Brad Pitt plays Jackie Cogan, a hit man who prefers to kill people “softly,” meaning with as little fuss and muss as possible.   But because he is a hit man, he is constantly surrounded by messes that he is asked to clean up.  Two dumb crooks (Scoot McNairy and Ben Mendelsohn) are recruited by a dry cleaner to rob an illegal poker game run by Markie Trattman (Ray Liotta).  Since it is generally understood that Markie had arranged the robbery of one of his own games in the past, the dry cleaner figures that he will be assumed to be behind this one, too, so no one will come after them.  In other words, a mess.

Time for Cogan.  But Cogan knows the dry cleaner, and he prefers to kill people he doesn’t know.  Not because he has scruples — it’s just because the ones who know him know why he is there and they get all upset and start crying and begging.  And that is messy.  So Cogan brings in some help from out of town, another hit man named Mickey (James Gandolfini).  They’ve worked together well in the past, but since the last time Cogan saw him, Mickey has started to unravel.  More mess.

Prosecutor-turned novelist George V. Higgins had a rich appreciation for his underworld characters and the complexity of their compromised and thuggish connections. His dialog-driven books are filled with tough talk that feels authentic and poetic at the same time.  This film is based on a book published in 1974, set in Higgin’s lifelong home town of Boston.  Here it is updated to the summer of 2008 and relocated to Louisiana, where the dialog is counterposed with television broadcasts of a panicked George W. Bush explaining the financial meltdown following the collapse of the subprime market and candidate Barack Obama is making speeches filled with optimism and promise.  The violent scenes, with slo-mo spurts of blood, are counterposed with cheery pop songs, Petula Clark singing “Windmills of Your Mind” and Cliff “Jiminy Cricket” Edwards warbling “Paper Moon.”

(Note: “Windmills of Your Mind” was the theme song of the original “Thomas Crown Affair,” with Steve McQueen as a millionaire businessman with a sideline as a criminal mastermind.) One of those moments would be plenty.  We get it, we get it, the real crooks are on Wall Street and in Washington.  Balletic blood spatters juxtaposed with songs are ironic.  Or something like that.

Choice moments — Gandofini’s monologues, the conversations between Cogan and his bureaucratic contact known just as “The Driver” (Richard Jenkins), and juicy talk cannot make up for the feeling that this is Mamet Lite, and just the kind of messiness Cogan is wise enough to resist.

Parents should know that this story concerns criminals and thugs including drug deals and hit-men.  It includes very graphic violence with disturbing images, dead bodies, constant very strong language, explicit and crude sexual references,  a prostitute, smoking, drinking, and heroin.

Family discussion:  What is the point of the news broadcasts about the financial meltdown?  How does this community establish their rules?  What does Jackie want?

If you like this, try: Layer Cake, American Buffalo and Lock, Stock, and Two Smoking Barrels