"Fucking hilarious," murmurs a small-time Buffalo actress to her new suitor when he confesses his armed-robbery plans in Henry's Crime; alas, she has no nose for material. This farrago of indie quirk and classic screwball tropes develops no momentum in either mode, jerking to occasional life in bits of criminal action before collapsing again into sluggishness. A thickened and morose Keanu Reeves is the titular New York Thruway toll collector, whose diffidence and stupidity result in his unwittingly becoming the driver for an asshole former classmate (Fisher Stevens) and his crew on a failed bank heist. Sent to prison as the job's sole arrestee, Henry loses his marriage but gains a guru in a philosophical con-man cellmate (James Caan in a role that Peter Falk would've had a dozen years back) who claims that the failure of all guests of the penal system is "we weren't true to our dreams." Revivified by the concept of successfully breaking into the same bank he was nailed for failing to rob (the "hilarious" plot that never convinces on any level), Henry is soon courting the insecure thespian (Vera Farmiga) who hit him with her car, as she's starring in a production of Chekhov's The Cherry Orchard that's rehearsing in a theater connected by a Depression-era tunnel to the targeted vault across the street.
Trotting out variations on assorted wacky genre standards (a meet-cute accident, an egomaniacal Russian stage director played by Peter Stormare, and Danny Hoch as a nervous felon reliably who pukes under pressure), the scenario labors in a stale haze of recycled shtick, retrospectively giving the criminals-in-the-theater fluff of Woody Allen's Bullets Over Broadway a buffed, masterly stature. Director Malcolm Venville, with an assist from Collateral cinematographer Paul Cameron, unexpectedly gives the alleys and wide streets of downtown Buffalo a blue-gray beauty, but can't overcome the script's leaden missteps, like Reeves's unreadable motivations and bank guard Bill Duke's tragic backstory, or the mismatched energy between Keanu's stolidity and Farmiga's shrill flightiness. The gleam in Caan's eye as the mischievous old pro is the movie's most energetic asset, but when sleazeball Stevens predictably reenters as a third-act complication, it's not remotely plausible that he could intimidate Neo and Sonny Corleone. Even with a hail-Mary soundtrack infusion of sleek songs by Sharon Jones and the Dap-Kings, Henry's Crime is so moribund that you'll wish it stuck with Reeves's unlikely casting as Lopakhin in the Chekhov play as its focus rather than just a cutesy twist.