Uploaded December 2023 | Updated September 2026, 3 weeks ago
“If you'll gather round me, children,
A story I will tell
'Bout Pretty Boy Floyd, an outlaw,
Oklahoma knew him well.
…
Yes, he took to the trees and timber
To live a life of shame;
Every crime in Oklahoma
Was added to his name.
But many a starvin' 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.”
Those words come from “The Ballad of Pretty Boy Floyd,” a song by American folk icon Woody Guthrie. And it perfectly encapsulates the complex and controversial legacy left behind by one of America’s most notorious outlaws. Pretty Boy Floyd was a robber and a killer, no doubt about that. He became the country’s new “Public Enemy #1” after the death of John Dillinger.
And yet, many people remember him as the so-called “Robin Hood of the Cookson Hills” for his generosity towards the needy and, most famously, for allegedly burning mortgage documents whenever he robbed a bank to get people out of debt. But was this reputation deserved or did Floyd simply benefit from good post-mortem PR?
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Further Reading:
Jeffery S. King - The Life and Death of Pretty Boy Floyd
Crime Library
fbi.gov/history/famous-cases/kansas-city-massacre-pretty-boy-floyd
carnegie.lib.oh.us/Floyd
history.com/this-day-in-history/pretty-boy-floyd-is-killed-by-the-fbi
odmp.org/officer/2512-special-agent-curtis-c-burks
findagrave.com/memorial/29508242/ervin-andrew-kelley
biography.com/crime/charles-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.
…
Yes, he took to the trees and timber
To live a life of shame;
Every crime in Oklahoma
Was added to his name.
But many a starvin' 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.”
Those words come from “The Ballad of Pretty Boy Floyd,” a song by American folk icon Woody Guthrie. And it perfectly encapsulates the complex and controversial legacy left behind by one of America’s most notorious outlaws. Pretty Boy Floyd was a robber and a killer, no doubt about that. He became the country’s new “Public Enemy #1” after the death of John Dillinger.
And yet, many people remember him as the so-called “Robin Hood of the Cookson Hills” for his generosity towards the needy and, most famously, for allegedly burning mortgage documents whenever he robbed a bank to get people out of debt. But was this reputation deserved or did Floyd simply benefit from good post-mortem PR?
→ Subscribe for new videos at least twice a week!
youtube.com/c/biographics?sub_confirmation=1
Love content? Check out our other YouTube Channels:
Geographics: youtube.com/channel/UCHKRfxkMTqiiv4pF99qGKIw
TopTenz: youtube.com/user/toptenznet
Karl's Socials:
Fact Fiend: youtube.com @FactFiend
Wiki Weekends: youtube.com @wikiweekends
Untitled Side Channel: youtube.com @untitledsidechannel
Twitter: twitter.com/KarlSmallwood
Further Reading:
Jeffery S. King - The Life and Death of Pretty Boy Floyd
Crime Library
fbi.gov/history/famous-cases/kansas-city-massacre-pretty-boy-floyd
carnegie.lib.oh.us/Floyd
history.com/this-day-in-history/pretty-boy-floyd-is-killed-by-the-fbi
odmp.org/officer/2512-special-agent-curtis-c-burks
findagrave.com/memorial/29508242/ervin-andrew-kelley
biography.com/crime/charles-pretty-boy-floyd
