For me, this one's easy..."Waiting Around to Die" by the late great Townes Van Zandt is the saddest song ever written. Unfortunately, Townes' life was not too far from the lyrics of the song. He struggled with mental illness and addiction for most of his life. Also had a huge gambling problem, which usually left him destitute. He's not as well-known as he should be, though he did write "Pancho and Lefty" which was a huge hit for Willie Nelson & Merle Haggard and has even been covered by Bob Dylan in recent years. Steve Earle was once quoted as saying "Townes Van Zandt is the greatest songwriter ever, and I'd stand on Bob Dylan's coffee table and tell him that." When Townes heard that quote, his response was classic: "Well, I've met Bob's bodyguard, and if Steve thinks he can stand on his coffee table, I'm afraid he's mistaken." I'd encourage all who haven't heard of the guy to look into him...listen to his songs...help keep his legacy alive.
Anyway, here's the lyrics to "Waitin' Around to Die"...if anyone knows a sadder song, I'd love to hear it (or maybe not)
Sometimes I don't know where this dirty road is taking me
Sometimes I can't even see the reason why
I guess I keep on gamblin', lots of booze and lots of ramblin'
It's easier than just a-waitin' 'round to die
One-time friends I had a ma, I even had a pa
He beat her with a belt once cause she cried
She told him to take care of me, she headed down to Tennessee
It's easier than just a-waitin' 'round to die
I came of age and found a girl in a Tuscaloosa bar
She cleaned me out and hit it on the sly
I tried to kill the pain, I bought some wine and hopped a train
Seemed easier than just a-waitin' 'round to die
A friend said he knew where some easy money was
We robbed a man and brother did we fly
The posse caught up with me, drug me back to Muskogee
It's two long years, just a-waitin' 'round to die
Now I'm out of prison, I got me a friend at last
He don't steal or cheat or drink or lie
His name's codeine, he's the nicest thing I've seen
Together we're gonna wait around and die