Black Mass: How the life and crimes of James 'Whitey' Bulger brought out a striking performance from Johnny Depp

But spare a thought for Sienna Miller, who ended up being cut entirely from the biopic

Gangster: Johnny Depp in a scene from 'Black Mass' (Warner Brothers)

Hollywood was always going to make a film about the life and crimes of James “Whitey” Bulger. The notorious US mob boss, whose crime empire ruled South Boston for three decades through murder, drug trafficking and extortion, is prime biopic territory. After an aborted attempt by Ben Affleck and Matt Damon to make their Whitey Bulger film, now arrives Black Mass, with Johnny Depp playing the Irish-American gangster and Benedict Cumberbatch co-starring as his upstanding politician brother, William Bulger.

Black Mass both chronicles a criminal psychopath and examines how someone who ended up the FBI’s second-most-wanted man, behind only Osama bin Laden, evaded prosecution for so long because Boston’s law-enforcement agencies allowed it. Bulger was an informant for the FBI in its quest to bring down the Italian Mafia. The title of the film, adapted from a book by Dick Lehr and Gerard O’Neill, refers to the unholy alliance between the FBI and the man the authors call “God’s gift to gangsterhood”. Bulger was eventually convicted of 11 murders and other crimes in 2013 and is serving a life sentence at a federal penitentiary in Florida.

Director Scott Cooper compares the mythology of Bulger’s Winter Hill Gang to the Krays. “One of the things that intrigued me was that lawmen and criminals in South Boston in the 1970s and 1980s were virtually indistinguishable,” he says. Central to Black Mass’s complicated liturgy is, of course, Johnny Depp. He has swapped Pirates of the Caribbean and eccentric Tim Burton films for his best role since his performance in another gangster film, Mike Newell’s 1997 hit Donnie Brasco.

Johnny Depp with the film’s director, Scott Cooper (Getty Images)

To play Bulger, Depp covered the upper half of his face with prosthetics and wore 50 different hairpieces to capture his receding hairline. “Johnny Depp is one of the most famous people in the world and everybody know what he looks like,” says Cooper. “He doesn’t look like Whitey Bulger! When Johnny came to set on the first day of shooting, many people who knew Whitey were there and were shocked by the transformation. They said he was chilling.” His co-stars thought the same. Joel Edgerton, the Australian actor, plays Bulger’s FBI handler and childhood friend John Connolly, who was imprisoned for tipping him off that he was about to be indicted. He says: “I first met him as Johnny with the tattoos and denim jeans, the iconic stuff I grew up with. But the majority of time I spent with him on set he was Jimmy. It didn’t feel like there was much Johnny there at all.”

“I only saw Johnny in his full Whitey personality,” adds Dakota Johnson – fresh from Fifty Shades of Grey – who plays Lindsey Cyr, the mother of Bulger’s son, who died of an illness at the age of six. “He had this force, this blast of energy and it was a magical experience. It wasn’t something I was afraid of.”

When I briefly caught up with the man himself at Black Mass’s Toronto Film Festival premiere, the 52-year-old was revelling in the depth of a role that is tipped to land him his fourth Best Actor Oscar nomination. “Whitey was a fascinating figure who considered himself honourable,” Depp said. “In a weird way, [the role] stays with you for life when you have investigated and done a lot of homework about this person. I thought about him constantly.”

Cumberbatch also did his homework to play Billy Bulger, a Democrat who served 18 years as president of the Massachusetts Senate. “Like all the great actors, Benedict cares about research,” says Cooper. “Billy was a public figure and Benedict nailed this Kennedyesque front that Billy puts forward. Any time I visited his trailer or his apartment in Boston, he was watching footage of Billy and mimicking him.”

Cumberbatch took the role to heart. “We had dinner with Benedict last summer,” says Dick Lehr, the co-author of Black Mass, the book on which the film is based, “and I was impressed he was working so hard for the role and was even nervous that he wouldn’t get it right.”

