Just as his Ocean’s 11 co-star George Clooney delighted critics but baffled and annoyed mainstream audiences with Solaris and The American, Brad Pitt seems intent at this stage in his career to make dark, weird movies that only appeal to an extremely small segment of the population.

First came The Assassination of Jesse James, a long, slow, difficult art film that bombed at the box office but is routinely cited as one of the best movies of the 2000s. Then came Palm d’Or winner and critical favourite Tree of Life, a film that prompted some theatres to post their refund policy on the box office window. And now comes Killing Them Softly, a dark, gritty, talky, low budget crime thriller full of deeply unpleasant characters who do deeply unpleasant things. It’s one of the best movies of the year, but most people are going to hate it.

The opening credit sequence alone is worth the price of admission.

In slow-motion, we see a man walking through a dark tunnel. Then the screen abruptly goes black and we hear a fragment of one of Obama’s 2008 campaign speeches. The speech is cut off mid-sentence, then it’s back to the man in the tunnel. Director Andrew Dominik keeps alternating back and forth between the man in tunnel and Obama, always cutting Obama off at inopportune moments. After a couple of repetitions, the effect becomes deeply disconcerting. Needless to say, this is an extremely strange way to begin a movie, especially a gritty gangster movie set in post-Katrina New Orleans that doesn’t have anything to do with the race for the White House.

It isn’t the last appearance Obama makes either. Throughout the movie, we hear snippets of Obama’s speeches (and some of Bush’s too) on TV’s in the background or on car radios. The reason for this soon becomes apparent—Wall Street isn’t the only institution that faced a crisis of confidence in 2008; the world of organized crime faced a similar problem.

In the first scene, we’re introduced to three sleazy lowlifes—a small-time crime boss known as the Squirrel (Vincent Curatola), a squeaky-voiced ex-con (Scoot McNairy), and an Australian heroin addict (Ben Mendelsohn). They’ll turn out to be the most likable characters in the movie, and all of them are extremely unlikable.

The boss tells the two underlings about a card game that he wants them to rob. Normally, robbing a card game would be a death sentence, but this is a special occasion. It turns out that the guy who runs the card game, Markie (Ray Liotta) previously robbed one of his own card games, then drunkenly confessed to it a few months later. If one of his games is hit again, everyone will assume that Markie was the one behind it. The two proceed to carry out the robbery, which is filmed in long, uninterrupted shots and reaches a level of tension that becomes unbearable.

The rest of the movie focuses on Jackie Coogan (Brad Pitt), a hitman hired to take care of the situation. Luckily for him, the Australian heroin addicted boasted about the robbery, so finding the culprits isn’t a problem. But carrying out the hits does present a few challenges. First of all, he knows the Squirrel personally, and as he explains to the anonymous driver (Richard Jenkins) who serves as a middleman, he doesn’t like to kill personal acquaintances since “emotions get in the way” and “it gets messy.” His solution is to outsource the hit to another hitman, Mickey (James Gandolfini).

This leads to one of the longest and most seemingly pointless sequences ever included in a supposedly mainstream film. When Mickey arrives in town, the first thing he does is get drunk and hire hookers. After a 15-minute-long conversation in a rundown motel room (during which Mickey threatens to beat up a hooker at regular, 2 minute intervals), Coogan realizes that Mickey’s in no condition to carry out the hit, so he sends him back home and decides to do the hit himself.

Another problem that Coogan faces is that he has to kill Markie. Markie had nothing to do with the robbery, but everyone on the street thinks that he did, and if he isn’t killed, the credibility of the organization will suffer. So that’s four hits that Coogan has to carry out. It’s difficult to care whether or not his mission is a success since his targets are terrible people and he’s even worse than they are, but nevertheless the final stretch of the film reaches a level of tension that becomes agonizing. (Warning: Like his fellow Australian John Hillcoat (Lawless), Andrew Dominik doesn’t flinch from the violence, and so in this section we have to endure the spectacle of Brad Pitt shooting people in the head five times at point blank range).

All of this climaxes in one of the most cynical and exciting monologues of recent memory. During a meeting at a bar with the Richard Jenkins character  (which just happens to coincide with Obama’s victory speech), Coogan goes to the washroom and finds the contents of the suitcase waiting for him there not to his liking. When he gets back, Coogan delivers a scathing rejoinder to Obama’s optimistic message. The idea that America is “one people” is preposterous; you can’t depend on anyone, and it’s every man for himself. (Suddenly, that seemingly pointless subplot with James Gandolfini starts to make sense). “America isn’t a country, it’s just a business,” he says. “Now f***ing pay me.”

Some critics have complained that the movie delivers its political message with the subtlety of a sledgehammer, yet few seem to agree on what exactly that political message is. Does the movie endorse Coogan’s point of view? Is it anti-Obama or pro-Obama? Is it a crude anti-capitalist screed, or a really weird, violent lecture on the importance of self-reliance? After just one viewing, it’s hard to say. But what is clear after just one viewing is that Killing Them Softly is a stylish, riveting piece of work that—as unpleasant and hard to watch as it is in places—has all the markings of a contemporary classic.