Did you hear that lonesome whippoorwill?
He sounds too blue to fly
The midnight train is whining low
I’m so lonesome, I could cry

I’ve never seen a night so long
When time goes crawling by
The moon just went behind a cloud
To hide its face and cry

Did you ever see a robin weep
When leaves begin to die?
That means he’s lost the will to live
I’m so lonesome, I could cry

The silence of a falling star
Light’s up a purple sky
And as I wonder where you are
I’m so lonesome, I could cry

This has sometimes been called the saddest song ever written. Though Monday night when I was at a kirtan with Radhanath Swami he announced that a plane had crashed in Nepal, and 8 devotees had left their bodies, including 7 known to him from his home temple in Chowpatty, one of them a child.

He dedicated the kirtan to them and the start of that kirtan was pretty sad.

Naturally Hank Williams sings this song best.

It is a country standard, so you can hear any number of versions, including this one by Jimmie Dale Gilmore.

Even rockers take it on occasionally. Here is a version by Volbeat.

And who could sing any song more sadly than the Cowboy Junkies.

The bagpipes by themselves tend to sadness. Here is a version by Me First and the Gimmes with bagpipes.

Here Electric Black does a version with animation that “focuses on the sentiment of modern alienation captured by the song.”