10 Best Boston Crime Movies

Summary

• The Boston movie subgenre emerged from a crime wave, gang wars, and government corruption, fostering a gritty, brooding tone.
• The genre is flexible, allowing for thrillers, dramas, and neo-noir, with Oscar contenders like “Mystic River” and “The Departed.”
• Some iconic entries in the genre include “The Friends of Eddie Coyle,” “Gone Baby Gone,” and “The Town,” known for their compelling narratives.

Since the 1970s, “the Boston movie” has become its own cultural institution. Spurred by a sudden crime wave, a series of gang wars, and rampant government corruption in the Bay State, this loose subgenre has coalesced over the past half-century into something familiar. By the end of the 2000s, the Boston movie became associated with a particular tone (gritty, brooding), set of themes (the ties that bind, disillusionment) and cast of characters–– often including ensembles pairing Matt Damon and Ben Affleck some combination of Afflecks (Casey or Ben) and Wahlbergs (usually Mark, whose best roles are often in Boston movies).

The Boston movie is also fundamentally an off-shoot of the crime film (though the eminently quotable Good Will Hunting is the exception that proves the rule). Despite all the Boston movies’ familiar conventions, though, the genre mold has proven surprisingly flexible. The Boston movie has delivered numerous highly successful Oscar contenders and allowed directors a compelling sandbox for thrillers, dramas, and even neo-noir, as well as more familiar takes on the police procedural.

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10 The Boondock Saints (1999)

Directed By Troy Duffy

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The Boondock Saints 1.0

After brothers Connor and Murphy kill two Russian mobsters in self-defense, they set out on a vigilante mission to rid Boston of crime and violence. However, an FBI agent is hot on their trail.

A classic of the genre, the story behind The Boondock Saints is just as quintessentially New England as the final product itself. Hartford-native and aspiring metal musician Troy Duffy wrote the script for The Boondock Saints while he was tending bar in LA. According to the making-of documentary, Overnight, which chronicles the myriad of small-scale disasters the production faced, Duffy was able to get the attention of Harvey Weinstein, whose production company (briefly) financed the film.

This gloriously over-the-top crime thriller about two Irish brothers turning vigilantes after getting fed up with the world’s cruelty is chock-full of guns, one-liners, and five o’clock shadow. It also features a fantastic Willem Dafoe as a gay detective with a twinkle in his eye and opera on his stereo. This one may not be Oscars material, but it’s a certified Boston classic.

9 The Thomas Crown Affair (1968)

Directed By Norman Jewison

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The Thomas Crown Affair (1968)

The Thomas Crown Affair is a 1968 heist film directed by Norman Jewison, featuring Steve McQueen as a wealthy businessman who masterminds a bank heist. Faye Dunaway stars as an insurance investigator who aims to bring him to justice. The film is known for its stylish direction and innovative use of split-screen visuals, underscored by Michel Legrand’s memorable score, including the Oscar-winning song “The Windmills of Your Mind.”

While many readers may be more familiar with the remake of The Thomas Crown Affair, set in New York City, the original film was set in Boston high society. This slick heist movie stars movie star Steve McQueen as a bored genius who conspires to steal millions from a bank for the thrill of it.

Unlike many other Boston movies, this one takes its cues from Hitchcock and James Bond rather than John Cassavetes and Paul Schrader. It’s more aligned with contemporaries like The Italian Job than it is with the gruffer, rough-and-tumble New Hollywood offerings on the horizon, a la Mikey and Nicky. Still, under its dapper exteriors and Rope-esque stylings, it’s a Boston movie, through and through.

8 The Boston Strangler (2023)

Directed By Matt Ruskin

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The Boston Strangler Director Richard Fleischer Release Date October 8, 1968 Cast Tony Curtis , Henry Fonda , George Kennedy , Mike Kellin , Hurd Hatfield , Murray Hamilton

The Boston Strangler is set within the exact context that eventually birthed the Boston movie as a subgenre. While infamous Irish mobster Whitey Bulger was controlling the streets, Albert DeSalvo, the Boston Strangler, was stalking them, brutally murdering thirteen women in the city between 1962 and 1964.

