An author who’s been active since the 1990s, Dennis Lehane tends to write fairly dark books that belong to the crime and/or mystery genres. There’s a style to them that makes most well-suited to film adaptations, with a fair few high-profile directors having tackled and adapted Lehane’s work since the start of the 2000s. He’s also branched out into screenwriting, particularly in the world of television, being credited with writing a few episodes of The Wire (a hell of a thing to have on your CV, so to speak), and then he also played a role in writing some Stephen King TV adaptations, including the Mr. Mercedes series and The Outsider miniseries.

But below, there’s a focus just on the movies that were made based on stories he’d written, with four being from novels, and one being from a short story he wrote (and with that one, he also ended up writing the adapted screenplay). Of these films to date, there’s only one that kind of misses the mark, while the others range from pretty good to pretty great, which is a good track record, and does suggest his work is pretty adaptable. Compare it to the absolutely chaotic run of movies based on stories by the aforementioned Stephen King, for example. Okay, maybe not a fair comparison, considering King’s a bit of a quantity-over-quality writer at times, and some of his work isn’t well-suited to the small or big screen, but still…

5

‘Live by Night’ (2016)

About a decade on from his first successful attempt at adapting a Dennis Lehane story to the big screen (more on it in a bit), Ben Affleck gave the whole endeavor another shot with 2016’s Live by Night, and the results weren’t nearly as good. In fact, this is probably the only truly disappointing movie adapted from a Lehane novel or short story, and it frustrates because all the pieces were in place. Live by Night has an intriguing enough premise, since it’s about Boston gangsters trying to make a living during the Prohibition era, running into various obstacles and adversaries, and also, it’s got a pretty great cast. Ben Affleck had directed actually good movies well before this, and stars here, alongside the likes of Elle Fanning, Brendan Gleeson, Sienna Miller, Zoe Saldaña, Chris Cooper, and Titus Welliver.

Everyone there has been in good stuff before, but no one manages to do anything near career-best work in Live by Night. It feels like the kind of story – genre and setting-wise – that Affleck should be able to make work, as a director (based on what he’d directed before), but nothing coalesces or feels right here. Some might call Live by Night a little overlooked or underrated, but those people are probably being a bit generous or soft on the whole thing. A movie like this doesn’t have to be exciting, but it should at least be more interesting than this. Live by Night looks good, and might sound good on paper, but watching it makes for a real slog of a viewing experience. It’s not really worth it, and feels so much longer than you’d expect a movie with a 129-minute runtime to feel.

4

‘The Drop’ (2014)

Image via Searchlight Pictures

Things get a bit confusing with The Drop, because this 2014 film was based on a short story by Dennis Lehane called “Animal Rescue,” and Lehane himself wrote the screenplay himself, and then a novelization of the movie also called The Drop, which came out the same year as the movie. It’s an unusual series of events when it comes to adaptations and novels and all that, but that’s breaking it down as succinctly as possible. Anyway, the actual story here plays out like a pretty low-key crime/drama one, being about various desperate people trying to get by in a small neighborhood, and how a robbery gone wrong ends up affecting various people who are already facing hardships. James Gandolfini is one of the stars here (and it was his final film role), but you probably shouldn’t go into The Drop expecting anything too gangster-heavy.

It does explore crime to some extent, but The Drop is also fairly slow-paced and character-focused, perhaps as a result of not having a ton of material to work with, owing to that original short story being, you know, short. But Gandolfini is good, as is the almost always reliable Tom Hardy, and most aspects of the film beyond the performances are decent, and that’s maybe enough. It’s certainly a step-up quality-wise from something like Live by Night, but it’s also hard to imagine too many people being really blown away or super impressed by it. Bada bing, bada boom, it’s alright, capiche? Fuggedaboutit.

3

‘Shutter Island’ (2010)

Image via Paramount Pictures

So, Shutter Island has a good twist. It’s got that going for it above anything else, but it’s also hard to talk about the movie without giving away what it ends up being about. Similarly, there’s not much about it that’s amazing beyond the way it messes with your mind, so that makes it even more difficult to talk about. Hmm. Well, it begins in a simple way, with two U.S. Marshals heading toward a small island that has an isolated psychiatric facility on it. There’s an inmate there who’s gone missing, and the pair need to work out what happened, and everyone there is either eccentric or seems to be hiding something, or a bit of both. So the simple mission gets complicated, and then further complications are revealed when it comes to the dark history of one of the Marshals and his personal life.

Maybe the most interesting thing about Shutter Island, besides the twist, is the fact that it was directed by Martin Scorsese and stands apart quite a bit from his other films. He’d tackled psychological dramas and thrillers before, to some extent, but not in the way done in Shutter Island, with Dennis Lehane’s style kind of out of step with most source material that seems suited to Scorsese’s sensibilities. Still, it was a moderately successful movie financially, and Shutter Island does also have its supporters, so hopefully, this won’t be read as picking on the film or trying to beat it while it’s down or anything. It is a mostly pretty good psychological thriller/mystery movie with one very effective twist/revelation up its sleeve, and it’s certainly worth at least one watch for that alone.

2

‘Gone Baby Gone’ (2007)

Image via Miramax

Gone Baby Gone was based on the fourth book in the six-part Kenzie & Gennaro series, but works as a standalone movie pretty well (also, the book’s title was technically a little different: “Gone, Baby, Gone”). The story here initially concerns the disappearance of a young girl, following the two private detectives who are tasked with finding her, as they’re hired by the family of the girl who don’t believe the police are up to the task of carrying out the search properly. As you might expect, things get a good deal more complicated from there, and everything balloons to the point where it’s no longer “just” about the search for a missing child.

It’s a familiar-sounding plot for a crime/mystery story to follow, sure, but it goes to more interesting places morally (and does some clever stuff casting-wise, too). Also, Gone Baby Gone was an impressive directorial debut for Ben Affleck, too, who directed his younger brother, Casey Affleck, here, in the lead role. It more than gets the job done, and could well be one of the more underrated films of its genre from the 2000s, since you don’t hear a ton of people talking about it anymore, but maybe they should. It’s good.

1

‘Mystic River’ (2003)

Image via Warner Bros.

The first movie to be based on a Dennis Lehane novel was 2003’s Mystic River, which is also, to date, the best of any films that adapted source material by the author. It’s a grim story both on page and on the big screen, being about three adult men who were once childhood friends, and the sorts of hardships that come about after one of them goes through an unspeakably awful tragedy. There is a hunt for justice in the wake of what happens, and along the way, various past tragedies and misfortunes are explored, and the misery just compounds. Like, it is a great movie, and very well-made (not to mention powerfully acted), but it’s also a huge bummer, made at a time in Clint Eastwood’s directing career when he seemed particularly willing to explore and depict emotionally upsetting stories (see also Million Dollar Baby and Letters from Iwo Jima).

Mystic River is kind of a crime movie, but it shines brighter as a drama, what with how in-depth it gets with its characters and what the narrative ends up putting them through. You get enough by way of mystery and a bit of a police procedural thing going on to keep it all narratively interesting, but it arguably ends up working better as a character study and an exploration of how past tragedies can worsen present-day ones. So, don’t put it on if you want a movie that’ll give you a good/fun/wholesome time, but if you’re up for something heavy, Mystic River is potentially one of the heaviest mainstream American releases of its decade.

Mystic River

Release Date

October 15, 2003

Runtime

138 minutes

Writers

Brian Helgeland, Dennis Lehane