In 1997 at the Mississippi State Penitentiary, elderly convict Willie Long tells his friends' life story at 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. Ray convinces club-owner Spanky to let him and Claude pay off their debt via boot-legging. Traveling south to buy Mississippi "hooch", they pay for the booze and enter a local bar. Ray loses his father's prized pocketwatch to card hustler Winston Hancock. Outside, sheriff Warren Pike kills Hancock, framing Ray and Claude.