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Henry's Crime is a 2010 American Romantic Comedy crime film directed by Malcolm Venville and starring Keanu Reeves, Vera Farmiga, and James Caan.

Working the night shift as a toll collector on a lonely stretch of highway in Buffalo, New York, Henry (Reeves) is a man seemingly without ambition, dreams or purpose; a man sleepwalking his way through life. He gets his wake-up call early one morning when he becomes an unwitting participant in an ill-conceived bank heist. Rather than give up the names of the real culprits, Henry takes the fall and goes to jail. There, he meets the irrepressible Max (Caan), a Con Man who's 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. Upon his release one year 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 theatre across the alleyway, he convinces the reluctant Max to file for his long overdue parole - and then recruits his former cellmate to help stage a robbery. Their plan is simple: by infiltrating the theatre and its current production of Chekhov's The Cherry Orchard, the unlikely duo will buy just enough time to dig their way to the adjacent bank vault and drive off with their loot. Unfortunately that plan also includes Henry taking the lead role in the play, where he finds himself slowly falling for the production's mercurial leading lady, Julie (Farminga).

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Henry's Tropes:

  • Bank Robbery: The same bank gets robbed twice. The first is an amateurish smash-and-grab committed by Eddie Vibes and his buddies where the run in, grab the cash and run out holding armfuls of money. Henry, who was unknowingly the getaway driver, gets caught and sent to jail. When he gets out, he decides that as he already done the time, he should do the crime, and plans a far more sophisticated robber involving tunnelling from the theatre next to the bank.
  • The Caper: Released from prison for a crime he didn't commit, an ex-con targets the same bank he was sent away for robbing.
  • The Convenient Store Next Door: Henry discovers a long forgotten bootlegger's tunnel which runs from the bank to a theatre across the alleyway. He and Max plan to infiltrate the theatre and its current production of Chekhov's The Cherry Orchard to enough time to dig their way to the adjacent bank vault.
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  • Desires Prison Life: Max is a Con Man who has grown far too comfortable with the familiarity and security of his "idyllic" life behind bars, to the extent that he deliberately screws up his parole hearings so he will not be released.
  • The Door Slams You: Henry and Max are inspecting the bank wall to work out where the tunnel runs when Julie comes storming out of the theatre and slams Henry with the stage door.
  • Film Felons: Henry discovers a long forgotten bootlegger's tunnel which runs from the bank to a theatre across the alleyway. He and Max plan to infiltrate the theatre and its current production of Chekhov's The Cherry Orchard to enough time to dig their way to the adjacent bank vault.
  • Hard-Work Montage: Used to show Max and Joe clearing out the dirt in the tunnel between the theatre and the bank over the course of rehearsals.
  • Healthcare Motivation: A slightly variation provides the motivation of Frank the bank guard becoming the Inside Man for Henry's Bank Robbery. Frank had worked for the bak for 30 years and he and his wife planned to retire to the south of France. A year before he was due to retire, his wife became ill, and his insurance wouldn't cover the full cost of her treatment. The bank refused to make up the shortfall despite his years of loyal service (and foiling at least one robbery), so Frank was forced to use his retirement savings to pay for her treatment. His wife died anyway, and Frank was left unable to retire as all of his savings were gone. Joining the robbery is his way of both funding his retirement and getting revenge on the bank.
  • Inside Man: Frank, the same bank guard who caught Henry during the original Bank Robbery, spots Henry and Max scoping out the bank and works out what they are planning. He then offers to join them—letting them know when the maximum amount of cash will be in the vault and deactivating the alarms—as a way of both funding his retirement and getting revenge on the bank for refusing to pay for his wife's treatment.
  • Just Got Out of Jail: Released from prison for a crime he didn't commit, an ex-con targets the same bank he was sent away for robbing.
  • Man Bites Man: When Eddie points his gun at Henry, Joe bites him on the wrist; forcing him to drop the gun, but also causing him to fire and hit Henry in the leg.
  • Meet Cute: Henry and Julie meet when Julie runs him down with her car while he is scoping out the bank.
  • Not Used to Freedom: Max is a Con Man who has grown far too comfortable with the familiarity and security of his "idyllic" life behind bars, to the extent that he deliberately screws up his parole hearings so he will not be released.
  • The Old Convict: In prison, Henry's cellmate is 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.
  • Pistol-Whipping: When Eddie double-crosses the crew and tries to steal all the loot, he clouts Max over the back of his neck with his pistol. He underestimates how tough an old man who has spent most of his life in prison can be, however.
  • Secret Underground Passage: Henry discovers there is an old bootlegger's tunnel running from the bank to the theatre across the alley. He plans to reopen the tunnel and use it to rob the bank.
  • Vomit Indiscretionshot: Crime seems to disagree with Joe's stomach. Henry gets suckered into the ill-fated first robbery when he finds Joe throwing up on his lawn, and Eddie talks him into taking Joe's place in the 'baseball game'. When Henry pulls off the second robbery a year later, Joe get so nervous he vomits in the vault. Both instances are shown in all their glory.
  • What Are You in For?: When Henry first becomes Max's cellmate, Max asks him what he is in for. Henry replies "bank robbery" and Max approves; commenting it is a 'clean' crime. When Henry asks Max what he is in for, Max answers "Life".

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