The movie that takes his moniker for its title is unique among the Boston crime subgenre for its feminist perspective on this oft-documented, long-unsolved case: It follows two real-life Boston Strangler investigative reporters, Loretta (Keira Knightley) and Jean (Carrie Coon), as they try to trace the killer. Where most films in the genre feature only peripheral female characters (typically mothers, wives, and girlfriends), here the two women’s struggles with sexism in the workplace are layered and resonant with a tragic rash of femicide.

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7 Mystic River (2003)

Directed By Clint Eastwood

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Mystic River Director Clint Eastwood Release Date October 15, 2003 Cast Sean Penn , Tim Robbins , Kevin Bacon , Laurence Fishburne , Marcia Gay Harden , Laura Linney

Like The Boston Strangler, Mystic River is an investigative film. This neo-noir, directed by Clint Eastwood, was nominated for six Oscars, including Best Picture, when it was released in 2003, and is one of the pillars of the Boston movie genre. Beginning with a haunting cold-open depicting the abduction and sexual abuse of Dave (Tim Robbins) in mid-1970s Charlestown, the film contends with his trauma in the present, exacerbated by the murder of his friend Jimmy’s daughter, Katie (Emmie Rossum).

While narratively the film centers on the stories of its men (Kevin Bacon, Sean Penn, and Tim Robbins), in a certain sense, the film’s heart lies with the women most impacted by their trauma, making it a narrative precursor to a film like The Boston Strangler. For this and other reasons, this somber take on the Boston movie is deeply moving.

6 The Friends of Eddie Coyle (1973)

Directed By Peter Yates

The Friends of Eddie Coyle (1973)

An aging hood is about to go back to prison. Hoping to escape his fate, he supplies information on stolen guns to the feds, while simultaneously supplying arms to his bank robbing chums.

Director Peter Yates Release Date June 26, 1973 Cast Robert Mitchum , Peter Boyle , Richard Jordan , Steven Keats , Alex Rocco , Joe Santos , Mitchell Ryan , Peter MacLean

The Friends of Eddie Coyle is arguably the first Boston movie as that designation is currently understood. It tells the story of aging, desperate, hangdog Eddie “Knuckles” Coyle (Robert Mitchum) as he tries to work his way out of a jam with the FBI and debates selling out his contacts in the bank robbing business.

Set almost contemporaneously with The Thomas Crown Affair, this film’s varied location shooting and cast of naturalistic character actors make it a poignant portrait of a city in the midst of a financial decline. Its characters are defined by their loneliness and the precarity of their ties to their communities, torn apart by the dual incentives of love and money (and the long arm of the law). Though it flopped at the time of its release in 1973, it has since been credited for its contribution to the genre as well as its nuances, its performances, and its style.

5 Gone Baby Gone (2007)

Directed By Ben Affleck

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Gone Baby Gone 4.5

Gone Baby Gone is a crime drama centering on a detective investigating the disappearance a little girl. But soon after he begins digging for the truth, he is victim to a personal and professional crisis.

Director Ben Affleck Release Date October 19, 2007 Cast Casey Affleck , Michelle Monaghan , Morgan Freeman , Ed Harris , Amy Ryan , Amy Madigan , Titus Welliver

Gone Baby Gone is another classic of the Boston film subgenre that had already flourished in the years prior to this, Ben Affleck’s directorial debut. This hardscrabble tale of desperate characters and broken families shares a significant amount of DNA with Mystic River. Here, a couple (Casey Affleck and Michelle Monahan) work to find their abducted four-year-old daughter, uncovering a web of criminal connections, drugs, and despondency in their tough neighborhood. Its razor-wire tension and grim portrayal of marriages tested and children taken is harrowing.

At the same time, Affleck’s debut can also be identified as the beginning of the end of the Boston movie boom–– or at last the beginning of the backlash to its “grittiest” impulses. As Patrick Radden Keefe put it in a takedown of the film’s perceived excesses in Slate,“For much of the movie, half of Dorchester seems to be standing around outside their creaky wooden houses, just killing time…[Gone Baby Gone] is not so much what Mean Streets did for New York as what Deliverance did for Appalachia.”

