Don’t call me ‘Whitey’

James “Whitey” Bulger, the ruthless Boston crime boss who for more than 15 years was on the FBI’s Most Wanted Fugitives list before his 2011 arrest, has been portrayed in a number of movies and TV series. Most notably, Jack Nicholson played a loose version of him in Martin Scorsese’s The Departed (2006), itself a loose adaptation of the 2002 Hong Kong thriller Infernal Affairs. Recently, gossip site Gawker referred to the latest attempt to portray the Bulger story, Scott Cooper’s Black Mass (in national release 8 October) as The Departed 2: Black Mass. The joke is unkind: The Departed, another disappointing late-era Scorsese film, managed to be both overbaked and convoluted, collapsing in its final 20 minutes into utter ridiculousness, and Nicholson’s Frank Costello was all lazily garish schtick. Black Mass, lean and understated, is the better film.

It’s also better than Clint Eastwood’s overrated Mystic River (2003) and two Ben Affleck–directed films: Gone Baby Gone (2007), which has some real sparks, and The Town (2010), which is ultimately silly and obvious. All these films are in love with the grittiness of Boston. But the patina of decay and dockside desolation alone does not a great film make. In Black Mass, cinematographer Masanobu Takayanagi captures the same wintry visual jumble as his predecessors, and Tom Holkenborg (aka Junkie XL) complements the palette with a beautifully moody soundtrack. And yet this film has an extra element: Mark Mallouk and Jezz Butterworth’s script is simpler and less hysterical than its aforementioned cousins and second cousins. It’s wordy, though not as densely talky as those great old-school Sidney Lumet films like Serpico (1973) and Prince of the City (1981). Where The Departed feels primarily like a performance vehicle, Black Mass is something more akin to a deft moral parable, which just so happens to contain excellent performances.

Johnny Depp plays Jimmy (Bulger hated the nickname “Whitey”), who ran amok in Boston for nearly three decades before his 1994 disappearance. Smart and opportunistic, Jimmy began his life of crime as a simple South Boston thug. He leveraged his way to power, regularly stepping into vacant positions left by an older generation of (mostly) Irish-American criminals who happened to be tearing themselves apart. But Jimmy didn’t just allow the happenstance of violence to land him his “promotions”; he was an instigator and innovator in the field. He knew that to be an effective leader, one had to walk the walk of violence, not just talk the talk. He did all of this rather flamboyantly, and by the mid ’70s was riding high. Jimmy’s brother Billy (Benedict Cumberbatch) was a Massachusetts senator, and the film leaves largely unexplored the question of whether Billy’s sway might have kept the focus off Jimmy for so long. It posits that the FBI did that job quite admirably all on its own.

Joel Edgerton is FBI agent John Connolly, who also happens to be a “southie” and grew up with the Bulger brothers. The story goes that Jimmy and Billy once helped Connolly out of a schoolyard scrap. As the film starts, Connolly – not exactly a pure idealist, but certainly more bushy-tailed than at film’s end – has a bright idea. He can use his street smarts and his personal history to connect with Jimmy. His dream is to cultivate Jimmy as an informant. Jimmy can feed the Feds valuable intelligence about the Boston mafia. Surely those Italian rascals are the real problem here.

Connolly sells his superiors on the idea (including Kevin Bacon, in fine form after the disastrously wrong-footed television series The Following). And that’s to be the heart of this film: in giving Jimmy leeway because he was a “Tier 1” informant, the system allowed him to become much more than a hoodlum.

With the possible exception of his blink-and-you-miss-it role in Oliver Stone’s Platoon (1986), Depp has never really played a role without some degree of levity or loopiness. His Jimmy Bulger is a chilling turn. He’s almost unrecognisable, with his thinning hair, pale skin and piercing blue eyes. On paper you’d think this is a thankless role for Depp – or any actor, for that matter – since Jimmy as scripted is a resolutely one-note character, a humourless sociopath with a PhD in menace, who undergoes no great change. And yet it’s an unnervingly watchable performance, perhaps because that menace is for the most part so eerily restrained. (Then, when it’s not, it’s definitely not; there are moments of sickening violence.)

