Keanu Reeves plays the title character, a toll booth operator without much of a future. His girlfriend (Judy Greer) tries to suggest that kids might fill that gap for the both of them, but Henry struggles enough with that prospect that he decides to join a November softball game with Eddie Vibes (Fisher Stevens) instead of making a decision. Unfortunately for Henry, Eddie and his two pals aren't taking Henry to a softball game, but a downtown bank, which they rob and hoof it from, leaving Henry, in what turns out to be a stolen car, to take the fall. In prison, Henry meets Max (James Caan), a con man content to live out his years in the joint. Inadvertently, Max puts a simple idea into Henry's head: if you did the time, you might as well have done the crime. A couple of years later, on the outside, Henry decides to put that advice in action.
Good old Keanu Reeves. As an actor, he's always been more about physicality than soulful-eyed emoting, but he finds some good notes to play in a character that has a bit of brightness to him. Although Henry is often a bit of a blank slate, he's not as dour as the roles Reeves usually ends up playing, and he's considerably livened up in the presence of Julie (Vera Farmiga), a local actress dreaming of bigger things. Henry's bank-robbing scheme involves accessing an old tunnel between the playhouse and the bank vault, and as a result, he ends up joining the same play as Julie, Chekhov's The Cherry Orchard. Farmiga is loose and off-beat in a way that's too unique to be reduced to a word like "quirky," and she and Reeves have appealing chemistry. When Julie prompts Henry to act, Reeves is actually pretty good, injecting a bit of life into his usual blank stare.
Reeves also forms a believable friendship with Caan's Max, played by the veteran with a surprisingly warm-hearted decency. Although some of Caan's picks of late have been on the goofy side, his confidence-man bit is no joke, played beautifully in several scenes when Max needs to extract information about the bank and playhouse. As the scope of the job expands, other characters are equally well-integrated: Joe (Danny Hoch), the would-be getaway driver whose weak stomach put Henry in the driver's seat on the big day years previous, or Frank (Bill Duke), the tired security guard who arrested Henry then, but might feel differently today. The charm of Henry's Crime really lies in this group of well-conceived and well-performed characters just sitting around and interacting with each other, an art that sometimes seems to be lost in over-plotted movies.
That said, plot still manages to creep in, and screenwriters David N. White and Sacha Gervasi (the director of Anvil!) can't quite overcome the fact they've written a film with very few places to go. As the big moment draws near, Henry begins to have doubts about leaving Julie, and the film works itself into a corner, slowly but surely taking the characters out of control. Not only is the conclusion the film devises pretty conventional, but it's a definite disappointment following 70 or so minutes of airy, refreshing character material. Ending and all, Henry's Crime is enjoyable, but it could've been more than that, if in the end the emphasis remained on Henry rather than the crime.
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