You Can't Win is an American period film based on the 1926 bestselling memoir recounting Jack Black's acceptance into the Yegg Brotherhood and his life on the road and in jail. Jack's philosophy hardened into isolation, distrust, and aggressive, systematic opportunism as his time in jail lengthened and intensified. The resolution of the film is true to Jack's biography - tension between two ways of life, the upperworld and the underworld, challenged Jack's assimilation and forced him, and the audience, to ask, "Can a man change his life?"
