In 1997 at the Mississippi State Penitentiary, elderly convict Willie Long recounts his friends’ life story during their burial. Ray Gibson and Claude Banks, New Yorkers from different worlds, meet at a club called Spanky’s in 1932. Ray, a small-time thief, picks Claude as a mark. They annoy the club’s owner, who threatens Claude. Ray convinces Spanky to allow himself and Claude to pay off their debt via boot-legging. Claude and Ray travel south to buy Mississippi “hooch”. They pay for the booze and enter a local bar, where Ray loses his father’s prized pocketwatch to hustler Winston Hancock in a fixed game of cards. Outside, the town’s sheriff, Warren Pike, kills Hancock and frames Ray and Claude.
Ray and Claude are sent to perform hard labor at an infamous prison camp. Ray and Claude immediately run afoul of the guards, Sergeant Dillard and Hoppin’ Bob, and meet fellow inmates Jangle Leg, who makes a pass at Claude; Willie Long; Biscuit, another homosexual inmate, involved with Jangle Leg; Radio; Goldmouth, a bully who picks a fight with Ray; Cookie, the chef; and Pokerface. Claude’s cousin, an attorney, unsuccessfully appeals his conviction and seduces his girlfriend. With no chance at freedom, Claude and Ray break out, getting as far as Tallahatchie before being captured.