Black Mass, The Departed & The Art of Revision

Black Mass, The Departed  & The Art of Revision

By Jacob Krueger


Today we’re going to be looking at the new Johnny Depp movie, Black Mass.

Now this is a really extraordinary true story, based on the life of Whitey Bulger, and featuring one of Johnny Depp’s all time best performances. And we’re going to be discussing some of its most compelling scenes and the elements that made them work in this podcast.

And yet, at the same time, despite the power of Johnny Depp’s and the supporting cast’s stellar performances, there is something about Black Mass that just leaves you (or at least left me) a little hollow– a little bit unsatisfied.

So I also want to talk about what got in the way with Black Mass, and how you can learn from both its strengths and failures in your own screenwriting, particularly when it comes to revision.

If you haven’t seen Black Mass yet, please be aware that there are spoilers ahead.

At the center of Black Mass is Jimmy “Whitey” Bulger, a psychotic gangster, played by Johnny Depp who is playing both sides, secretly betraying his mafia enemies as an FBI informant; at the same time he plays the FBI, by using his connections to run rampant in the world of organized crime.

If it sounds familiar, that’s because it is. You’ve seen this story before, in a much more complicated form, in Martin Scorcese’s The Departed. In fact, Whitey Bulger was in many ways the inspiration for the Jack Nicholson character in The Departed.

And despite Black Mass’s true-life story pedigree, well written script, and excellent direction and performances this poses a real challenge for the screenwriter. A question that many of us face at some point in the writing of our stories:

What if it’s not good enough? What if it’s all been done before?

So if that question’s got you paralyzed, don’t worry! There is a long history of this happening.

And having a story related to one we’ve already seen doesn’t mean you’re doomed to failure.

William Shakespeare stole all of his stories. Romeo and Juliet is actually just a different version of Pyramus and Thisbe. And Midsummer Night’s Dream is yet another totally different callback to the exact same source material! Hamlet is just an adaptation of The Ur Hamlet. His history plays are ripped directly from history.

But in order to transcend the experience of someone having already seen this movie before, you have to have an extraordinarily strong take on the material– a take that is different from the take of the previous writers. And you have to master the art of revision, so you can build around your unique version of the story in a way that distinguishes your work from all the stuff that came before.

For example, when Brokeback Mountain first came out, this was the first time we’d ever seen a “gay cowboy” movie. And the truth of the matter is just hearing the words “gay cowboys” was enough to make you go see, or not go see, Brokeback Mountain. In order to fulfill the promise of its premise, all that Brokeback Mountain needed to deliver was the story of two cowboys whose love for each other couldn’t fit the expectations of their circumstances.

A couple of years later, another movie called The Kids Are Alright came out. And in many ways The Kids Are Alright is just another “gay cowboys” movie. Except in this case the “cowboys” are two suburban moms, trying to navigate their love for each other among the challenges and expectations of their own suburban “home on the range.”

Before Brokeback Mountain had come out, this might have been enough. But in the wake of that film, in order for The Kids are Alright to transcend the territory that Brokeback Mountain has already trodden, it has to be more than just another “gay cowboys” movie. It needs a different take, a more alarming element at its core that distinguishes it from the movies that have come before.

In The Kids are Alright, the added element is more than just the fact that these “cowboys” are women with children. It’s that Julianne Moore’s character starts having an affair with the biological father of their kids.

You can see how this takes the “gay cowboys” story to a completely different level.

In a way, the writers of Black Mass tried to do the same thing by finding a different element around which to build their Whitey Bulger story than the one at the center of The Departed.

As you probably remember, what makes The Departed so shocking and complicated is the three levels of double crossing at the center of the structure, two of which we are completely aware of, and the third which catches us completely by surprise.

On the first-level of double crossing, we are aware that Jack Nicholson’s character has put Matt Damon’s character through the police academy in order to have a spy on the inside of the police department.

And on the second-level of double crossing, we are aware that Leonardo DiCaprio’s character has infiltrated Jack Nicholson’s gang in the desire to bring him down, and the whole “Donnie Brasco” story that is playing out between the two of them.

But until the very end, we’re completely unaware of the third level of double-crossing: that Jack Nicholson is playing everybody by secretly working as a police informant. And these three levels of complication, and these three levels of drama and excitement are the things that make The Departed so effective and so shocking.

Even though Whitey Bulger’s story, unlike The Departed, is actually a true story, trying to tell it in the same way as The Departed can only be disappointing. Because unlike the three levels of betrayal, and the three levels of structure, captured in The Departed, Black Mass only has one level of structure with which to play.

So, instead of stealing the structure of The Departed, with its three layers, and its shocking revelation at the end that Jack Nicholson’s character has been betraying everybody, Black Mass begins, wisely, by inverting that surprise ending structure, and laying its cards on the table from the very first scene.

