In the 30s, three men escape from a Mississippi prison. The trio: Everett (George Clooney), Delmar (Tim Blake Nelson), and Pete (John Turturro), embarks on the adventure of a lifetime as they set out to pursue their freedom and return to their homes. With nothing to lose and still in shackles, they make a hasty run for their lives and end up on an incredible journey. However, they must also match wits with the mysterious lawman, Cooley, who is bent on bringing the trio back to the prison.