Woody Guthrie and Pretty Boy Floyd never met, but that didn’t keep Oklahoma’s favorite balladeer and bank robber from forging a legacy together. Since it debuted just over 75 years ago, Woody’s “Pretty Boy Floyd” has become one of the most famous outlaw songs in American history. Folk royalty sing it. Fans praise it as […]

A Six-Gun and a Song

by Dale Ingram


Woody Guthrie and Pretty Boy Floyd never met, but that didn’t keep Oklahoma’s favorite balladeer and bank robber from forging a legacy together.

Since it debuted just over 75 years ago, Woody’s “Pretty Boy Floyd” has become one of the most famous outlaw songs in American history. Folk royalty sing it. Fans praise it as a classic tale of rich versus poor. Critics bristle that it romanticizes a killer.

Woody’s tune was borrowed, and the fanciful lyrics exaggerate the benevolence of the “Robin Hood of the Cookson Hills,” but who cares?

“How much of Pretty Boy’s goodness was true and how much [was] myth doesn’t matter much. His life was the stuff of which folklore is made,” Studs Terkel wrote in a 1961 article for Climax magazine.

The song endures, some say, because its message resonates as much in 2015 as it did when Woody recorded it in 1940.

“The song really asks, ‘Who is the criminal?’ That is the basic philosophical question it asks,” said Rachel Jackson, a labor activist who lives in Norman and has arranged for the song to be played at union events. “People are still fighting that same fight. Working Oklahomans are still dependent on the mercy of the rich, and their gigantic fountain pens have gotten a lot bigger.”

It’s not clear when Woody Guthrie first sang “Pretty Boy Floyd.” The margin notes of a handwritten draft dated March 1939 suggest it was intended to be sung on his homespun program on KFVD radio in Los Angeles.

Of the 12-verse song, the first five describe an imaginary scene where Pretty Boy defends his wife’s honor against a rude, vulgar deputy sheriff. The lawman’s gun was no match for Pretty Boy’s swinging log chain, but the episode resulted in Pretty Boy hiding in the Oklahoma timber while “every crime in Oklahoma was added to his name.”

The next five verses, while making no mention of Pretty Boy’s brutal criminal career, builds a résumé of feeding starving farmers, paying off mortgages, and surprising hungry Oklahoma City families with car loads of groceries and a note:

Well, you say I’m an outlaw,

You say that I’ve a thief,

Well here’s a Christmas dinner

For the families on relief.

The final two verses are biting political commentary and some of Woody’s most memorable words:

Now as through this world I ramble,

I see lots of funny men,

Some will rob you with a sixgun,

And some with a fountain pen.

But as through this life you travel,

And as through this life you roam,

You won’t never see an outlaw,

Drive a family from their home.

“ ‘Some people will rob you with a sixgun, others with a fountain pen’ — that was probably the greatest line Woody Guthrie ever wrote,” said Greg Johnson, who organizes the annual Woody Guthrie Tribute Concert, nearly 25 years running, at the Blue Door “listening room” in Oklahoma City. “I think the song may have been forgotten without that one line.”

Mysteries of the Phantom Terror

For a high-profile hoodlum who generated so much scrutiny, Charles Arthur Floyd left a lot of unknowns.

Little of his upbringing in Sequoyah County at the dawn of statehood could have made anyone imagine he would become Public Enemy No. 1, suspected in more than 10 murders and 30 bank robberies. Like his peers, his life revolved around tenant farming, moonshining, and a Baptist church. His brother even became a respected local sheriff.

Some say Charley succumbed to the pressure of having a teenage bride, a baby son, and a hate for hard farming. Others insist he was a heartless bully who loved flashy cars, clothes, and women.

While dapper and fit, there is debate on the source of his famous “Pretty Boy” moniker. Legend has it he was first called “Pretty Boy” by a girlfriend in Kansas City. More credible research suggests the nickname was born in a St. Louis newspaper crime report. Regardless of its origin, the outlaw despised the name.

His other nickname — Robin Hood of the Cookson Hills — was less deserved. There is no evidence Pretty Boy was motivated to rob banks with the intent of giving cash to the poor. Yet there were witnesses to his generosity toward some struggling family members and neighbors. And he reminded the world in a note: “I have robbed no one but the monied men.”

There’s no denying his Houdini-like ability to escape tight spots and manhunts, and those getaway skills helped him earn yet another brand: The Phantom Terror.

He jumped from a moving train in Ohio while on his way to prison. He shot his way to freedom from a Tulsa house, a Bixby farm road, a Stonewall barn, and a Kansas City warehouse. Famed aviator Wiley Post may have been the first to fly solo around the world and soar higher than anyone of his day, but even he failed to track down Pretty Boy from the sky.

Maybe the greatest mystery surrounds Pretty Boy’s suspected role in the Kansas City Massacre, the June 1933 slaughter of four lawmen and the convict in their custody. Pretty Boy denied he was there, and there are respected crime historians who argue both sides. Nonetheless, the resulting dragnet all but forced him into a hiatus.

And when he was killed by a posse in eastern Ohio in October 1934, some claim he was only injured by the first shots and callously “executed” while lying on the ground after a brief interrogation. The truth died along with Floyd that day.

Still, there is poetry to Pretty Boy’s death. He wasn’t shot down in a grimy Chicago alley or a dusty Louisiana back road, but by a posse while fleeing through an autumn Ohio pasture, moments after he ate a last supper served by a widowed woman who welcomed the bedraggled stranger into her farm home.

His life and death were made for tabloid newspapers, detective magazines, crime comic books, Hollywood — and a song.

The Farewell Tour

Glendon Floyd chuckled as he scanned a corner lot in Sallisaw, Oklahoma, where the Sallisaw State Bank once stood.

