Henry (Reeves) is a laid-back toll-booth worker in Buffalo, New York, under pressure to have a baby with wife Greer. He gets out of the conversation when shady pals show up for a “softball game” at 9:00 in the morning. Turns out the guys are robbing the local bank and Henry’s the getaway driver, a fact he only realizes after an older guard (Duke) pulls a gun on him. Henry goes to jail and bonds with Max (Caan), an old coot who enjoys being in prison so much, he’s sabotaged every chance he’s had to get out.
Once Henry emerges, his “normal” life has been upended and he finds himself back at the bank, where he’s promptly run over by Julie (Farmiga), a mercurial actress angling to get a grasp on Chekhov’s play The Cherry Orchard. Wouldn’t you know it; the theater is right next to the bank. And during the prohibition era, a bootlegging tunnel connected the two buildings. Could it still be there? Henry takes Max’s advice: since he’s already done the time, he might as well do the crime.
Screenwriters Gervasi and White have clearly read their share of Elmore Leonard, what with scrappy reluctant criminal types rubbing up against average folks. In particular, Out of Sight (1998) comes to mind with its doomed romance, ticking-clock robbery and groovy 70s-inspired score. But Henry is no Jack Foley (George Clooney), and as played by Keanu Reeves, he’s even more of a blank slate.
Don’t get me wrong, Reeves is pretty good, especially in an extended subplot about what a “natural actor” he is (he ends up taking a role in the Chekhov play as a means to gain access to the tunnel). But since we never really know what drives him, it’s hard to invest. Farmiga does what she can but her fierce performance gives way to sudden bursts of unconvincing tears that not only undermine her character but smack of on-set experimenting that made it into the film. Caan is perfect, soft-spoken and tentative about leaving prison on the one hand, fierce and organized on the other. Duke steals the movie as the bank’s longtime security guard.
The main problem is that Henry’s Crime never really finds its footing. It wants to be a whimsical crime caper, a whirlwind love story and an indictment of pretentious American theater, coming up short on all fronts. (Moving Pictures)
— DENNIS WILLIS