Insider Out: ‘Black Mass’ Depicts the Shifting Fortunes in Whitey Bulger’s Criminal Life

When Kevin Weeks (Jesse Plemons) begins to reveal to the F.B.I. all he knows about Jimmy (Whitey) Bulger (Johnny Depp) and the Winter Hill Gang, he summarizes the theme of Black Mass: “Southie kids, we went straight from playing cops and robbers on the playground to doing it for real in the streets. And just like on the playground, it wasn’t always easy to tell who’s who.” John Connolly (Joel Edgerton) in particular struggles to maintain a line between his childhood loyalty to Jimmy Bulger, who once saved him from a beating by neighborhood bullies, and his duty to the F.B.I. to help save Boston from organized crime.

So, too, albeit in much less screen time, does Jimmy’s younger brother, Billy (Benedict Cumberbatch). Billy has served as president of the Massachusetts Senate for 18 years and, later, president of the University of Massachusetts. He must balance his role as a tough state leader with that of a loving brother.

These three characters especially well illustrate director Scott Cooper’s and screenwriters Mark Mallouk’s and Jez Butterworth’s vision for this film: the shifting loyalties among powerful insiders and outsiders and the blurred lines between public and private lives.

In this film, Jimmy Bulger is not only a crime boss who branches out from South Boston to Miami as he expands his business from drugs and extortion (with increasingly frequent murders) to gambling on jai alai. He also becomes an F.B.I. informant for Connolly. Bulger protests that he has not become what he hates, “a rat”, and as everyone is quick to note, Jimmy metes out merciless retribution to rats discovered within his circle of friends or business associates.

Bulger instead sees his relationship with Connolly as “business” — the F.B.I., with Bulger’s occasional tip, can rid Boston of Bulger’s rivals. Along the way, his own business is protected and, over time, can claim turf from fallen foes.

Connolly begins the film as an F.B.I. golden boy, a hero who returns home to clean up the rough streets where he grew up. Early in the film he congratulates Billy Bulger on becoming a senator and questions whether he should call his childhood friend Billy or “sir”. Billy laughs as the two compliment each other on their success and marvel at how far they have come.

Nevertheless, during an increasingly stilted lunch conversation, Connolly asks about Jimmy and offers Billy his F.B.I. business card to pass along to his older brother. Ever wary when discussion involves Jimmy, Billy firmly tells Connolly that “Jimmy’s business is Jimmy’s business.” Abruptly terminating the meeting, Billy nonetheless dons his “friendly politician” face as he suggests that Connolly have dinner with his family, who “would love” to see him.

What’s surprising is Connolly further fuzzes the line between Bulger as family friend and as F.B.I. agent sworn to protect the public. During Christmas dinner with the Billy Bulger family, Connolly and his wife Marianne (Julianne Nicholson) rub elbows with politicians and crime lords. Billy and his wife Mary (Erica McDermott) promise to help Marianne meet more people and smooth her way into the insular South Boston community. When Billy leaves the room to take a phone call, Connolly tells Jimmy that he is amazed how Billy manages his nine children, and the two chuckle at his having such a large brood.

Later, Connolly (without the support of increasingly incredulous and angry Marianne) hosts a barbecue for a fellow F.B.I. agent, Jimmy, and some of Jimmy’s employees. Despite the dinner being held at the Connollys’, Jimmy is clearly in charge.

The often-blurred line between being an insider and an outsider wanting in is the basis of the slippery-slope story of John Connolly. He may be an F.B.I. insider, which makes him valuable to Jimmy Bulger, but he’s also fascinated by Bulger. Connolly increasingly becomes part of Bulger’s off-duty social network, going so far as partying with the crime boss in Miami following the take-down of one of his rivals. This fraternization opens a back door for criminal outsider Bulger to learn more about the F.B.I.

The film focuses on shifting, often oppositional loyalties (e.g., Is Connolly most loyal to the F.B.I. or to Bulger? Who is loyal first to the law and second to Jimmy? Who protects himself, and who will sacrifice himself for Jimmy?). Becoming a perceived insider into the wrong group at the wrong time leads to most characters’ downfall. If the film had been focused only on that theme of shifting loyalties as characters decide to which group they want to or should belong, Black Mass may have been more gripping.