Depp is an unhurried performer. When that quality dovetails with the film he’s in, it can work well. At his best, as in the Pirates of the Caribbean movies, it’s something that can resemble fun. At his worst, his performances can seem bloodless; there are films in which he appears to be going through the motions of some arc known only to himself. In Black Mass the bloodlessness fits. But it is Edgerton who has the meatier role – since his choices, unlike Jimmy’s, involve uncertainty and moral doubt – and he delivers its continual shifts with great subtlety. His John Connolly might actually believe for a while that, compared to the Italians, Jimmy’s not so bad. It’s a career move, too: Connolly gets kudos for even managing to bring Jimmy in as an informant. For a while, everybody’s happy.

It’s Connolly’s wife, Marianne (Julianne Nicholson), who first starts noticing the changes. He dresses differently. He wears flash watches. “You’re walking differently,” she says. He bristles. “Like it or not, Marianne,” he reminds her, “you married a street kid, and the street taught me that you give and you get loyalty from your friends.” When Connolly has Jimmy and Billy around for a barbecue, Marianne is pissed off: the flash watches are one thing, but she knows these are bad men, and he’s “socialising” with them.

“I’m not socialising!” whispers Connolly in the kitchen, the men outside on the deck.

“What do you call drinking beer and eating steaks?” snorts Marianne.

“I’m maintaining my relationships with my informants,” says Connolly – and there’s both ice and pleading in his voice.

His moral decline is inexorable. “It’s a little white lie,” he says, of one particular “version” of information, “to protect the bigger truth.” Elsewhere, clinging desperately to his own diminishing hype, he tells his FBI co-workers, “We are bringing down the house, men. La Cosa Nostra!” (The real Connolly, who retired from the FBI in 1990, was sentenced in 2009 to 40 years in prison for his various Bulger-related transgressions, including murder and conspiracy to murder.)

Everyone’s obsessed with ratting. Ratting will get you killed. “I’m not a rat,” says Jimmy’s henchman Kevin Weeks (Jesse Plemons) in a brightly lit FBI interview room. “I want that on the record.” “OK” replies the off-screen FBI agent. “You’re not a rat. It’s on the record.”

One of Jimmy’s offsiders, Steve Flemmi (Rory Cochrane), has a stepdaughter (Juno Temple) who’s a prostitute and drug addict; Jimmy murders her on the mere suspicion she’s likely to rat. A different henchman, knowing he’s about to die, pleads to Jimmy – he had no choice. “You always have a choice,” Jimmy tells the blood-smeared lackey. “You just happened to make the wrong fucking one.” He strangles the man to death. The act is not nonchalant, since – as we clearly see in the rather grim scene – it takes a lot of effort to do that. But Jimmy’s attitude to the man’s death is.

“Pull out his fucking teeth,” he says casually to his underlings. “Bury him next to the whore.”

Dramatically speaking, it’s the hypocrisy more than the violence that interests Cooper and his screenwriters. If all criminal activities are forms of dishonesty and deception, then at what point does the age-old notion of “honour among thieves” carry any moral weight? “Ratting” is at the heart of the film, and yet Jimmy, its greatest exponent, the film’s moral monster, is able to see himself more heroically as a capitalist-soldier. “It’s a business opportunity,” he tells Steve Flemmi. “We get the FBI to fight our wars, against our enemies.”

If the “good guys” can fight Jimmy’s wars, perhaps that leaves him free to be invisible. When his son gets in trouble for hitting another kid at school, Jimmy leads him, like a defence attorney giving friendly cross-examination, to the lesson to be gleaned. “Punch people when no one’s looking,” says his son.

“That’s right,” says Jimmy. “If no one sees it, it didn’t happen.” And yet his own invisibility cloak did not come with a lifetime warranty.