Mickey Newbury has many, and wrote many for others. By far, the saddest album of all time is "Frisco Mabel Joy." I don't think there's a single song on it that wouldn't be a candidate for this thread.
An American Trilogy
How Many Times (Must The Piper Be Paid For His Song)
The Future's Not What It Used To Be
Mobile Blue
Frisco Depot
You're Not My Same Sweet Baby
Remember The Good
Swiss Cottage Place
How I Love Them Old Songs

In my opinion, nothing is sadder than the title track, "San Francisco Mabel Joy." Driving alone in my truck, in moments of Low T I suppose, I've cried to this.

Enjoy, or cry. Take a listen.
Steve.


"I was a deerhunter long before I was a man." ~Gene Wensel's Come November (2000)
"A vote is like a rifle; its usefulness depends upon the character of the user." ~Theodore Roosevelt