Cumberbatch usually plays mavericks and anti-authoritarians such as Julian Assange or Sherlock Holmes, not pillars of the community; here he is Polonius as opposed to the Hamlet he has just played at the Barbican. “He is strong and confident in this, political and ambitious,” says Julianne Nicholson, who acted with him in both Black Mass and August: Osage County. “He couldn’t be more different to his character in August.”

Black Mass was filmed in Boston, where feelings about Bulger still run high. “When I arrived in America,” says Edgerton, “the guy stamping my passport was from South Boston and he knew I was an actor. I told him what I was about to do and he said, ‘You better not fuck it up!’ As I was walking away, his next customer said, ‘Don’t fuck it up!’ Then Edgerton began filming and things got stranger. “In the screenplay there is a line where my wife says I get manicures. I actually met someone during the shoot who said her friend ran a nail salon where John Connolly used to get manicures. I thought that was in the script to add a little pizzazz – but it turned out to be true.”

James “Whitey” Bulger as a young man (AP)

Black Mass has received a mixed reception in the US. Kevin Weeks, Bulger’s erstwhile right-hand man, called the film a “fantasy” while The New York Times wrote that it “feels more like a costume party than a costume drama”. Yet in addition to Depp and the tribal triangle with the FBI and his brother, the film has a vivid rogues’ gallery of supporting characters. Kevin Bacon, Corey Stoll and Peter Sarsgaard are among those who appear as assorted gangsters and law-enforcement agents, many of whom fall fatally foul of Bulger. Sarsgaard enjoys a particularly memorable cameo as Brian Halloran, a doomed hoodlum. “He is someone enjoying the lifestyle of being a criminal who just wanted to do drugs and get girls,” he says. “He was more into the party of being a gangster and less into the death!”

Wives and lovers of the lawbreakers and lawmakers play a prominent role in the film via Johnson, Nicholson and Juno Temple. “Normally in gangster movies, the female roles are mostly narrative constructs made simply to move the story along or to be an enticing sparkly thing in the corner of the frame,” admits Johnson. “Not so here.”

Much of the credit for the richness of Black Mass’s characterisations goes to co-writer Jez Butterworth. Depp is seemingly an aficionado of Johnny “Rooster” Byron, the protagonist in Butterworth’s play Jerusalem. “Once Depp got attached [to the project], Jez came in and added the police interview scenes [which recur in the film],” says the film’s co-writer, Mark Mallouk.

Bulger went on the run for 17 years before being caught in California in 2011. During his time on the run, he was reputed to have visited London and writer-director Heywood Gould (Cocktail, The Boys From Brazil) reports having seen him in LA a few years before his capture. “I saw him walking on the promenade in Santa Monica, wearing jogging pants and a sweatshirt, and he gave me a look that chilled me. My family didn’t believe me, but he was arrested near there a few years later.”

Yet Sienna Miller, who shot scenes as Bulger’s girlfriend Catherine Greig, who was living with him while on the run, was entirely cut from the film when Cooper opted to end proceedings with Bulger’s flight from Boston in 1994. “I wasn’t telling the story about what Whitey did when he disappeared because that’s a very undramatic part of his life,” Cooper says. “Unfortunately, because of that Sienna’s character was collateral damage. She gave an outstanding performance and she and I will work together many times.”

Mallouk adds: “Maybe that’s a different movie: Whitey’s version of a love story. You have to kill your darlings and leave stuff on the battlefield.”

Ultimately, Black Mass revolves around Whitey’s war with the world, supported by the uneasy peace he formed with the FBI. “Johnny Depp largely plays likeable and larger-than-life characters,” says Cooper. “I wanted a certain chillness and power and Johnny bravely embraced everything Whitey was.”

Bulger may no longer be hiding in California, but should the lawless bishop of South Boston end up worshipping at the Academy Awards altar in February? l

‘Black Mass’ is released on Friday