“I love a good man outside the law, just as much as I hate a bad man inside the law,” Woody Guthrie once wrote on a lyric sheet for his song “Pretty Boy Floyd.”
The tale of Charles Arthur “Pretty Boy” Floyd must have appealed to Guthrie. Floyd was an Oklahoma native who turned to bank robbing and violence in the 1920s as the country faced economic difficulty.
Floyd’s exploits were well known during the era, and Guthrie, eight years younger than Floyd, would have likely followed the outlaw’s story in newspapers and local gossip.
By the time Guthrie wrote his outlaw ballad in 1939, Pretty Boy Floyd had been dead some five years, though his story must have seemed as relevant to Guthrie as other topical subjects like the Grand Coulee Dam or the USS Reuben James.
Guthrie turns Floyd’s story into a Robin Hood tale of good versus evil. A thief steals from the rich banker to give to the poor farmer, though one finds little evidence to support this benevolent version of the real Pretty Boy Floyd.
Floyd was best known for his part in the June 1933 Kansas City Massacre, a scheme to free the prisoner Frank Nash, who was arriving in Kansas City in FBI custody by train from Hot Springs, Arkansas. Floyd and his cohorts opened fire as FBI agents and police officers escorted Nash from Union Station to a car parked out front, in the end killing several agents as well as Nash.
By 1933, the 29-year-old Floyd was already a fugitive from the law, wanted for a St. Louis highway robbery and an Ohio bank robbery, among other crimes. He had arrived in Kansas City by way of escaping transport to the Ohio State Penitentiary.
Guthrie completely washes over Floyd’s criminology report. In Guthrie’s telling, Floyd simply shoots down a rude deputy then is wrongfully accused of “every crime in Oklahoma .”
The song contains one of Guthrie’s most famous lines on the subject of crime and money: “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.”
Another notable version of “Pretty Boy Floyd” was cut by The Byrds for their 1968 album, Sweetheart of the Rodeo. The song was recorded in Nashville in March of that year with John Hartford on banjo.
Pretty Boy Floyd has continued to be a subject of fascination in popular culture, with portrayals in numerous gangster films, most recently in the Johnny Depp-helmed Public Enemies.
“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.
Written by Woody Guthrie