Rather than saving Whitey Bulger’s role as an informant as a secret for the end, the writers of Black Mass begin their screenplay with the moment where he’s brought into the fold as an informant, by his old childhood friend, now FBI agent, John Connolly (played by Joel Edgerton in the film).

And by inverting the structure in this way the writers develop a completely different take on the material based on a completely different theme.

The theme of The Departed is unforgettable. If you remember that final moment in The Departed, with the rat crawling across the windowsill, you know that’s what The Departed is about. The Departed is about rats. The Departed is about people betraying, betraying, and betraying everybody around them. The Departed is about a world with no loyalty in which you can never tell who’s playing which side.

And the audience’s experience of that movie reflects the journey of the main characters in relation to that theme, learning, along with those characters, that you can’t trust anybody.

When you’re developing a take on a movie, a lot of people think that take begins with an external hook– the thing that sounds cool to the audience. But the external hook is only going to take you so far.

The truth is that the external hook is developed from the internal hook, the thing the movie is really about for you. We call that internal hook theme, and once you understand the theme you’re building, your job is to revise and revise and revise your script around that theme, until it’s present in every element: from the structure of your character’s journey, to that simple

line of dialogue, to the overall hook of your film.

That’s the thing that brings order to the chaos of a screenplay. That’s the thing that brings a feeling of unity to your audience. And ultimately, that’s the thing that’s going to distinguish your script from all the other versions of this story that have gone before it. The “what’s it about” for you, that’s different from that “what’s it about” for any other writer.

If betrayal is not a big issue in your life, the fact of the matter is you cannot write The Departed, or at least you cannot write The Departed in the way that The Departed was written.

You can’t build a hook, and you can’t build a take around something that doesn’t matter to you. And if you try, what you’re going to find is that is that rather than treading new ground, you end up retreading the old. Rather than building your movie around your own personal emotional truth, using fiction to capture the emotional resonance of your own personal life experiences, your own strange obsessions, and the questions that keep you awake at night, you’re instead repeating other people’s truths exactly the way you’ve seen them in other people’s movies.

The hook begins with the why— the why you’re writing it.

So, The Departed is a movie about betrayal. And in The Departed we see the structure is built out of betrayal. We have the structure of the Leonardo DiCaprio character and his journey in relationship with betrayal (the Donnie Brasco Story). We have the Matt Damon character and his journey in relation to betrayal. And then we have the Jack Nicholson character and his journey in relation to betrayal. And you can see that the theme ties together both the hook, and the structure, and the surprise ending of The Departed. That these things are not external things designed to make the audience happy, or part of some external formula dictated by some screenwriting book or software program, that these are internal things, organic to the why of why the writer is writing it.

In Black Mass, by inverting the structure of The Departed, and “giving away the surprise” of Whitey’s role as informant from the very first page, the writers are basically telling us, that’s not what the movie is about.

Black Mass is a movie about something else. And that’s a smart move in a film like this.

Because the fact of the matter is, you can’t outdo The Departed when it comes to writing a movie about shocking betrayal, especially not if you’re dealing with the same essential plot elements.

From the very first moment that John Connolly reaches out to his old childhood friend, Whitey Bulger, whom he refers to as “Jimmy”, and enlists his help to put their mutual enemies, the Italian mafia, in jail, the writers are telling us that this is not The Departed we’re about to watch.

In fact, rather than being a film about betrayal, Black Mass seems to be a movie about friendship, about loyalty, about childhood and family connections. A movie about a world in which Senators, and FBI agents, and psychotic mobsters are all inextricably connected by memories and loyalties that started on the playground.

And the best moments in the film are the moments where the screenplay is actually fulfilling that theme.

And you can also see why the film feels so unfulfilling at the moments where it strays from that theme.

Because without the theme of friendship, what we essentially have here is John Connolly playing the Matt Damon role from The Departed, without the benefit of the second layer of the Leonardo DiCaprio story or the third layer of the surprising ending when Jack Nicholson’s informant status is revealed. So, without the theme to tie it together, we basically have a set up that is 1/3 of the hook of The Departed.

And if you’re going to build a movie that only has 1/3 of the hook of The Departed, then you need to use that hyper focus to push that version of the story to a place it never could have gone in The Departed. You have to push the journey of these two friends, in revision after revision, further than you could have imagined it ever could have gone when you sat down to write it. And you need to push it around a theme that actually matters to you.

If you look at Black Mass, the most successful scenes in the film take place when those elements of friendship and loyalty are pushed to the extreme.

For example, the unforgettably disturbing scene between Jimmy and John’s wife.

John has invited Jimmy over to his house for dinner. And John’s wife, Marianne, doesn’t understand her husband’s connection to this man. She’s disgusted and furious that her husband has invited this psychotic killer into her kitchen. In fact, she refuses to come to dinner and locks herself in her room. John does his best to makes excuses for Marianne, telling Jimmy that she’s sick. But Jimmy isn’t having it. He stalks up to her bedroom, and bursts in on Marianne in one of the creepiest scenes in recent film history.

