Woody Guthrie was an incredibly prolific songwriter, composing thousands of songs in his lifetime. Many of these, like "The Sinking Of The Reuben James," were based on events that Guthrie read about in news articles. It's likely that Guthrie came across the story of an outlaw named Pretty Boy Floyd, which provided material for this song. Anna Canoni, who is Guthrie's granddaughter, explains: "'Pretty Boy Floyd' is one of Woody's more popular ballads. The outlaw who helped the poor, a Robin Hood story. What Woody would do, he would take newspapers read through the articles and write songs about stories that touched him.
"Pretty Boy Floyd"
If you'll gather 'round me, children
A story I will tell
'Bout Pretty Boy Floyd, an outlaw
Oklahoma knew him well
It was in the town of Shawnee
A Saturday afternoon
His wife beside him in his wagon
As into town they rode
There a deputy sheriff approached him
In a manner rather rude
Vulgar words of anger
An' his wife she overheard
Pretty Boy grabbed a log chain
And the deputy grabbed his gun
In the fight that followed
He laid that deputy down
Then he took to the trees and timber
To live a life of shame
Every crime in Oklahoma
Was added to his name
But a many a starving farmer
The same old story told
How the outlaw paid their mortgage
And saved their little homes
Others tell you 'bout a stranger
That come to beg a meal
Underneath his napkin
Left a thousand dollar bill
It was in Oklahoma City
It was on a Christmas Day
There was a whole car load of groceries
Come with a note to say
Well, you say that I'm an outlaw
You say that I'm a thief
Here's a Christmas dinner
For the families on relief
Yes, as through this world I've wandered
I've seen lots of funny men
Some will rob you with a six-gun
And some with a fountain pen
And as through your life you travel
Yes, as through your life you roam
You won't never see an outlaw
Drive a family from their home
A story I will tell
'Bout Pretty Boy Floyd, an outlaw
Oklahoma knew him well
It was in the town of Shawnee
A Saturday afternoon
His wife beside him in his wagon
As into town they rode
There a deputy sheriff approached him
In a manner rather rude
Vulgar words of anger
An' his wife she overheard
Pretty Boy grabbed a log chain
And the deputy grabbed his gun
In the fight that followed
He laid that deputy down
Then he took to the trees and timber
To live a life of shame
Every crime in Oklahoma
Was added to his name
But a many a starving farmer
The same old story told
How the outlaw paid their mortgage
And saved their little homes
Others tell you 'bout a stranger
That come to beg a meal
Underneath his napkin
Left a thousand dollar bill
It was in Oklahoma City
It was on a Christmas Day
There was a whole car load of groceries
Come with a note to say
Well, you say that I'm an outlaw
You say that I'm a thief
Here's a Christmas dinner
For the families on relief
Yes, as through this world I've wandered
I've seen lots of funny men
Some will rob you with a six-gun
And some with a fountain pen
And as through your life you travel
Yes, as through your life you roam
You won't never see an outlaw
Drive a family from their home
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