Desperados Waiting for a Train Lyrics
And he'd sit out in the kitchen and cry
And run his fingers through seventy years of livin'
And wonder, "Lord, has ever' well I've drilled run dry?"
Like desperados waitin' for a train
Like desperados waitin' for a train
And an old school man of the world
He let me drive his car
When he's too drunk to
And our lives were like some old western movie
Like desperados waitin' for a train
Like desperados waitin' for a train
To a bar called the Green Frog Cafe
There were old men with beer guts and dominos
Lying 'bout their lives while they'd played
They all called his "Sidekick"
Like desperados waitin' for a train
Like desperados waitin' for a train
And there's brown tobacco stains all down his chin
To me he's one of the heroes of this country
So why's he all dressed up like them old men
Like desperados waitin' for a train
Like desperados waitin' for a train
I was grown and he was almost gone
So we just closed our eyes and dreamed us up a kitchen
And sang another verse to that old song
"Come on, Jack, that son of a bitch is comin' "
Like desperados waitin' for a train
Like desperados waitin' for a train
Like desperados waitin' for a train

One of the best country/folk songs ever written. Why does this not have any comments?
Lyrics are self-explanatory. It's about a young boy and his relationship with an old man, who share an incredible mutual respect for eachother. The boy listens to the stories the man has about his hard life, and the man teaches the boy many things about growing up like driving, gambling and chasing girls.
The boy can't understand why this man, who he respects more than no other, did not lead an overly successful life, and rather winds up a rugged old man with tobacco stains on his chin wearing worn down clothes.
The man finally dies, and they mutually hope that his death will provide him the success and happiness the old man deserves.
Actually, Guy Clark based this song on an old man he knew as a "grandfather figure" as a youth down in Texas. Willie Nelson's solo video (as seen on YouTube) is about the best visual representation of this great song as you'll ever see.
Actually, Guy Clark based this song on an old man he knew as a "grandfather figure" as a youth down in Texas. Willie Nelson's solo video (as seen on YouTube) is about the best visual representation of this great song as you'll ever see.

I was so damn shocked to see that this song only had one comment. Such an amazing song!

This song is about Guy's grandmother's boyfriend and Guy's relationship to him.
It seems to me that the lyrics reflect a type on man with a sort of desperado style bravaura, but without a sense of purpose or direction. Machismo without an outlet, like <insert song title>.
There's perhaps some sort comparison here, the old man is waiting for death, the young man waits to have his life.