Dennis Lehane’s new film The Drop takes the acclaimed author-screenwriter back to the underworld of bleak, blue-collar criminals. Unlike Southy-based Mystic River and Gone Baby Gone, which were adapted from Lehane novels by other scripters, The Drop is set in the neighborhoods of ethnic Brooklyn and was adapted by Lehane himself from his own short story—a first.

He’s written plenty of scripts, having honed his craft in the crucible of HBO’s acclaimed show The Wire, but he’s never liked adapting his own novels. It’s too painful, he says, to retroactively constrain the breadth of a novel into the tight limits of a feature. But a short story fits the form.

The Drop tells the story of Bob Saginowski (Thomas Hardy) a sweet, desperately lonely bartender struggling with a past murder weighing on his conscience. He works at his cousin Marv’s bar (James Gandolfini, in his final film appearance), which is now “owned” by a Russian syndicate that uses the place as one of a network of money “drops.”

Lehane spoke with the Writers Guild of America West website about why adapting his own novels is like operating on his children, his early struggles to find his own voice and how, at the risk of sounding ridiculously “L.A.,” there really is a Zen to his writing.

I know this was a short story of yours that would represent the first time you adapted yourself, but is this also your first screenplay to be commercially released?

Yeah, it’s been a really weird history. It actually started as a novel, and then that just wouldn’t quite come together. Most of the characters you meet were there in the novel, but I just couldn’t make them come together. I had a whole bunch of characters I was in love with but couldn’t find them a story, except that I had one guy that had found this dog. I didn’t know anything else about it. He found a dog in the trashcan. Then seven, eight years later—I can’t even remember how long it was—I just couldn’t get that opening out of my mind. So I went back and adapted it as a short story. I thought I would at least tell that one little story… And then when they came to me and asked me to adapt it, I thought, Oh wow, this is really cool ‘cause now I get to blow it up. Whereas, I don’t like to adapt my books because then [you’re being asked] to compress.

You likened it to operating on your children.

Yeah, and it is. I only want to tell an organic story. So if I knew how to compress the story, then I would have written a short story, not a novel. It’s just I’m the wrong guy for [that] job. When they say, take that thing you wrote as a novel and turn it into a movie, I’m like, “Well shit, if I knew how to do that, I would have done that a year ago.”

As a novelist, what turns you on or is challenging about such a comparatively confined space of screenplay?

Exactly, that—there’s the challenge. A novelist gets to do the really gradually unraveling, or unwinding of a story. With a script, it’s like writing a short story. That’s where people miss it. [People] make the comparison [of] novel to film. No. It’s novel to television show. A novel is the season of television show, particularly in this new great era for TV, whereas, [a feature script] is a short story. So the challenge of a short story for me was always hitting the ground running. There’s literally no runway. There’s no buildup. You just got to come in and you got to nail it and then get out. That’s really the same as a film.

Novel is to TV as short story is to feature.

Well, particularly with the cable model, [where] you’re thinking 10 to 13 episodes. That really feels so much like a novel. You know, basically 10 60-page chapters. There you got a 600-page novel. It’s just a very different beast to do a script because that’s very much like a short story. You have a limited amount of C storylines in a film. You got to keep those really tight. And it’s really mostly just a storyline.

There’s something classic about the main character here, Bob Saganowski—he’s like part Rocky part Chauncey Gardner, you know? Did you model him on any characters?

I started with this idea very early on in the novel stage that loneliness kills more people than cancer. I wanted to write about somebody who was just deeply profoundly lonely, and I started there. As I progressed, I began to think a lot about Ernest Borgnine as Marty. That was the vibe. He’s this guy who doesn’t even know how to articulate how badly he needs to be touched.

He’s also caught in this no man’s land between lonely heart, human being, and killer.

Right. Well, there’s also sort of a meditation on Catholicism and religion and what it means. So here’s Bob, who’s made this choice to truly live the tenets of Catholicism to pay for his sins, and the worst thing he can give himself as penance is a lifetime of aloneness. The story begins when he’s just starting to think it’s too tough. I’ve lived this lie. I’ve lived this penance for 10 years now. When is it enough?

How often do your stories, whether they be novels or short stories, how often do they begin with a moment or a simple situation you envision that you then grow the plot from?

Always, and that’s why I think I’m a better, more natural novelist.

Because it gives you the time to let it unfold?

Plot is the last thing that ever occurs to me. You know, it’s like, Okay, who are these people and what are they doing and how do I feel in this moment? How do I depict and clarify for the reader the heart of this character in a scene? But I’m not thinking about how that scene links onto the story necessarily yet. When I talk to really great screenwriters, or really great short story writers, that’s not how they’re thinking.

