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At a reception following his wedding, Oklahoma farmer Charles Floyd demands an apology from Jack Dowler for insulting his bride, Ruby; Dowler's references to his previous sexual relations with Ruby force Charles to beat an apology out of the intruder. Dowler swears revenge for his public humiliation, and that night he tries to ambush Charles but accidentally kills his rival's father. When Charles goes to Dowler's farm the next morning to elicit a confession, they fight and Dowler is killed. Consequently, Charles is convicted of manslaughter and sent to prison. Four years later he escapes and seeks refuge in a Kansas City brothel run by Beryl, where Betty, one of the prostitutes, is attracted to him. Her affection infuriates Beryl's brother Wallace, who is in love with Betty, and in retaliation, he starts referring to Charles as "Pretty Boy," a nickname that gains national acceptance when Charles joins Ned Short's gang of bank robbers. After several bank holdups, Pretty Boy is captured, but he kills a guard and escapes from the train taking him to jail. He returns to Oklahoma for a brief reunion with Ruby, but even though they are still in love, she realizes that she cannot live the kind of life her husband must now live. "Preacher," a local drunkard, accompanies Pretty Boy back to Beryl's, where they join Betty and Ned Short's gang in a widely publicized crime spree. Short and Preacher are killed in a police stakeout, however, and Pretty Boy and Betty escape to a shack near his old home. After a last goodbye with Ruby, the gang's two survivors rob Pretty Boy's hometown bank. Betty escapes, but Pretty Boy is trapped in a ranch house and dies in a hail of bullets.