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A semi-fictionalized version of John Resko's incarceration is presented. John (Ben Gazzara) is on death row at Sing Sing for murder. In December 1930, he killed a toy store shopkeeper (Arthur Malet) over a teddy bear he wanted to get as a Christmas present for his two-year-old daughter, Cathy, but for which he could not pay. Twenty minutes before John's scheduled execution, he is given a reprieve, his sentence commuted to life, and he transferred to Dannemora. He initially has a difficult time adjusting to life at Dannemora, from the uncaring direction of the prison administration including they not dealing with the issue of bed bugs, to altercations with fellow prisoners who seem to want their two pounds of literal and figurative flesh from John, to news that he receives from the outside about goings-on within his family. However, he does eventually befriend many of his fellow prisoners, especially Nick (Timothy Carey), Iggy (Ray Walston) and Wino (Sammy Davis Jr.). John dreams of escaping from Dannemora, so that he can be at least an economically generating father for Cathy (Susan Silo), even if she may not want to resume a life with him. But one of the principals at the prison may have a way to get prisoners like John out of the system, by giving them creative outlets to show parole boards what is in their innermost thoughts. He wants to nurture what seems to be John's artistic abilities. Although John initially balks at the idea of art as an outlet, he does eventually get a passion for it, which leads to an outcome not expected by either the principal or John.