Working the night shift as a toll collector on a lonely stretch of highway in Buffalo, New York, Henry is a man seemingly without ambition, dreams or purpose; a man sleepwalking his way through life. His wife Debbie is not happy with the situation.
One morning Eddie, a friend, drops by to ask Henry to play in a baseball game, as one of the others is ill, and Henry agrees to. As they drive to the game in Henry's car, Eddie asks Henry to stop at an ATM. But Eddie, and two acquaintances also in the car, instead rob the Buffalo Savings Bank, and Henry is arrested as an accomplice.
Rather than give up the names of the real culprits, Henry takes the fall and goes to jail. There he is celled with the irrepressible Max, a con man who has grown far too comfortable with the familiarity and security of his "idyllic" life behind bars, but one who also helps plant an idea in Henry's mind which will change his life forever: for a man to find his purpose, he must first have a dream. Debbie decides to divorce him, and she marries Joe, one of the acquaintances.
Upon his release eighteen months later, Henry finds his purpose. Having done the time, he decides he may as well do the crime. Discovering a long forgotten bootlegger's tunnel which runs from the very same bank to a theater across the alleyway, he convinces the reluctant Max to file for his long overdue parole â to help stage a robbery of the bank.
Max encourages Henry to become an actor in the theater's current production of The Cherry Orchard by Chekhov, to assist Max, "volunteering" to work in the theater, in getting access to the tunnel. Meanwhile, Henry finds himself falling for the production's mercurial leading lady, Julie.
Debbie's husband Joe is recruited to help clearing the tunnel of mud; he informs Eddie, who insists in participating too. Frank, a guard at the bank forced into retirement, helps by informing the robbers when there is a lot of money in the vault. During the actual robbery, Eddie uses a gun to try to take all the money himself, but is overpowered by Max and is left behind in the vault. As the three make their escape, Henry demands Joe stop the car. Henry wishes Max well, and he then returns to Julie.

Question: What does Henry convince Max to do? 
Answer: File for parole. 
Alternative answer: file for parole