of year, my vote goes down as a tie between "I'll Be Home For Christmas", and "Auld Lang Syne".