04/13/2011 10:12 am ET Updated Dec 06, 2017

Dennis Lehane on Good and Evil in Literature

The author of nine novels including New York Times bestsellers Gone, Baby, Gone; Mystic River; Shutter Island; and The Given Day, Dennis Lehane -- more difficult to track down than Madonna, according to his own publicist -- appeared at his own high school in South Boston today to talk to students about how he became a writer and the moral ambiguity of his characters and the world.

"No one in Dorchester had ever become a writer when I was here in the early '80s," Lehane told the boys. "All we had was Donna Summer, and she tried to say she was from Roxbury to give her more street cred. We weren't about to claim a disco star as our own."

Lehane credited a nun who gave him his first library card and two priests who first showed interest in his writing at Boston College High. But still he wasn't sure. He dropped out of Emerson College and then UMass Boston before coming to the conclusion at 19 that "I suck at everything except writing."

The key to his success has been his "hyper-focus," he said. "I had total focus from that point on because there was no safety net. If I failed I was going to have to go back to driving a cab." Until the publication of his fifth book, his father would routinely call Lehane every time Boston Gas was hiring to tell him to apply for a real job. When Clint Eastwood bought the rights to Mystic River, Lehane called his parents to tell them the news. His dad's response, in all seriousness, was "Who is that?"

Lehane still lived like a college student, with two roommates and a beater car, well into his late 20s. He had realized that he was attracted to tragedy, characters, and stories that took him down dark paths. "For me, the story is the vehicle by which the characters' inner life, their soul, is shown. Plot always comes last."

In terms of process, Lehane was at a loss to explain how he actually writes. He often stares at the ceiling, he says, hoping for inspiration. He likes to write in the morning, "hopefully still in a dream state since my dreams often give me a clue," for two or sometimes three hours. But "after three hours, it's all crap and I'm going to have to re-write it anyway."

He finally knew he might actually have a writing career when his fourth book, Gone Baby Gone, became a modest hit. President Clinton was photographed carrying the book off Air Force One, and Stephen King devoted the first paragraph of a NYT review that was supposed to be about Harry Potter to Lehane. And eventually his dad noticed that the biggest billboard in Boston was advertising his son's book.


Lehane made clear that all his books are morally ambiguous on purpose. "Gone, Baby, Gone is about what happens when a child is abducted but the place that child ends up is better than where she started, and Mystic River is about the myth of that guy who sets the wrongs of society straight, only in this case he kills the wrong guy. I was trained by Jesuits. Everything must be questioned, considered. There is no fundamental knowledge. You have to turn over every rock for yourself. You don't sleep well after the tough decisions. Welcome to adulthood. At the end of Gone Baby Gone the lead character is right and he is wrong. There is no easy answer."

The fascination with ambiguous morality placed in a harsh urban setting is what attracted Lehane to write for The Wire. "In Baltimore you have a better chance as an African-American male to die by the time you are 20 than to live. Only one in four middle schoolers make it out. We made no moral judgment about what anyone does to survive. I don't see a world of good and bad people, saints and sinners. People are people and if you put them in particular situations you will be surprised. Therein lies the story."

He is currently at work on a new book set during Prohibition in Boston, Tampa, and Havana. "My worst books were easiest to write," he told the students. "The best were all murder to write. The things that take the most work--pulling something of depth out of yourself--are the most valuable."

Read more from The Good Men Project here.

Photos: Flickr/AlcoholicaMan,