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

By Tom Teodorczuk

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.

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.”