the story: A hitman explains the mechanics of business.
what it's all about: Over the course of only three films, Andrew Dominik has built a strong legacy. Chopper is an Australian crime drama about a real-life, larger-than-life figure; it gave Eric Bana his first standout performance. The Assassination of Jesse James by the Coward Robert Ford is an elegiac character study about the eponymous event; regardless of the merits of Jesse James himself, Dominik still views it as a tragedy. Killing Them Softly is his first wholly fictional creation (based on a book called Coogan's Trade, by George V. Higgins), and it's a meditation on a whole system. By the end of the film, Brad Pitt is stating "America is...just a business." You will either understand what he's talking about by then, or you won't understand the movie at all.
Killing Them Softly is essentially a mob movie. It's hardly the first mob movie, but it might just be the first one without any glamor attached to it. From Jimmy Cagney to Marlon Brando to Ray Liotta, Hollywood movies have tended to glorify mobsters, or at least held them to be inherently fascinating. Liotta's Goodfellas took it to another level entirely; he's so gleeful and unrepentant about his mobster life he sees anything else as a punishment. Maybe as viewers we're supposed to see the irony of it, but Martin Scorsese has spent so much time guiding us along from Liotta's perspective, it's hard to see it that way. Later, mobsters migrated to television, where James Gandolfini ruled The Sopranos with a iron fist; the final scene of the series famously ends without the viewer knowing whether he ever faces justice; this isn't just ambiguity, it's an open invitation to once and for all root for him.
So to see Gandolfini in Killing Them Softly, indisputably as a ruthless, bad guy mobster, is to finally close a chapter in a very long book. None of Dominik's movies have been massive successes, and that's an understatement. For the vast majority of viewers they don't even exist! Assassination has garnered a cult following over the years, but Killing remains invisible. It's a shame. Part of the reason is no doubt because the movie greets Barack Obama's 2008 election as US president with cynicism; this is considered a sin among the minds most likely to care what a movie has to say about something. The whole movie is about the election; it's as much a framing narrative as Brad Pitt's conversations with Richard Jenkins. When Pitt concludes, in the final dialogue of the movie, that American is a business, Obama's election is on a TV screen in the background.
The whole point of the plot is how relationships affect your fate. Two small-time robbers, including one played by Ben Mendelsohn, are actually the characters we meet first in the movie, and so our sympathies are with them for most of the movie. We see how they think, and how they attempt to outthink the system, and how they fail even when it seems they don't. Pitt and Jenkins discuss their predicament; Pitt is hired to take care of it, but he tries to get out of it, because for him, "killing them softly" means killing at a distance. He doesn't like to get involved unless he has to. Pitt's acquaintance in Gandolfini, meanwhile, reveals how ugly matters really are, and everything he tries not to be, even though he ultimately can't avoid it. It's Jenkins who can pretend otherwise, but only because he's basically at the level of the mob Hollywood usually depicts, the one where nothing really seems to be real, just leaving the gun, taking the cannoli.
Pitt reaches his conclusion because he's tried reconciling things, and it hasn't worked; he still ends up having to become personally involved, and Jenkins tries to pay him less than he's owed, because for Jenkins it's just business, and business usually will try to pay less. But Pitt understands that what business means is having to take control, because no one else is going to look after you. It's not how the business functions that matters, and it's not the outcome that matters, either. It's taking control of your fate. Liotta, in this movie, loses control of his fate. He doesn't realize how badly he screwed himself, just as Gandolfini, for all his bluster, doesn't, or Mendelsohn. It's Pitt who does, because he's ruthless in that business sense, whatever it takes to get ahead.
Anyway, it's fascinating commentary.