He recalled that on November 1, 1932, this site was where everyone in town — except the local lawmen, it seemed — knew his 28-year-old Uncle Charley Floyd was planning a morning robbery.

It was a comical and ominous scene. Pretty Boy smiled and greeted old friends, yet cradled a submachine gun and kidnapped a cashier to help the getaway. His gang made off with $2,530.

For Glendon, the empty lot was a stop on a miniature Pretty Boy hometown history tour that he offered to those who passed his informal test of kindness and interest. Born on July 4, 1924, Glendon was a military veteran and businessman who in retirement wanted to help shape the outlaw’s legacy.

Glendon said he was enraged by those who portrayed Pretty Boy as one who killed for thrills. He said Pretty Boy never fired a weapon during a bank robbery. He said his uncle killed four men, but only in kill-or-be-killed battles.

Glendon denied his uncle was a Robin Hood figure, but cast him instead as an ever-smiling personal “hero” who shared loot with the family.

“I don’t glorify my uncle, but he helped feed us… with stolen money,” Glendon said.

On a September day in 2009, Glendon drove me by the former train depot where Pretty Boy’s body arrived in a pine casket. He strolled through the cemetery where he joined up to 40,000 for his uncle’s funeral. Glendon grimaced when he noticed more chunks of the “Charles Arthur Floyd” tombstone had been chipped away by souvenir seekers.

I asked Glendon if he liked the song Woody Guthrie had written about his uncle. “I hate it,” he replied.

I reminded him that the ballad emphasized his own themes about Pretty Boy: his generosity, his loyalty to family, and how he was unjustly accused of many crimes.

“Woody Guthrie was nothing but a goddamn communist. I hate it,” Glendon said.

Near sundown, the tour ended. The widower confessed he was lonely. He encouraged me to return soon. He slapped his chest and said he suspected his weak heart would limit his days of telling stories about Pretty Boy.

Four weeks later, Glendon Floyd died.

More Jesus Christ than Jesse James

With “Pretty Boy Floyd,” Woody knew he had something special. His songs about Jesse James, Belle Starr, and Billy the Kid are almost novelty songs about bandits from another era. But Pretty Boy was as contemporary as the suffering Okies who accused the bankers of exiling them to the migrant camps of California. “Pretty Boy Floyd” was a closer cousin to his “Jesus Christ,” “I Ain’t Got No Home,” and other songs that describe injustices to the outcast.

“I have visited the Oakie camps a time or two…” Woody later wrote. “And they just dam near tore down a perfectly good govt auditorium when I sung about Pretty Boy or Tom Joad.”

“Pretty Boy Floyd” was one of the first songs Woody recorded; in March 1940, it was among 29 tunes he sang at age 28 for folklorist Alan Lomax for what became known as the Library of Congress sessions in Washington, D.C.

“I often venture to say — without stretching the truth — that ‘Pretty Boy Floyd’ is sung about on more lips and more mouths, and thought better of in more hearts and all around more popular than any governor Oklahoma ever had,” Woody told Lomax.

Woody knew his own hard travelin’ authenticity was one of his greatest gifts, and he reminded listeners that he and the outlaw were all but neighbors in the eastern Oklahoma hills. “(Pretty Boy) come from about 17 miles from where I was born and raised, and I know people all through this section of the country, and he knows people all through my section of the country,” Woody said.

That same year, “Pretty Boy Floyd” was among 13 songs Woody recorded for his first commercial album; although it was cut when the originalDust Bowl Ballads was released, it often reappeared on the folk singer’s live playlist and songbooks.

In time, Woody passed the torch.

Bob Dylan, Pete Seeger, Joan Baez, Ramblin’ Jack Elliott, Paul Simon, The Byrds, and Rosanne Cash joined the list of those who introduced “Pretty Boy Floyd” to new audiences in new decades. “Pretty Boy Floyd” is a standard at folk music gatherings, including the Woody Guthrie Folk Festival in Okemah.

The influence of the song has extended beyond folk-singing circles. Tulsa author Michael Wallis said Dylan’s recording of the song inspired him to write his landmark Pretty Boy: The Life and Times of Charles Arthur Floyd (St. Martin’s Press, 1991), the first comprehensive biography of the outlaw.

Of course, it is not a universally beloved song. Ron Owens, a former Oklahoma City police officer and author of Oklahoma Heroes: A Tribute to Fallen Law Enforcement Officers, said many in law enforcement bristle when criminals are glorified, but others shrug it off. Pretty Boy simply joined a long line of “social bandits” who are celebrated in songs and stories by oppressed people, he said.

“You resent it to a certain degree but you come to understand it. A career in law enforcement gives you good insight on human behavior,” Owens said. “We (law officers) understand the psychology, the mythology around all these outlaws. These are very bad people, killers, and we all know that. But people elevate them because they see that someone has the courage to do things they wish they had the balls to do themselves.”

Woody may not have known the song would survive to a new century, but he knew it was timeless. Woody wrote:

I sing religious songs. I sing union songs. I sing all kinds of songs about people that are supposed to be mean, or vulgar, low-down, no money, no good, and I sing songs that tell who the racketeers are and how they rob you and how they work you and how they would like to keep you as their slave… And I sing the songs about robbers and about outlaws and people that try to take it from the rich and give it to the poor. I sing songs that tell you just why you can’t help the people that are poor just by grabbing a club or a knife or a gun and going out to be an outlaw. I sing songs about the outlaws that the people loved and the ones that the people hated. I sing any song that was made up by the people that tells a little story, a little part of our big history of this country, yes, or that tells a part of the history of the world.

Originally published in This Land, Vol. 6, Issue 6, March 1, 2015.