Scoot McNairy as Frankie (The Weinstein Company)

It’s telling that the climax for this enjoyable if occasionally overreaching gangster film involves not a shootout but a conversation. As Obama’s 2008 election speech plays in the background, cynical hit man Jackie Cogan loses his cool at all the hope ‘n change coming from the TV set. “America’s not a country,” he snarls. “It’s a business.”

Think of it as de Tocqueville by way of Tarantino. Set in the run-up to the 2008 elections and largely in urban Rustbelt squalor, it attempts to use the heist of a small-time underground poker match as a commentary on the soul of the country that midwifed the recent financial apocalypse.

The low-life slice-of-life drama has Cogan (Brad Pitt, reuniting with writer/director Andrew Dominik from The Assassination of Jesse James) traveling to an unnamed post-industrial town to clean up the mess made by a pair of two-bit crooks, Russell (Ben Mendelsohn) and Frankie (Scoot McNairy), who robbed the illegal poker game. But Cogan has a past with Squirrel (Vincent Curatola), the owner of a dry cleaning business who actually masterminded the stick-up, so he calls in someone to do the deed for him cleanly with no emotional ties to the victims: pitch-hitter Mickey the Killer from New Jersey, a garrulous, chubby midlife crisis in motion played by James Gandolfini.

At its best, the movie’s like a cross between one of those great, matter-of-fact 1970s crime flicks (not surprising in that it’s based on a book written by The Friends of Eddie Coyle scribe George V. Higgins) and a Cohen Brothers film, even sharing one of the Cohens’ regulars, Richard Jenkins. (He plays Cogan’s handler, a frustrated, bureaucratic middle-manager type). But the influence tilts to the Cohens, and you sense Dominik is inspired by the same philosophy that guided them to make that beloved scene in Fargo, where Frances McDormand has a seemingly irrelevant barroom encounter with an old high school admirer. Character is allowed to grow, with Dominik generously lavishing much of the film’s brisk 97-minute running time on personal stories of the hoods. Most scenes—a sit-down between two veteran killers at a bar—serve to advance personalities, not the tale.

Mendelsohn, an Australian actor little known in the States, does especially well in these bits as an appealingly spacey junkie-cum-dognapper. McNairy, in his best Ratso Rizzo impersonation, is maybe too middle-class and indie-rock to be convincing as a smalltime hood, but it’s nice to see Gandolfini in what must be his best role since The Sopranos. (Pitt merely has to wear unbuttoned shirts and look cool; not, one assumes, a problem for him.)

This focus on personality over plot leads to one of the most idiosyncratic scripts in recent memory, giving lovers of the outré a mother lode for quote mining. I don’t want to spoil too many lines, but there are some beautifully off-the-wall ones, such as when Gandolfini’s whore-loving killer Mickey tells Pitt, “When you want ass, there’s nothing in the world like a young Jewish girl who’s hooking.” (Um, I’ll take your word for it?)

It’s a shame then that the grander aims of the film consistently falter. Dominik’s attempt to give his petty crime tale some political heft never gets beyond glimpses of decayed neighborhoods in establishing shots and some audio clips of 2008 talk radio or campaign speeches. The cynicism is shocking but empty. (Try to find anything but adolescent posturing behind the “America’s a business” nonsense.) If anything, these moments feel like a pretentious interruption to what is otherwise a bloody good ride.