Have these years of film success and TV writing changed your relationship with plot and structure at all?

Only how I approach a script. They haven’t changed in terms of how I approach a novel. I still approach a novel with a completely messed up, boy-I-hope-I-get-there-and-find-the-plot-at-some-point way.

How many times have you found yourself in the middle of the proverbial woods—just utterly lost with one of your novels?

Usually, once a book and then you sort of muddle your way through, usually. It’s a big act of faith, and you say, “I’ll get there, I’ll get there.” This was the only book that it didn’t happen. Until I had to go through this weird process to figure out what story I was trying to tell. I had to tell it as a short story, then write it as a script. Then I had to say, “Ah ha! Now I can open it up for a novel.”

You teach as well. Do you recommend this approach to others?

No. God, no. I’d never recommend this. I say that all the time to students, “Please, don’t ever follow my process. Here’s what I would recommend. Here’s what I understand works best. Please try this first.”

And the “try this first” version is like an outline?

Outlines don’t work for me. They work for me when I’m writing scripts. It’s really weird because structure is everything. So I have to outline in a script and definitely in teleplays—that’s how I was trained. I was trained basically on The Wire. That’s where I learned, that was my grad school. What we did there was, you beat the episode out. You sat in a room until you had it, until you had all your 56 beats and then you put those in an outline, and then you went home and you wrote it. So I cannot write a screenplay or teleplay any other way. I have to beat it all the way out. I try that in a book and it is always a complete disaster.

Do you lose the mojo and magic of accidentalism?

Yeah. You lose the magic. You lose the happy accidents that to me are sort of the reason why I write novels, those wonderful things that happen that you never saw coming. It gets so ridiculous to talk about. It’s very Zen. It’s very much sort of The Drop. I mean, the last line of The Drop is you can’t control it, basically. It’s a Buddhist book about Catholicism, you know? And it’s the same vibe about writing for me. When I write a novel, I have to trust my subconscious to do the job I was trained to do.

So you have to do that act of surrender?

Yeah or you miss great things… I can outline a bait, I can take a note and slap it on a 3x5 card and put it aside, but that has never shown up in a book as the thing, the moment. The moment to me is always something that happens somehow in this Zen state of freeing my mind and then all of a sudden it’s, Ah, that’s what you were trying to say. There we go.

I think for some screenwriters even are afraid they’re gonna close the door to that magic thing that just wouldn’t have happened if they scheduled everything out.

Yeah, yeah. Even now when I write outlines for my scripts or for my films, I realize that I’m still gonna be painting outside those lines. But at least I have the lines and then I go to work and then all of a sudden it’s like, Ooh, all right that’s pretty cool. That’s not up on a 3x5 card right now, and I just wrote it into the script.

What would you say the story’s about in finished form?

You know, I think the story’s very much about people sort of flailing their way toward a conception of peace. Everybody’s looking for something that will settle their mind and settle their hearts, fine. The problem in the world is that when you have enough people doing that then somebody’s interests are going to contradict somebody else’s interests, and there are going to be conflicts, and in this case, violent conflict.

Do you feel like that sort of really literary, avant-garde stuff at the end of the day is either too hard or is there even a place for it today?

Oh, there’s definitely a place for it. Again, we come back to this question of what’s organic, if it’s organic, if it’s how you think, and it’s how you see the world. I don’t think William Vollmann could write any other way. I don’t think that, you know, Julian Barnes can. [Gabriel Garcia] Marquez created magic realism not because he was trying to create magic realism but because that’s how he saw the world. There was just such a push in academia to turn into that type of writer in the MFA programs and even the undergrad programs of the 1980s and probably the 1970s well into the ‘90s I bet… You had to write the 5000th story about a vaguely dissatisfied man in Connecticut. I just reached a point where I realized this is not who I am.

It was really a matter of you finding your voice?

Exactly. That’s all it is. The one thing that I really bristle at in every way, shape, and form in the literary world, is the idea that writing is one thing, that good writing is one thing. Look, good writing is one thing. It’s depth—depth of language, depth of character, depth of insight. But beyond that, it should not be ghettoized or vulcanized. I just realized that, the bottom line was, the stories I wanted to tell were really urban stories. If it had taken me to science fiction I would have gone there. I was going to go wherever the story took me, and that’s given me a very odd career, and yet it’s a career I wouldn’t trade with anybody. It’s been really wonderful for me.

© 2014 Writers Guild of America West