Cinematography and the Audience as Insider or Outsider

Even the cinematography supports this insider/outsider theme. Reminiscent of The Godfather’s cinematography, with numerous camera shots of enclosed spaces shutting in the insiders and keeping out those who do not belong, Black Mass often places the audience in the role of the outsider looking in — or of someone spying on what goes on behind closed doors. When Jimmy breakfasts with the mother of his child (Dakota Johnson) and his little boy (Luke Ryan), the camera highlights the bright kitchen by juxtaposing a long shot of Bulger at the kitchen table with the darkness of the living room separating the camera (audience) and the conversation.

A similar shot is used when John Connolly kisses Marianne goodbye in the kitchen as he leaves for work. The intimacy of these enclosed family spaces is suggested by a scene’s first longer-distance shot before the film cuts to close-ups of the “talking heads” inside the room.

This technique is used in the workplace, too. In one scene, the camera provides a wide shot of a balcony hallway within the F.B.I.’s Boston headquarters, where Connolly animatedly discusses an informant. The characters almost seem to be on a stage, because the walkway is long, and the actors look small to the audience. Once again, the film next cuts to close-ups of the characters having the discussion. Bringing the audience in from the outside can be effective, but the frequent use of this technique makes it more noticeable to viewers than allowing the camera to unobtrusively pull the audience into a scene.

The camera also uses objects to create a frame around a character. The horizontal lines of window blinds, for example, allow the audience a limited but focused view of the action taking place within an office. Doorways frequently provide a frame that draws audience attention to a character. An outdoor setting can also create a frame. When Jimmy Bulger buries the latest murder victim along a riverbank, the pylons of a bridge frame the burial site and emphasize Bulger’s action. Just as with the emphasis on enclosed spaces, using the setting to create a vertical or horizontal frame can be highly effective — unless the device is overused to the point that the audience begins to notice it.

However, the cinematography is especially effective in showing audiences Bulger’s viciousness. The violence is graphic and fast paced, and an up-close perspective forces the audience to become eye witnesses to Bulger’s crimes. Whereas brains often colorfully splatter cars or pavement, the strangulation of a young woman takes place visually off camera, although her silenced protests and harsh breathing leave little doubt of what is taking place.

Indeed, Black Mass doesn’t hesitate to show exactly how horrific casual brutality can be, and to emphasize that the men who perpetuate this violence see it as an expected part of their daily business. When Black Mass takes such a clear dramatic stance, the film becomes visually memorable.

A Stellar Cast Following Depp’s Star Turn

Although the insider-outsider theme broadens the film’s focus, make no mistake, this is Johnny Depp’s movie. It likely was supposed to be the film that made the entertainment industry, as well as fans, remember just how good a “serious” actor Depp can be and to reward his performance. However, when the Academy Award nominations were read, Depp’s name was not on the Best Actor list. It was on the prestigious Screen Actors Guild list of actors vying for Outstanding Performance by a Male Actor in a Leading Role. Depp also earned a Lead Actor nomination from the Critics’ Choice Awards.

These accolades are well deserved. Depp excels in the role of Jimmy/Whitey Bulger. Jimmy can be paternally soft spoken when explaining to his son that “It’s not what you do. It’s when and where you do it and who you do it to or with.” When Jimmy sees an elderly lady from the neighborhood pulling a cart of groceries behind her, he stops his car and has his associates take her groceries home to put them away for her. During a surreal conversation, the woman casually asks “When did you get out of Alcatraz?” before beaming “It’s wonderful to have you back in the neighborhood, son.”

Jimmy indeed seems to be a good son. In an all-too-brief domestic scene in his mother’s house, Jimmy complains that Mom is cheating at cards, but he dutifully plays along while Billy prepares dinner. Domestic scenes may help the audience relate to or even empathize with Bulger, and Depp can convincingly play softer emotions, but the script often lets him down by not creating a story arc with dramatic highs and lows.

Of course, creating a suspenseful plot about a true recent story is difficult. Anyone following the news since 2011 knows that Whitey Bulger was captured by the F.B.I. after nearly two decades hiding in plain sight in California. He was sentenced to life imprisonment. Thus, the plot has no real surprises.

Black Mass also suffers from audience déjà vu, not only with filming techniques reminiscent of The Godfather but the uneasy humor of a Goodfellas. Jimmy, for example, seems to threaten one of Connolly’s colleagues during the barbecue, only to laugh and proclaim his menace is a joke. Audiences likely remember or have seen clips of a similar scene in Goodfellas or another film about organized crime.

