How Dennis Lehane Went From Hardback to Hollywood

The odds of getting your novel published are slim. The probability of reaching The New York Times Best Sellers List several times over is even slimmer. The odds of having not one, but multiple novels turned into critically acclaimed, high-grossing films are razor thin — unless you're Dennis Lehane. With novels-turned-films Mystic River, Gone Baby Gone and Shutter Island behind him and Since We Fell and Live by Night optioned by Dreamworks and Warner Bros. respectively, who better to discuss achieving an astounding book-to-film career at Litquake's From Hardback to Hollywood event on Oct. 12, as he did?

SF Weekly chatted with Lehane about why his books translate so well to the silver screen, how his professional goals have changed over the last decade and whether the hardcore Bostonian has finally gone Hollywood. 

[jump] Your talk as part of this year’s Litquake is called From Hardback to Hollywood. In many ways, you’ve achieved
every author’s dream multiple times over, by having several novels turned into films. Why have your books translated so well to the silver screen?

There are a couple of reasons. Most have nothing to do with me. The one thing I’ll take credit for is I write characters who really good actors seem to want to play. So, OK, there’s the feather in my cap. But everything else has been connected to the best version of the auteur theory — that in each case, you’ve had a writer-director team, not me, that was allowed to do their work with zero studio interference, once the budget was set. So there was an implicit sort of faith going on there, with Clint Eastwood and Brian Helgeland for Mystic River, with Ben Affleck and Aaron Stockard for Gone, Baby, Gone, with Martin Scorsese and Laeta Kalogridis for Shutter Island. I think that’s the reason. When you look at those films, you say, 'When’s the last time you guys were in contact?' It’s like about 18 months ago. We took a pass at the script, I gave him my notes, he took them or he didn’t and we moved on. I’ve seen what the guy can do. I’m not worried. We’ll see what happens.

Are you ever surprised about which of your novels Hollywood is interested in?

Yeah, yeah, I’ve seen that a few times. I was surprised that it was Gone, Baby, Gone that ultimately Ben filmed and that Alan Ladd wanted to produce. I was a little surprised by that. I was like, you get five books to choose from, and you choose the darkest, and in many ways the least commercial? But I think that speaks to a lie about Hollywood, which is we think that everyone in Hollywood is basically looking for the amusement park ride, this sort of crass, paint-by-numbers script which we’ve all seen a million times, when in fact, in my experience with the films of my books, with the exception of Shutter Island, I’d say they’ve gone for the least commercial, in terms of a film. And it’s really what they’re after is exactly, again the one thing I take credit for that I do well I think is character — that’s what they want. They want things with rich character that they can mine over the course of a two-hour journey. 

Is there a particular novel that you’re surprised hasn’t been picked up?

No, no, I’m not surprised at all. I mean the one I was most surprised at was the one they bought. For years they tried to make The Given Day, and I just kept going, 'Guys, this is never gonna work, you know? It’s 700 frickin’ pages long; I know it’s not gonna work.' And they kept trying, but you can’t make that into a movie. You could make it into a long-form television show, but you can’t make it into a movie.

From your first novel, A Drink Before the War, to your latest novel, World Gone By, you've certainly written your fair share of gangster stories. Why do these shadowy figures continue to interest us?

There’s a couple of things. A, you get to live vicariously through them, which is always fun. But then B, the gangster world is a great metaphor for capitalism, unfettered capitalism. So it’s a great way to look at this sense of, what Don DeLillo did with Underworld — this world that we know exists below us, but we don’t actually see most days. But when we get a glimpse of it, we go, 'Ooh.' And it confirms for us that in some ways, we are all children. The adults are selling us a story that the world works one way, and we’re all like the skeptical pre-teen, starting to go, 'Wait a minute' — and that’s the mob story. Oh, these guys may have assassinated President Kennedy — wow, that’s fascinating, you know? 

Were you a fan of The Sopranos?

Oh, I love The Sopranos. What a great way to do it. I mean, to look at the problems facing all middle-aged white males of a certain middle-management stature in America, and to look at it through the mob. I mean I thought that was brilliant.

James Gandolfini’s last movie role was in your last novel-turned-film The Drop. What did that mean to you?

It meant a lot because I fought for him in that part. That was the only time I’ve ever gone down and dirty with producers. When I heard he was up for the role, it wasn’t like I said, 'Oh, you need to get James Gandolfini. But when they got him, and I said I really want him, and they said, 'Well there’s two other actors in the running,' and I said 'Please, for God’s sake he’s perfect,' I still remember one of the producers saying, 'We’re worried he’s a little too ‘on the nose.’' And I said, 'Sometimes ‘on the nose’ means perfect. So hire him, please, please.' And I wouldn’t say they made the final decision because of me, but I would say that it meant a lot that the writer and co-producer 
was so passionate about that one role. So I was happy.

When you’re engrossed in writing a novel about the underside of life, does it ever weigh you down?

If you’d asked me that question 15 years ago, I would have said that there are no boundaries. But as time has gone on, as I’ve moved on into maturity, I have kids, all sorts of other things, you realize you have to set up a boundary between your work life and your personal life. It might get blurry for a half an hour. I may be deep into a scene, and all of a sudden my daughter may come running down and want to talk to me, and I’m not quite capable of flipping over to having a conversation about Sophia the First or whatever it may be. But in all other respects, yeah, that’s as long as it lasts. Whereas if you’d said, 'What was it like when you were working on Mystic River?', well yeah, that would be days and days, sometimes whole months, in which that was something I was carrying in a different way.

You recently turned 50. Who are you today, compared to a decade ago?

I’m grayer, I’m heavier, I’m also slower, I’m all the shitty things that happen. I’m much happier, though, because I have kids, and that changes everything. That’s a very big thing.

Have your professional aspirations changed in any way over the last decade or so?

Yeah, clearly I live in LA now, so I’m much more ambitious about premium cable television. That’s a world I’ve been in now for about 15 years. And now I’m on a Netflix show called Bloodline. I’m very much looking toward having my
own show. That’s a different ambition than I would have had 10 years ago.

Does that mean you’ve gone Hollywood?

Oh no, if I’d gone Hollywood, I’d be writing The Avengers — you know what I mean?  I’m not doing any of that. I’m just doing my thing in a slightly different medium while simultaneously writing books. 

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