Johnny Depp as Whitey Bulger in Black Mass and Jack Nicholson as Frank Costello in The Departed.

‘Black Mass’ and ‘The Departed’ bring Whitey Bulger to the big screen

Following an unusual train of thought off my post from earlier this week about Trumbo and Hail Caesar and how they took the story of communism in Hollywood to the big screen in decidedly different ways, I’ve decided to look at a different pair of films that take on the same subject matter: The Departed and Black Mass. That just about ends the similarities between this post and the previous one though, as the esteemed mob leader Whitey Bulger has very little to do with either Hollywood or communists.

I guess the one other similarity I can draw to the earlier post is that like that pair of films, this coupling also sports one that adapts the true story literally and another that fictionalizes it, bringing in basically no real life personages or names. This year’s Black Mass from writer-director Scott Cooper (Crazy HeartOut of the Furnace) is the traditional adaptation in which Johnny Depp becomes the first actor to play the namesake of Whitey Bulger. The Departed is a complex film with so many far-reaching influences that it is hard to pin down exactly what esteemed director Martin Scorsese was trying to do with the project. Many will argue that he succeeded as that film won him his only Oscar to date. But in my opinion Whitey Bulger is a fascinating story that has yet to be executed in an entirely worthy film.

Leonardo DiCaprio, Jack Nicholson, and Matt Damon in an eerie promotional poster for The Departed.

Scorsese’s The Departed is all over the place

It’s pretty hard to believe that it took thirty years for the director of Taxi Driver to take home an Oscar. But that’s exactly how it panned out for Martin Scorsese. Unfortunately, following several masterpieces that include but are not limited to he aforementioned De Niro collaboration, Raging Bull, The Last Temptation of Christ, Goodfellas, and many other more worthy features, Scorsese was finally rewarded for his least thematically or stylistically cohesive film, one that feels more like an overblown studio production with seven writers than a loose tone piece like the best of his work.

In my opinion, the best work of Scorsese is Goodfellas. But even some of his second tier works like Casino and The Wolf of Wall Street retain what I consider to be the organic feel of a fully realized Scorsese feature. Notoriously lacking in traditional narrative structure, I’ve always found Scorsese’s greatest strength to be creating the feel of a world and filling it with rich characters. He’s great at capturing the drama of a moment, like when Joe Pesci loses his temper and shoots a bartender to death just for talking back to him in Goodfellas. The scene in a split second goes from laughter to disturbed frustration. It doesn’t really contribute to any major plot thread. But it lets us see the disorder and lack of value of life within the gangster world. The tension is palpable to the audience.

The Departed offers no such sequences. In fact, I’d argue that Scorsese wasn’t sure what he was trying to offer with this film. It opens with a voice over from Frank Costello (Jack Nicholson in the Whitey Bulger-ish role) in which he reminisces on the “old days” and referring to the gang as the “church.” At one point Scorsese had expressed interest in this film being a full history of the Irish mafia in Boston. I’m guessing this inexplicable reflection that doesn’t return in the film in any form at all is a left over piece from when Scorsese wanted to go that direction. And part of me is disappointed he didn’t. Although I don’t generally go for voice-overs, that first scene makes it look like The Departed is going for the style of Goodfellas or The Wolf of Wall Street. Alas, within a couple of minutes it takes a turn towards traditional narrative structure and it doesn’t look back.

The narrative of The Departed focuses on two characters: Billy Costigan (Leonardo DiCaprio) and Colin Sullivan (Matt Damon). The former comes from a bad family but wants to be a clean cop. The latter comes from a good family, but we’ve just seen him seduced by Costello as a child. We see them both graduate from the police academy. Sullivan quickly moves up the ranks, clearly working for Costello. Ironically, Costigan is rejected from the ranks entirely on the basis of his family’s connections to organized crime. From here, William Monahan’s cluttered screenplay moves through a three-act hero’s journey structure that has some effective narrative intrigue, but feels spread thin, lacking Scorsese’s typical lively flourishes.

The components of The Departed that are most effective narratively, such as the Sullivan/Costigan dynamic, are lifted from a Chinese film called Internal Affairs, on which the Scorsese film is based. Even though aspects of this story are fun and engaging, I think the best work of Scorsese feels less narrative than this and more chaotic, capturing the quirks and incongruences that make us human in the least likely of places. The Departed, with it’s exterior source material forcibly installed in a Boston Irish Mafia setting, is just the opposite: a melodramatic story that feels moralistically inevitable, as if a Dickensian hand of God guides it along.

This is complicated further by Scorsese’s other ambition for the film which is to make some sort of biopic of Whitey Bulger. From the extensive Bulger narrative to draw from, Scorsese focuses on the detail of Bulger being an FBI informant, probably because it was the biggest news he ever made and because I guess it is supposed to thematically compliment the plot of Internal Affairs. It’s questionable how well it succeeds in that department.