On one level, in his own psychotic way, Jimmy wants to protect his friend. “You’re humiliating your husband in front of his friends,” he tells Marianne, while playing his own game of humiliation with her.

And on another level, Jimmy is delighting in his own little humiliating power game, as he lecherously runs his hand over her face to “check her temperature,” scares the life out of her by choking his hand around her neck to “see if her glands are swollen.” It’s one of the most complicated character moments in the film, a mix of love for John, and complete disregard for him. A mix of concern for John’s dignity, and complete power over him, his wife, and every aspect of his life.

These are the moments at which Black Mass thrives. But, unfortunately, the structure of Black Mass fails to build around these moments in a way that can tell us what the movie is really about. Why all this matters, beyond the alarming fact that much of it actually happened.

Perhaps that’s because, despite their obvious talent, and the elevating performances of the entire cast, at this phase of the script, the writers don’t seem to know what it’s really about themselves.

Is it about the friendship between John and Jimmy, and how his loyalty to his friends turns a good man bad?

Is it about the frame of interviewee after interviewee, telling the story of their compatriot while insisting they’re not rats?

Is it about Jimmy’s love for his son, and how the moment of his son’s death pushed him over the edge from a beloved guy who cared about the neighborhood and took care of little old ladies, to a psychotic killer who didn’t care about anybody?

Is it about Jimmy’s relationship with his mother, and his brother, and the strange legacy of this woman who cheats at cards and who came from nothing, and raised Boston’s most powerful criminal and most powerful senator under the same roof?

Is it about a well meaning FBI agent losing his soul, not to greed, but to loyalty?

Or is it about an old man finally getting captured for the sins of his youth?

There are so many wonderful threads that could have been developed into powerful hooks and powerful themes in this movie, but instead are left dangling. Not because they aren’t powerful, but because the writers failed to decide which ones really mattered for the story that they wanted to tell.

The key to revision is focusing on one thing that really matters to you.

The mistake of these truly talented writers is simply that they are trying to do it all. Repeating the common mistake of biopics of trying to squeeze the whole story into 105 pages (this happened, then this happened, then this happened), rather than getting deep into the one piece of the story that made all the other pieces matter.

What we’re seeing when we see Black Mass is in many ways a promising early draft in desperate need of a thematic revision. Like many early drafts, it has brilliant moments, compelling characters, and enough elements to tell a dozen stories.

But it lacks the central thread that ties it all together, makes the story matter to us, and distinguishes it from the other versions of the story that have gone before.

Revisions are about hard choices, and revisions are about theme. Revisions are about picking one thread, and developing it as deeply as you can, even at the cost of “killing your darlings” or losing scenes that you love.

All scripts start off as early drafts. And all scripts must go through revisions, before the cliches give way to insights, your personal truth starts to transcend the truths you’ve seen in other films, and your story starts to matter.

Revisions are about taking yourself, and your character, deeper into the wilderness of your own personal questions about the world, than you ever imagined when you first set down to write them. In order to create a journey that changes the character, yourself, and the audience watching them, just by having witnessed it.

So next time you start wondering “do I have what it takes?” “Has this all been done before?” or “Is this a movie worth watching?” remember that you’re asking the wrong questions.

The real question is: “What is this movie about to me? Why do I want to write it?”

If you’d like to learn more about using theme as your guide in a revision, check out our upcoming seminar with Jessica Hinds: Mastering the Rewrite: Theme.


Leave a reply

Your email address will not be published. Required fields are marked *


Welcom Back!

Log in to access your account

Our website uses cookies to provide a better user experience. By using our site, you agree to our use of cookies. Learn more about cookies and how you can refuse them.

Your seminar link is on its way to your inbox.

But wait… that’s not it!


Join award-winning screenwriter, Jacob Krueger, and industry pros for an hour of writing lessons and guided exercises. Every Thursday, via Zoom.

Sign up below for this Thursday’s class!



Registration Information

Booking Summary

x RSVP (Free)
Total Price


We will see you this Thursday!

7pm ET / 4pm PT

Check Your Email For The Link

(Don’t see it? Check your spam folder)

Donate To Our Scholarship Fund

We match every donation we receive dollar for dollar, and use the funds to offset the cost of our programs for students who otherwise could not afford to attend.

We have given away over 140,000 of scholarships in the past year.

Thank you for your support!

Other Amount? CONTACT US

Get Your Video Seminar


Where should we send it?

"*" indicates required fields

Would You Like More Information About Our Classes?
This field is for validation purposes and should be left unchanged.

Need A Payment Plan?

We like working with artists and strive not to leave writers behind over money.

If you need a payment plan or another arrangement to participate in our programs, we are happy to help.

Chat us or give us a call at 917-464-3594 and we will figure out a plan that fits your budget.

Join the waitlist!

Fill in the form below to be placed on the waitlist. We'll let you know once a slot opens up!