If there’s something Dennis Lehane always knew he was good at, it was writing.
What he didn’t always know was that one day, he’d not only make a living out of what was once just a hobby but he would transport some of his stories to the big screen, working with the likes of Martin Scorsese, Clint Eastwood and Ben Affleck.
“Where I grew up, it wasn’t really considered a viable career option, so I took a bunch of different safety majors and realized that I sucked at everything else,” said Lehane, who earned his masters degree at Florida International University. “So when I went to my parents and said ‘I wanna major in creative writing,’ they kind of said: ‘Oh well, you kinda suck at everything else.’”
As of 2023, Lehane has published 15 novels and a short story, five of which have been adapted to the big screen—projects directed by Eastwood, Affleck, and Scorsese.
“Certainly, when Clint Eastwood came along, that was a big deal,” said Lehane. “Not just because he’s such a big name, but because I was a big admirer of all of his films and the way he ran his company.”
The adaptation of Mystic River, his most sold book, received six Academy Award nominations in 2004. It won two, for Best Actor (Sean Penn) and Best Supporting Actor (Tim Robbins). Lehane made a cameo appearance in the film; he is seen briefly waving from a car at the end of the film.
“I knew that whoever would come for it would at least be serious,” said Lehane in an interview for January Magazine in 2001. “Then we got a phone call and it was Clint Eastwood. I was like: ‘Clint Eastwood?’ I mean, come on. And it’s not just because he’s an icon. As a film buff I’ve been following him as a director since Play Misty for Me, his first movie, and I think he’s a fascinating director and I think he’s right for this material.”
While he currently lives in California, Lehane often finds inspiration in Boston, his hometown, when creating new characters and plots for his stories.
“It’s just a fun city, it’s very interesting, very beautiful. It’s a very varied place,” said Lehane. “I don’t know if I’m a total cheerleader for it, I just know that I found it a very interesting place to grow up.”
Despite his attachment to New England, some of Lehane’s formative years unfolded in Florida.
He earned his undergraduate degree from Eckerd College in St. Petersburg in 1988. After a few years of indecision and distress about the future, he followed his roommate to FIU and enrolled in its creative writing graduate program, and received his masters degree in 2001.
“I was kind of ruthless, I was in my mid-twenties, I didn’t know what I was really doing with my life at that point, so I was like ‘I think I’ll hide for another couple of years,’” said Lehane.
The Boston native is very close to current FIU creative writing professors Les Standiford and John Dufresne, who he met during his time at FIU.
“When I met him, he was already a good writer. I like to think I taught him something, but he was already doing pretty good when he showed up,” said Dufresne. “I did direct his thesis, and I and the people in the committee, we liked what he did but I asked him to rewrite one story. It took him two years to do it, and what it became was Mystic River.”
Dufresne also recalls Lehane’s passion for writing, and how he’d often spend his free time working on his craft.
“He and his friends had an apartment up here in Hollywood. Sometimes, I’d go over there with friends, just to hang out and have a beer. He would sit at the kitchen table while the other guys were playing video games and drinking, and write the whole time,” said Dusfresne. “He had the passion for it and the determination, so that’s how he got to where he is.”
But even though he lived in South Florida for a few years, the city never influenced his craft, as he felt he would have just repeated what other writers were doing.
“At that point, Miami was very much a hub for crime writing, which is what I was starting to grow interested in, but a lot of people were doing it,” said Lehane. “I was like, ‘if this many people are working in Miami, the town’s too filled. There’s no space for me.’ So I went the other direction.”
While Lehane has also written for multiple TV shows and movies in the past, he recently dipped his toes into non-fiction with Black Bird, a miniseries based on James Keene’s 2010 autobiography. Keene was a drug dealer who became an undercover operative for law enforcement.
Lehane said writing scripts and books are both rewarding in their own way, but writing novels is much harder.
“With books, it’s only you and the reader, and that’s the only people in that relationship,” said Lehane. “Whereas when you do a film or you do a TV show, there’s 200 people who are weighing in on that interpretation.”
When it comes to producers buying rights to his novels, he’s careful in who he chooses to handle the material.
“You have to divorce yourself from being precious about the material, but I think even more importantly, it’s about who you sell it to,” said Lehane. “I don’t sell to big, large conglomerates, I sell it specifically to producers. You get involved with quality people and then you hope for the best.”
Looking back at his journey, Lehane realizes that writing and chasing his next projects is a big part of finding happiness in life.
“I just want to be running after the next thing—that’s when I’m happiest,” said Lehane.