Even when Jimmy melts down upon the realization that his son is going to die and throws chairs and upends a table in his rage, the aftermath doesn’t change him. Throughout the film, Bulger is ruthless and violent. The occasional smile or soft word doesn’t signal a personality change. Neither does grief. In the next scene, Bulger is back to mayhem. Depp can realistically express a range of emotions, but the film limits the character’s emotional depth and doesn’t build to a satisfying conclusion. Audiences are not surprised (or even particularly glad or sad) when Bulger is captured.

Perhaps for this reason, Black Mass received a great deal of attention at film festivals in Toronto and London, for example, but many critics rightly concluded that it’s a good, but not Oscar-worthy film. It benefits from a highly talented cast in addition to Depp. Edgerton received a Breakthrough Actor award at the Hollywood Film Awards and the Australian Film Institute’s nomination as Best Supporting Actor for his role in Black Mass; in 2014 he also was nominated by the Australian Film Institute for The Great Gatsby. Cumberbatch received an Oscar nomination in 2015 for The Imitation Game.

In addition to Plemons (Fargo), Johnson (Fifty Shades of Grey), and Nicholson (Boardwalk Empire, August: Osage County), the cast includes Peter Sarsgaard (The Slap) and Kevin Bacon, who plays Connolly’s increasingly frustrated boss, F.B.I. Agent Charles McGuire. These performances are a key reason to see Black Mass. Its plot may not have the requisite twists to make it a great movie, but the actors in this ensemble are uniformly good in their roles. Their “Boston” accents may make some natives smile, but they convincingly play their real-life counterparts.

The Blu-ray/DVD Extras

Another reason to enjoy the Blu-ray/DVD/Digital HD set is the range of extras. “Black Mass: Deepest Cover, Darkest Crime” provides insiders’ perspectives on how and why plot and character choices were made for this film. Director/producer Cooper reiterates “there were many vantage points from all the different players, and the truth seemed to be elusive.” Therefore, choosing how to emphasize specific milestones in Whitey Bulger’s life between 1975 and 1995 became crucial in narrowing the scope of the plot.

Producer Brian Oliver also explains the rationale for what ended up in the film, which, for film lovers, offers unique, in-depth insights into the process of structuring a film with many possible perspectives. Another highlight of this 23-minute film is the actors’ discussion of character development within scenes. Cumberbatch, for example, notes that the film is “not all about … big Socratic moments in life. There’s a minutiae. There’s a domestic reality,” which Black Mass strives to accurately portray. Some of the best scenes between brothers Billy and Jimmy take place quietly in their mother’s home.

Depp’s most quotable comments are part of the roughly 12-minute “Johnny Depp: Becoming Whitey Bulger”. Through Bulger’s attorney, Depp requested a meeting with the man he would play on screen, but Bulger chose not to participate because he was not fond of the book on which the movie was based. However, Depp was able to talk with John Connolly and men who had worked for Bulger. His research helped him to “be respectful in [my] approach to grab onto this character and hold on. You have to approach it with respect … It’s their lives, so they deserve as close to an honest version of themselves as humanly possible.”

Depp’s determination to realistically play Bulger included his willingness to dramatically change his appearance for the role. This special feature illustrates the lengthy process by which prosthetics and makeup transformed brown-eyed, dark-haired Depp into blue-eyed, thinning white-haired Bulger (who has a prominent dark front tooth). Although all extra features are included on the Blu-ray disc, only “Becoming Whitey Bulger” appears on the DVD.

Documentary lovers should find plenty to enjoy in the hour-long “The Manhunt for Whitey Bulger”. File footage of the F.B.I. manhunt and eventual capture of Bulger highlight the history behind Black Mass and underscore the filmmakers’ success in turning Depp into Bulger.

Although Black Mass is not a perfect example of its genre, it has elements — from the way violent scenes are filmed to interesting performances by a highly watchable ensemble — to recommend it. As Depp explains, “Walking that tightrope between playing a very dangerous, unpredictable, walking time bomb and an emotional, sensitive, caring wreck wasn’t an easy one.” However, that balancing act explains why Depp, if not the film, was singled out for those SAG and Critics’ Choice nominations.