5 Thrilling Dennis Lehane Adaptations

Twenty-five years ago, a strange car pulled into the neighborhood of three boys—Sean Devine, Jimmy Markum, and Dave Boyle. One got in the car, but all three of their lives were forever changed. Now, Sean is a homicide detective assigned to the murder investigation of Jimmy’s daughter. And then there’s Dave, who came home the night Jimmy’s daughter was killed covered in someone else’s blood.

In 2003, Clint Eastwood directed, scored, and co-produced the adaptation starring Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Laura Linney, and Marcia Gay Haydon. The all-star cast combined with Eastwood’s directing gained six Academy Award nominations, with Penn and Robbins winning Best Actor and Best Supporting Actor, respectively. In total, Mystic River was nominated for 56 awards, taking home wins for 24 worldwide.

The biggest difference between the novel and the adaptation is that the movie is far more of a murder mystery than the dark, psychological character study of the book. While all of these elements are present in both works, the tragedy and nuance of how trauma deeply influences every decision of the characters is far more defined in the book. Lehane wasn’t directly involved in the adaptation of Mystic River but did acknowledge he was comfortable with Eastwood’s directing style and story-telling abilities to give his characters the time and care he felt they needed on the big screen. He even makes an appearance, briefly waving from a car in the garage at the end of the film.

The fourth novel in the Kenzie & Gennaro series, Gone, Baby, Gone, follows Patrick Kenzie and Angela Gennaro as they are hired to investigate a missing four-year-old girl.

Amanda McCready was taken from her bed on a warm summer night. While her aunt and uncle are loving caregivers, her mother is a drug addict with dangerous friends. The case garners immense media attention, but Kenzie and Gennaro simply can’t make ground in finding the little girl. What they do find is a dark underworld filled with depraved criminals capable of perpetrating horrendous acts against the innocent. As summer fades, evidence of Amanda’s abduction—and life—fades with it. But then another child goes missing.

The adaptation was Ben Affleck’s directorial debut, and he also co-wrote the screenplay with Aaron Stockard (The Town, The Talented Mr. Ripley). It stars Casey Affleck and Michelle Monaghan as the lead investigators, with a stellar supporting cast including Ed Harris, Morgan Freeman, John Ashton, Amy Ryan, and Titus Welliver.

The movie was originally set to be released in December 2007 in the UK, but was postponed when Madeleine McCann went missing, and the Malaysian release was delayed from September 2007 to March 2008 when eight-year-old Nurin Jazlin was kidnapped and later found murdered. Given the dark and disturbing themes explored in the film, producers decided that elements of the actual crimes were hauntingly close to events in the film and chose to delay release accordingly.

In 2018, Fox ordered a pilot to remake the film into a potentially longer series that was intended to expand into the entire series. The series was set to star Joseph Morgan and Peyton List. Unfortunately, Fox passed on the pilot in May 2018.

A storm traps U.S. Marshal Teddy Daniels and his new partner Chuck Aule on Shutter Island, where they’re investigating the disappearance of a patient from Ashecliffe Hospital for the Criminally Insane. Somehow, Rachel Solando escaped her cell and is somewhere on the island. As Daniels and Aule investigate, they discover whispers of experimental psychiatry and sinister surgeries are being done to the patients. Haunted by nightmares and migraines, Daniels starts to lose himself to the conspiracies. Or is he discovering who he is, after all?

The movie rights to Shutter Island were initially acquired by Columbia Pictures in 2003. When production never progressed, the rights reverted back to Lehane, who then sold them to Phoenix Pictures where director Martin Scorsese and Leonardo DiCaprio took interest in the film. Though critics felt Shutter Island wasn’t Scorsese’s best work, the movie was his second highest-grossing film, bringing in nearly $300 million worldwide.

One interesting change between the movie and the novel is the ending line. Teddy asks Chuck if it would be worse “to live as a monster, or to die as a good man?”. The line wasn’t in the novel, and Scorsese worked with a psychiatric advisor to craft the line within the context of Teddy’s state of mind. Many people have discussed what that line means, and Lehane himself has weighed in, stating “it’s just one moment of sanity mixed in the midst of all the other delusions.”

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For a while, there was a prequel in the initial planning stages at HBO with Scorsese directing, and screenwriter Tom Bernardo returning to the island to co-write with Lehane. It seems production has moved slowly and little news has come from the project since it was first announced in 2014, but it appears to still be in development as of August 2021.

Adapted from the short story “Animal Rescue”, The Drop follows barman Bob Saginowski (Tom Hardy) after he gets robbed working in a mafia-run bar. Looking for a reason to live, he finds an abandoned pit bull in a trash can. After the robbery, Saginowski ends up getting dragged into an investigation that starts putting pressure on the local mob and pushes several neighborhood thugs past the point of desperation.

Like all of Lehane’s stories, the complicated threads of relationships and the consequences of choices are prominent themes in this gritty crime drama. He wrote the screenplay and Michaël Roskam directed. James Gandolfini also starred in the film, and it ended up being his final on-screen role before the actor passed away in 2013.

As an interesting turn of events, The Drop was adapted back into a longer novel and released in September 2014, just days before the movie premiered. This was the first novel that Lehane wrote the screenplay first and then sold to Hollywood, rather than writing the book to sell the movie rights after publication. It was also Lehane’s first written film screenplay. 

It’s 1926 and Boston is in the height of prohibition. Illegal liquor flows in the streets, gangster bullets fly through the city, and Joe Coughlin is determined to make his mark. The son of a prominent police Captain, Joe works his way through the criminal ranks. But a life of crime has a steep price. One that Joe may not be willing to pay.

Live by Night was directed, written, and produced by Ben Affleck, who also starred in the film with Zoe Saldana, Elle Fanning, Brendan Gleeson, Chris Cooper, Sienna Miller, and Chris Messina. Despite the star-studded cast, the movie ended up releasing to mixed reviews and lost a devastating $75 million.

The rights were initially purchased by Warner Bros. in April 2012 with Leonardo DiCaprio set to star and develop the movie through his new company, Appian Way Productions. For unknown reasons, in October of the same year, Affleck was announced as writer, director, and star of the film, with his own production company, Pearl Street Films. DiCaprio’s Appian Way Productions stayed on as co-producer.