Very nice article by Steve Jones. Here is Woody’s story about the song’s background, from his perspective as told to Alan Lomax. You can listen to Woody in his own recorded words on the Rounder Records box set, WOODY GUTHRIE: AMERICAN RADICAL PATRIOT.

This here one is about a outlaw that’s really come from about seventeen miles from where I was born and raised and I know people all through his section of the country and he knows people all through my section of the country and for years and years now, uh, well, for about four or five years, we won’t make it sound too ancient because he’s sort of a late name on the outlaw list, but he did make a name and he made a pretty name. Pretty Boy Floyd, they called him.

AL: Why was that anyway? Why did they call him Pretty Boy?

WG: His first name was Charles and they called him Pretty Boy. Pretty Boy was, uh, was a name that, he wasn’t the only guy in that country that got to be called “pretty boy”. I remember when these here bell bottom, balloon bottom britches first come out, ya know, and the boys started wearin’ them, uh, all around over the country. Why, eh, (laughs) when the first ones bought them and come walkin’ down the street, why, we had a habit of callin’, uh, hollerin’, “Hello, pretty boy” and, uh, Pretty Boy Floyd was, uh, sort of a mild-natured man, the way I hear it, sort of smilin’, easy-goin’ man, but then he did have somethin’ in his system that fought back and, uh, but that very seldom come out. He was generally pretty good-natured and he was a nice lookin’ man. He weighed about one hundred eighty-five or ninety pounds and was built up nice and so they just called him Pretty Boy, not naturally because he was a sissy or anything like that, but it just got to be a nickname on account of his looks and his actions.

Here’s an old song, though, that uh, is made up of verses that I heard all around over that country. Some of ‘em are tales and legends and stories that the sharecroppers and the farmers and the people that live out, uh, well, kinda like wild hogs on a river bottom. These people knew Pretty Boy Floyd because he, his people, I believe, were farmers also in that part of the country. He lived close to a town called Shawnee and, uh, the story that I heard was that his outlaw career started in the little town of Shawnee, Oklahoma one Saturday afternoon when he come into town and tied his horses up to a hitchin’ rack. He had his wife beside him on the old spring seat of his buckboard wagon and they had made a new ruling since Pretty Boy had been in town the week before, about tyin’ your horses and…automobiles was gettin’ pretty thick down there and so there was a deputy sheriff come out and proceeded to bawl Pretty Boy out for tyin’ his team up there and his language, uh, wasn’t quite suited to the occasion, and uh, he sort of (laughs), well, he…Pretty Boy’s temper just got away from him there when he heard in the presence of his wife, that’s one thing that Oklahoma and Texas and all that country is pretty strict about, is, uh, language that you use in the presence of the women unless you, uh, you know, unless it is personal or friendly or somethin’ like that. But, then, when it comes to a certain tone of voice, you better smile or (laughs), or duck. So, the deputy said it and he didn’t smile and he didn’t duck and Pretty Boy grabbed a log chain out of the wagon that he was in and the deputy went for his gun at the same time. They had quite a fist fight, uh, without fists, and uh, the deputy lost. Pretty Boy took off to the trees and timbers and lived along the river bottom with the farmers for a long time there and uh, in them days, you know, why, there was lots of banks for some strange reason going broke. They was going broke for every kind of reason. If you sneezed out the wrong winder, why, by George, a bank would go broke. If you come in the wrong door, the bank would go broke. If, for the least little excuse the bankers could think of, why, they went broke. So there was several thousand around over the country that went broke and the government stepped in and said, “Boys, now you can’t go broke so fast, you’re gonna have to change tactics, you’re gonna have to make up some new excuses to go broke”. So the bankers said, “Well, uh, okay, we’ll watch it.” So, they thought well, now, if we could just get somebody to rob us, by George, from the inside everything would be hunky-dory. So, when Pretty Boy Floyd was hidin’ out from the officers of the law because of the deputy sheriff fight that he had, why, uh, there come reports from all over the state, three or four hundred miles away that Pretty Boy Floyd and a band had just robbed a bank when about twenty five or thirty farmers knew damn well that he was sittin’ right there, right then.

Track 5 – AFS3413 A

WG: Well, at that time, that got to be a pretty big joke around over Oklahoma, Alan, in fact all over that country. Banks was being robbed by Pretty Boy Floyd, Pretty Boy Floyd, Pretty Boy Floyd here, yonder, everywhere. He was worse than quintuplets, man, he was runnin’ all directions at the same time, had three guns in each hand and a whole bunch more in his pocket, but anyway, there was lots of people knew where he was and what he was doin’, so it got to be quite a joke. And so these farmers hid him out. Down in that country, they always hid him out because they knew that although he might have been a bad man he wasn’t being given a fair chance.

AL: Well, how did he get those thousand-dollar bills Woody?

WG: Well, uh, a little bit later, his, he went his limit again and I guess his temper got the best of him and it is said that he said, they, uh, they are makin’ me a outlaw, they’re gettin’ the money and I am gettin’ the advertisement. He said, I think I will just reverse the deal, he said that. I’m gonna take the cash and let the credit go. So he took out with a six-shooter in each hand. Here’s a little story I believe I’ll sing about it. I want to say, though, that Pretty Boy did get shot down like all outlaws and his character gets shot down some way or the other, by one of their own men or by one of the Judases in the deal or one of the dirty little cowards in the Jesse James songs. Pretty Boy got his and he is laying in his grave right today, but I want to venture to say without stretching the truth, that Pretty Boy Floyd is sung about on more lips and more mouths than and thought better of, in more hearts. He’s all-around more popular than any governor that Oklahoma ever had.