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In the 1870s, Billy Bonney arrives with his mother Catherine and stepfather Henry McCarty in the bleak prairie town of Coffeyville, Kansas, the end of the Galveston railroad line. Henry has moved the family from their home in New York to start a new life as farmers. As Billy, who resents the move, sullenly surveys the muddied rut that serves as the main street in Coffeyville, the family is met by mayor Ben Antrim, who persuades Henry to buy a rundown piece of property on the outskirts of town. Later, at a town meeting, Ben, who owns much of the town and thus stands to prosper by its development, introduces Henry and his family and enthusiastically announces that due to an epidemic in a nearby town, its entire population of fifty may be moving to Coffeyville, thus qualifying it to be a "third-class city," and allowing them to hire a professional lawman. Henry expects Billy to help with the grueling, dirty work needed to transform the hardscrabble land into a prosperous farm, but Billy, who considers himself a city boy, rebels, earning Henry's contempt and abuse. One night, Henry, fed up with Billy's recalcitrance, throws the boy out of the house and threatens to kill him if he comes back. Billy decides to hop a train back East with a bunch of hoboes, but once on board, changes his mind, jumps off and trudges back to town. On the main street, Billy is being heckled by several hooligans when a gunfight erupts in the saloon and spills out onto the street, scattering Billy's tormentors. When one of the men from the saloon falls dead on the street, Goldie Evans, a reprobate who has made the saloon his home, asks Billy to extract the knife protruding from the dead man's body and give it to him. Billy then enters the saloon, where Goldie warns him to be wary of Ben, whose only interest is to profit from the town. Soon after, Ben comes to the saloon and bribes Goldie to send Billy out. Billy reluctantly leaves, but after stealing some bread and eggs from his stepfather's farm, eagerly returns. Billy is met by Berle, Goldie's girl friend, who supports the couple by prostituting herself in a back room of the saloon. After Berle throws Billy out of the saloon, he is approached by the ruffians, who offer him a small amount of money to deliver some tobacco to Goldie. When Billy demands more money from the ruffians, Goldie, impressed by Billy's initiative, lays out his plan to rustle cattle and sell them to the army. Jawbone, the proprietor of the saloon, then offers to let Billy stay the night. Soon after, the town celebrates as the settlers from their neighboring town move to Coffeyville, thus officially boosting it to the rank of a third-class city. One day during a card game at the saloon, Goldie bets his opponent, a buffalo hunter, his entire grubstake. Once the money is put on the table, Goldie pulls out his gun and fires at the buffalo hunter, but when his gun jams and the enraged man charges him, Goldie yells to Billy to pick up the man's gun and shoot. Billy does as he is told, but the gun backfires, knocking Billy off his feet. Berle then attacks the hunter's woman, Lou, with her knife. After Lou slices Berle in the arm, Berle cuts off Lou's ear, sending Lou squealing into the street with the hunter not far behind. Impressed by Billy's tenacity, Goldie offers to teach him to shoot. Berle protests the inclusion of Billy in their group, and when she refuses to have sex with a customer, Goldie hits her until Billy tells him to stop. Goldie then placates Billy by arranging for him to have sex with Berle, and after an exchange of sexual and personal intimacies, Berle affectionately hugs Billy. Soon after, Henry dies, and at the funeral, Billy watches as Ben comforts Catherine. Afterward, Ben informs Billy that he has hired Earl Lovitt, a feared sheriff, to get rid of Goldie, then tries to cajole Billy into taking a reputable job. Later, at a town meeting about banishing Goldie, Ben argues that Goldie is also a member of the town and should be allowed to leave peacefully. Ben then goes to tell Goldie that he must be gone by morning, and that a horse will be waiting for him to ride out of town. Goldie angrily reminds Ben that his parents helped settle Coffeyville, then threatens to destroy the town if forced to leave. Nevertheless, the next morning when Ben comes to the saloon with the horse, Goldie and Berle say goodbye to Jawbone and Billy, after which Goldie mounts the horse as Berle walks beside them on their way out of town. As the townsfolk gawk from the doorways, several snipers open fire on Goldie, wounding him. Furious at the betrayal, Berle runs into the saloon, grabs a rifle and begins shooting at Goldie's assailants, who shoot her down, killing her. Ben tries to restrain Billy, who kicks him in the groin and runs out into the street just as Goldie jumps on the horse and escapes. Later, the morose Billy catches up to Goldie, who shows him a map leading the way to the hideout of Big Jim McDaniels, where they hope to find refuge. Upon reaching the hideout, however, Big Jim and his men threaten them with robbery and sodomy. One of the outlaws is about to molest Goldie when Billy shoots the man in the head, then pummels him with his gun butt. Now full-fledged killers, Billy and Goldie take the outlaws' clothes, guns and horses and ride off.