Following ‘The Outsider’ finale, Dennis Lehane comes to Aspen Winter Words

Andrew Travers
The Aspen Times
Novelist and screenwriter Dennis Lehane will speak Tuesday at the Winter Words author series.
Gaby Gerster/Courtesy photo

EDITOR’S NOTE: On Monday morning, Aspen Words announced it had canceled Dennis Lehane’s Winter Words event scheduled for Tuesday, March 10, 2020.

Novelist Dennis Lehane also has been a bard of the prestige TV era, from its beginnings on “The Wire” to its latest entry, “The Outsider,” which had its finale Sunday night on HBO.

A master of the literary thriller, Lehane — who will give a talk on his life and work at the Winter Word author series Tuesday — is one of a handful of crime writers who ushered in the Peak TV era. Alongside authors like Richard Price and George Pelecanos, he’s been the bridge between the period when novels remained at the center of the popular culture and the prestige television era, when America’s proverbial watercooler conversation shifted from the bestseller list to premium cable.

“If I was seeing ‘Breaking Bad’ when I was 20, would I say, ‘Oh, I gotta move to LA?’ Probably,” he said in a recent phone interview from his home in Los Angeles.

But Lehane, 54, who first broke out with Boston-based whonunits in the 1990s, still believes in the novel. He’s writing one now, alongside his screenwriting work.

“The book I’m writing now is different than anything I’ve written before,” he said. “Though it exists in the world I usually stay in with the Irish political machine in a parochial neighborhood and the very tribal world of cops. So it has enough of the DNA, but it’s going very slowly, and I’m actually enjoying it.”

He estimates he’s writing about a page per week — while also working on several television projects for HBO, unsure of which will make it into production next.

Lehane broke out in the 1990s with his Kenzie-Gennaro private-eye series — the best-known of which is “Gone Baby Gone,” also the first of many to be adapted into a film — about a streetwise couple working cases in his native Boston. 

His first five books poured out of him effortlessly, he recalled. But the next five were “torturous.”

“I found writing novels grew increasingly more difficult as I did it, not less,” he explained. “I started thinking, ‘Oh my god, I may have a finite number in me.’ … It’s still the best job in the world. It still beats the hell out of selling shoes, but it was getting progressively harder to do for me.”

The pace of prose slowed as he finished his initial burst of Kenzie-Gennaro novels from 1994 to 1999, and coincided with the early days of the prestige TV era.

David Simon and Edward Burns recruited Lehane to join the writing team for “The Wire.” His contributions would include writing the death episode of fan-favorite street tough Omar.

Following the Kenzie-Gennaro mysteries, he began playing with genre in his novels — subverting and exploiting the reader’s expectations of a given form. He turned to tragedy for “Mystic River,” to gothic horror for “Shutter Island.” He played with the Doctorow-styled historical epic in a trilogy that concluded with 2015’s “World Gone By.” And, most recently, he tried his hand at Hitchcockian thriller for 2017’s “Since We Fell.”

“Since We Fell” does ramp up into the twisty and violent territory readers expect from Lehane, but the first 100 pages or so are mostly a character study of Rachel Childs, a woman rising in the ranks of Boston TV news while also searching for the father she never knew.

Between the novels, he’s worked on TV shows like “Boardwalk Empire,” “Mr. Mercedes” and “The Outsider,” and wrote the screenplay for “The Drop.”

“I leaned into writing for television a little more than I might have if (novels) were still coming out easily,” he said.

Working in television writers’ rooms, he believes, has led him to tighter plotting in his novels.

“Plot is the last thing I bring to the party when I’m writing a book,” he said. “I’m always just wandering around with characters. Writing for television is the exact opposite. You are constantly trying to advance the story, which is in service of the character.”

But his novels have never been about the empty thrills of a well-plotted page-turner. His characters, from the imperfect couple at the heart of the Kenzie-Gennaro books to the tortured agoraphobic in “Since We Fell,” are complex humans facing awful moral quandaries and bad options. The books are full of dirty cops and children in peril and adults in crisis, but his true subject throughout has been morality. The first of his two “Outsider” episodes — working with Richard Price to adapt a novel by Stephen King — includes a classic Lehane scene: a long, tense and talky car ride where a morally conflicted bad guy and a morally conflicted detective subtly work out what each of them must do to save or destroy the other.

His subjects are unerringly dark and grim, but leavened frequently with welcome splashes of wit and humor. It is no wonder that the film adaptations have drawn some of the best actors of our time and led to some of the most indelible performances by Leonardo DiCaprio, Sean Penn, Tim Robbins, Casey Affleck and James Gandolfini.

He’s taken a hands-off approach to the film adaptations of his novels, staying away from the sets and letting directors, screenwriters and actors do their work. But he has committed to only work with the best. It’s been an astounding run, seeing his books adapted for the screen by Academy Award winners Clint Eastwood (“Mystic River”), Ben Affleck (“Gone Baby Gone” and “Live By Night”) and Martin Scorsese (“Shutter Island”).

“That’s not luck,” he said. “It’s absolutely by design. … I only work for premium cable and I work in prestige TV, and when I work in film I work with really good people.”

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