Charles Arthur Floyd was born on February 3, 1904, in Adairsville, Georgia. In 1911, his family relocated to Akins, Oklahoma, seeking better opportunities. Growing up in a poor farming family, Floyd experienced the hardships of rural life during the early 20th century. At the age of 18, he was arrested for stealing $3.50 from a local post office, marking his first encounter with the law.

In 1925, Floyd was arrested for a payroll robbery in St. Louis, Missouri, and sentenced to five years in prison. He served three and a half years before being paroled. Upon release, he gravitated towards the criminal underworld of Kansas City, Missouri, engaging in various illegal activities. It was during this period that he acquired the nickname "Pretty Boy," a moniker he reportedly despised.

Between 1929 and 1934, Floyd embarked on a notorious crime spree across the American Midwest. He was involved in numerous bank robberies, with estimates suggesting he participated in up to 30 heists. Floyd was known for his use of firearms, particularly the Thompson submachine gun, and for his ability to evade capture.

One of the most infamous incidents associated with Floyd was the Kansas City Massacre on June 17, 1933, where four law enforcement officers and a prisoner were killed during an attempted escape. While the FBI implicated Floyd in the massacre, his involvement remains a subject of debate among historians.

Floyd's actions during the Great Depression earned him a reputation as a Robin Hood figure. Reports suggest that during bank robberies, he would destroy mortgage documents, effectively freeing individuals from their debts. This, combined with his generosity towards the poor, garnered him public support, particularly in Oklahoma, where he was dubbed the "Robin Hood of the Cookson Hills."

On October 22, 1934, Floyd was tracked down by FBI agents and local law enforcement near East Liverpool, Ohio. After a brief chase and shootout in a cornfield, Floyd was shot and killed. His alleged last words were, "I'm done for; you've hit me twice."

Floyd's funeral was attended by an estimated 20,000 people, reflecting his status as a folk hero. His life and exploits have been immortalized in songs, such as Woody Guthrie's "Pretty Boy Floyd," and in various books and films. Despite his criminal activities, Floyd remains a symbol of resistance against economic oppression for many.