In The Departed we see the bulk of the story through the eyes of Sullivan and Costigan, the majority of our exposure to Costello/Bulger being through their interactions with him. As a result, the film saves the reveal that Bulger is an FBI informant until the last minute, when it is revealed to the characters that truth will affect most. All in all, the narrative is entertaining. But there isn’t a single memorable Scorsese sequence in the it. Each scene feels like it does the minimum to service the story which contains disparate elements from about seven film’s worth of unrelated ideas.

To add to Scorsese’s over-ambitious stuffing of The Departed, it ends with a recreation of a famous funeral shot from The Third Man. This feels suspiciously like something Scorsese has always wanted to put in a film that just randomly fell into this one despite the fact that it doesn’t make much thematic sense. Between the efforts to be a history of the Irish Mafia, the melodramatic plot of the source material, and the bizarre closing shot, the cinematic narrative of Whitey Bulger’s life feels rather watered down by the end, missing out on a lot of the most interesting elements.

Whitey Bulger talks with FBI agent John Connelly in Black Mass.

Black Mass is effective and boring in turn

Scott Cooper is an intriguing filmmaker whose work I have thus far found difficult to criticize, but more difficult still to actually enjoy. Beginning with Crazy Heart, Cooper demonstrated a strength in attracting A-list stars to interesting projects and then coaxing excellent performances out of them. He is a fine writer and a competent director, yet none of his three films at any point felt like they came to life while I was watching them.

Black Mass in particular suffers from this as it is his biggest work to date. It spans several decades and has a lot of characters to keep track of. Instead of focusing on a film sized portion of Bulger’s life, or even providing a fresh lens through which to see him, we’re given a historical rundown of what happened that lacks strong character arcs or clear relationships while also not being quite journalistic or procedural enough to justify this approach. Still, several sequences of Black Mass are effective at a visceral level even if they lack serious insight into the character of Bulger or the overall message of the film.

Black Mass opens with a member of Bulger’s Winter Hill Gang admitting to a committing series of crimes to the FBI. He’s offering to share information about White Bulger in order to secure his own immunity. This is a gag that periodically shows up in the film, usually when it is about to leap forward several years. The point is that almost every member of his gang eventually testified against him and the movie wants us to know that from the beginning. This isn’t a bad set up for the film as most viewers are likely to be familiar with the fact that Bulger was himself an FBI informant as a result of it being widely publicized and on of the few accurate details of Bulger’s story that made it into Scorsese’s The Departed. But more on that later.

It is unlikely that many are aware that once it appeared on the front pages of Boston papers that Bulger was an informant, almost everyone he knew ran to the FBI, desperate to cover their own tracks as they had no way of knowing what about them Bulger had devulged to their sworn legal opponents. So Black Mass is structured like a series of betrayed confessionals, which is an effective way to focus the film on his betrayal and introduce several of the characters.

Where this becomes problematic is that, despite the fact that The Departed incorporated very little from the Whitey Bulger story, the  one apsect that Black Mass chooses to focus on is literally the one part that The Departed utilized. As mentioned, this is a story that spans several decades and has dozens of characters and narrative threads not already brought the silver screen that are all equally worthy of attention.

But instead of go for something original, Black Mass places the strongest emphasis on two characters: Whitey Bulger and his childhood friend in the FBI, John Connelly. The dynamic between these two ends up feeling a lot like the primary relationship of The Departed between Sullivan and Costello. Sure, there are differences in that Sullivan does not know that Costello is an informant where Connelly is the reason Bulger becomes one. But the point is that Cooper made the poor choice of focusing on the part of the story that everyone already knows from the news and has already seen in a best picture winning Scorsese film.

Even with its shared point of emphasis with The Departed, Cooper’s Black Mass still doesn’t feel like it knows what to hone in on. While it remains safely in the confines of Bulger’s real life story, rather than take a small piece of it (like Ava DuVernay did with Martin Luther King Jr. in Selma), Cooper tries to tell the whole story from Bulger’s origins as a small time player to his capture in 2011 and the only lens we’re given is the one we’ve already seen.

There are so many aspects of Bulger’s story outside of his being an FBI informant that have yet to be fully fleshed out. Among these are a battle with the Italian Mafia, the death of his mother and son, and above all else his relationship with his brother who was a senator, at one time the most powerful person in Boston on the right side of the law. That last dynamic is the one I would most like to see a film focus on. And he is in the movie, played by Benedict Cumberbatch, who delivers the most awkward attempt at a Boston accent I’ve ever witnessed. But more problematic than the sound of his voice is that his character is only brought in as a middle man between Bulger and Connelly.

At no point does Black Mass thoroughly explore the relationship of these brothers who have a deep love for one another and become the two most powerful people in their world in opposite ways. In real life they maintained close relations without ever engaging in each other’s activities, helping one another along, or protecting each other in illegal ways. That story is rich with questions of morality and loyalty while not being a story we’ve seen before either about Bulger himself or any fictitious mobster. Alas, with two films in a decade already made about the infamous murderer, it looks unlikely that we will see the one I’ve always wanted any time soon.

Black Mass is available as of this week on DVD/Blu-ray, Redbox, and Amazon Rental.

Watch the trailer for Black Mass:

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