In 1935, murderer Mattie Appleyard (James Stewart), bank robber Lee Cottrill (Strother Martin), and young Johnny Jesus (Kurt Russell) are released from the West Virginia State Penitentiary, located in the fictional town of Glory. Appleyard is issued a check for $25,452.32 for his 40 years of prison work, an enormous amount in the Great Depression.
All three men are escorted by prison Captain “Doc” Council (George Kennedy) to the train station. However once on the train, Appleyard realizes that his check is only redeemable in person at the local bank in Glory. Council plots with banker Homer Grindstaff (David Huddleston) to ensure the check is never cashed. He and his accomplices, Steve Mystic (Mike Kellin) and Junior Kilfong (Morgan Paull), travel to another stop down the line in order to kill Appleyard. Informed of the plot by guilt-ridden conductor Willis Hubbard (Robert Donner), the three former prisoners thwart the plan. Kilfong ends up shooting mining supply salesman Roy K. Sizemore (William Windom). Council kills the wounded Sizemore and places the blame on Appleyard, who escapes with Sizemore’s supply of dynamite.
The next day, Council goes to the bank to update Grindstaff. As they talk, Appleyard walks in with some of the dynamite strapped to his chest and the remainder in a suitcase. Appleyard threatens to blow them all up “and half this city block” if the banker does not cash his check. Grindstaff reluctantly complies.
Appleyard and his friends, who followed him back to Glory, split up, planning to meet again later. While waiting at the rendezvous, Cottrill is talked into boarding a houseboat owned by a down-on-her-luck prostitute named Cleo (Anne Baxter) for a drink of whiskey. Also aboard is Chanty (Katherine Cannon), a sixteen-year-old whom Cleo has taken in, hoping to sell her virginity for $100.
Appleyard and Johnny show up, only to be tracked down by Council and his bloodhound. The three friends get away in a skiff, leaving behind the suitcase of dynamite. Johnny is worried about what Council will do to Chanty, so they turn around and go back after Council leaves.
Before leaving, Council has told Cleo about Appleyard’s money. At gunpoint, Appleyard gives her the suitcase that she believes contains the money in exchange for Chanty. After they leave, Cleo tries to shoot the locked suitcase open and blows herself up.
The fugitives are later trapped on a boxcar by Council. The train is a “fools’ parade” as described by Appleyard, going nowhere beyond the local train yard. Luckily for them, guilt-ridden train conductor Willis Hubbard returns and helps them escape. However, he is too afraid of Council to tell the police what he knows.
Council, Mystic, and Kilfong track them to an abandoned house. Council decides he does not want to share the loot, so he kills his two confederates. He then shoots a window out, wounding Appleyard. Johnny throws a stick of dynamite at Council, only to have Council’s bloodhound fetch it back. Appleyard hastily throws it out the window, killing Council.
The men are arrested and Appleyard’s money confiscated, but Hubbard confesses the truth, and Grindstaff is arrested. Appleyard and his friends are exonerated, and Appleyard is allowed to cash his check.