Damn, it's hard to be a gangster. Particularly in this economy. Don't be fooled. When your wallet's empty, the bad guys are feeling the pinch, too.

Or so we come to learn in Killing Them Softly, the new feature from Andrew Dominik, the long-awaited follow-up to his masterful The Assassination of Jesse James by the Coward Robert Ford. The writer/director is working from a novel by author George V. Higgins here. Higgins also wrote the source material that became the cult 1970s crime film The Friends of Eddie Coyle, a film it'd be a safe bet to say Dominik has seen. His crooks and killers look like throwbacks to that era, as do their cars. Killing Them Softly doesn't go back that far in time, however; Dominik sets the action in 2008, in the weeks leading up to Barack Obama's election. The news is on throughout the movie, and all the underhanded shenanigans on screen are underscored by stump speeches and financial flailing in the real world. As things fall apart in their small 'burg, so too is Wall Street disintegrating.

Brad Pitt leads an ensemble cast as Jackie, a cool-as-ice hitman called in after a couple of low-level robbers knock over a private card game. The gunmen in question are Frankie (Scott McNairy, Argo) and his Australian buddy Russell (Ben Mendelsohn, Animal Kingdom). The two met in jail, and they have been struggling ever since they got out. Russell has a scheme to buy some heroin with money raised selling stolen dogs, but Frankie has a bigger score in mind. The idea to rob the gamblers comes from a two-bit crime boss nicknamed Squirrel (The Sopranos' Vincent Curatola). Though private gambling nights are generally considered off-limits and boosting them would mean certain death for the thieves, Squirrel has found a way to juke the system. A couple of years ago, one of the made men, Markie (Ray Liotta, Goodfellas), had his own card game robbed, rightly guessing that no one would really believe he did it and he'd get away with the loot. Markie's big move is now the stuff of legend, and Squirrel is banking that not only will the other gangsters think Markie was dumb enough to do it a second time, but they won't turn a blind eye at being duped again.

Though the set-up sounds complicated, it really is just the set-up--and just a small sliver of what Killing Them Softly has going on. The fall-out gets even more complicated, as Pitt's Jackie is called in to manage the situation and set things right. It's all about making the gamblers feel safe at play and sending the message that this kind of thing won't be tolerated. Jackie has clandestine meetings with an intermediary (Richard Jenkins, The Cabin in the Woods) who shuttles messages back and forth between the killer and the big bosses. These days, the organization is a long way away from one impulsive hothead being in charge; it's now an indecisive committee. This means wheels grind slow, even as more players get involved and the waters get further and further disturbed.

The parallels between this bunch of crooks and the bunch of crooks in Washington and on Wall Street are pretty obvious, though Dominik is careful not to have anyone point it out. The newsfeed exists as background noise, and excepting one climactic moment where all of this heady material is sent home like a hammer hitting a firing pin, no one ever makes comment on it. They have plenty of other things to comment on, anyway. The best scenes in Killing Them Softly are the long conversations between the various characters. They discuss their crimes and their vice, but they also talk about their dreams and their anxieties. Regardless of their position in the food chain, every outlaw seems to be suffering from the same malaise: this is not the lifestyle they were promised, it's not the vocation they had in mind. No one better exemplifies this than the out-of-town hired gun, New York Mickey, played by Tony Soprano himself, James Gandolfini. Mickey is called in to handle a part of the gig that Jackie would rather not do himself, but he's seen better days. Marital woes, scrapes with the law for minor infractions, too much booze--Mickey is a mess. Gandolfini plays him with false bluster and a sad humor. It's a great part, mostly just a two-scene cameo, but it perfectly illustrates how the myth of gangster life has floundered.

Pitt is an ideal fit for Jackie. The actor is often at his best in roles where he is required to hold back. Jackie is like the last of a dying breed, a professional who takes his job seriously and holds his cards close. His mystery makes him charismatic, even though he's also a little scary. The first time we see him at work, Dominik and director of photography Greig Fraser (Snow White and the Huntsman) shoot the gunplay in slow-motion, turning the murder into an abstract smear of motion and texture. It's both brutal and beautiful, a contradiction Dominik is more than aware of. The violence throughout Killing Them Softly is a mix of visceral ballet work, dark humor, and sickening consequences. We get our thrills and our inappropriate laughs, but we also get shown what we're laughing at, like the guy we're making fun of was standing behind us the whole time and he heard everything we said. The shame of getting caught is linked to the excitement of having done bad.

Killing Them Softly is a skillful balance of pretension and genre, low art made with high craft. Carefully considered dissolves work with an underplayed score (The Grey's Marc Streitenfeld is credited with "piano pieces and musical ambiences"), while music cues to rival even Scorsese both enhance and ironically comment on all the wickedness on display. As the story develops, Dominik simultaneously caters to and defies expectation. Some things pay off the way bets in this kind of story should; in other instances, Dominik ditches the favorite and goes for the long shot. It's those decisions that bring the largest returns, making Killing Them Softly one of 2012's bigger surprises, sneaking in just under the wire as one of the best of the year.

Jamie S. Rich is a novelist and comic book writer. He is best known for his collaborations with Joelle Jones, including the hardboiled crime comic book You Have Killed Me, the challenging romance 12 Reasons Why I Love Her, and the 2007 prose novel Have You Seen the Horizon Lately?, for which Jones did the cover. All three were published by Oni Press. His most recent projects include the futuristic romance A Boy and a Girl with Natalie Nourigat; Archer Coe and the Thousand Natural Shocks, a loopy crime tale drawn by Dan Christensen; and the horror miniseries Madame Frankenstein, a collaboration with Megan Levens. Follow Rich's blog at Confessions123.com.