4 The Town (2010)

Directed By Ben Affleck

The Town 4.5

Directed by and starring Ben Affleck, The Town is a crime thriller detailing a robber developing romantic feelings for one of his victims after a robbery takes place. As these complicated feelings develop, the team makes plans to Rob Fenway Park. Aside from Ben Affleck, Rebecca Hall, Jon Hamm, Blake Lively, and Jeremy Renner also star in the movie.

Director Ben Affleck Release Date September 17, 2010 Cast Rebecca Hall , Ben Affleck , Blake Lively , Chris Cooper , Jon Hamm , Jeremy Renner

That kind of criticism didn’t stop Affleck from achieving a second critically and commercially triumphant Boston movie in 2010, with The Town. One of the most enduring and iconic entries into the genre, the film stars Affleck himself as a Dorchester boy who gets embroiled in a bank heist by his hotheaded friend Jem (Jeremy Renner). Things really get complicated when he falls in love with the women they took hostage and then released.

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While The Town shares many of the same themes as Affleck’s debut, Gone Baby Gone, it adopts a lighter tone and touch with its bank-heist-thriller-cum-romance plot line. Because of this, the film has a winning, highly rewatchable quality that other, grimmer films in the genre sometimes lack.

3 Spotlight (2015)

Directed By Tom McCarthy

Spotlight 4.0

Based on a true story, Spotlight is a drama film that tells the story of reporters who are privy to terrible details about goings on within the Roman Catholic Church. When several allegations are levied against the church, the Boston Globe sends out a team of reporters to investigate John Geoghan, who was accused of molesting several children. Believing there is a cover-up, the team goes to incredible lengths to find the truth and prove the guilt and complicity of both John and the church.

Director Tom McCarthy Release Date November 25, 2015 Cast John Slattery , Rachel McAdams , Michael Keaton , Jamey Sheridan , Stanley Tucci , Billy Crudup , Brian D’Arcy James , Mark Ruffalo , Liev Schreiber

Spotlight, which won Best Picture, is less of a crime drama and more of a procedural thriller in the style of All the President’s Men. The film is based on the true story of The Boston Globe spotlight team’s investigation of child abuse in the Catholic Church’s Boston diocese.

Spotlight is far less violent than films like The Town, and far less graphic than films like Mystic River, making it more narratively conventional. Nevertheless, even on this more subdued aesthetic register, its twists and turns are understandably agonizing in their enormous implications for faith, power, and politics.

2 Shutter Island (2010)

Directed By Martin Scorsese

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Shutter Island 3.5

Martin Scorsese’s Shutter Island is based on the novel of the same name by Dennis Lehane and stars Leonardo DiCaprio, Mark Ruffalo, and Ben Kingsley. Set in 1959, Shutter Island follows two U.S. Marshalls – Teddy Daniels (DiCaprio) and Chuck Aule (Ruffalo) as they are sent to investigate the disappearance of a patient from a hospital specializing in psychiatric care.

Director Martin Scorsese Release Date February 19, 2010 Cast Leonardo DiCaprio , Emily Mortimer , Mark Ruffalo , Ben Kingsley , Max Von Sydow , Michelle Williams , Patricia Clarkson , Jackie Earle Haley

Shutter Island is rarely recognized as a Boston movie in the proper sense. This twisting psychological thriller, directed by Martin Scorsese, is nevertheless fundamentally tied to other films in the genre from its inception: It’s based on a novel by Dennis LeHane, who also wrote Gone Baby Gone, Mystic River, and Live By Night (a Boston crime thriller set in the 1920s that Ben Affleck adapted in 2016).

Shot in Southeastern Massachusetts, the film is set on an island in Boston Harbor where a detective (Mark Ruffalo) is sent to investigate the disappearance of a fellow police officer. The film is satisfyingly mind-bending, and its star, Leonardo DiCaprio, is drawing on the same kind of style he employed in Inception that same year. This film’s ambitious scale, complex plot, and hallucinatory style make it highly unique among Boston movies.

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1 The Departed (2006)

Directed By Martin Scorsese

The Departed 4.5

A remake of the 2002 film Infernal Affairs, Martin Scorcese’s The Departed is one of the definitive crime epics. It follows Colin Sullivan (Matt Damon), a Massachusetts State Police officer who serves as an informant for mob boss Frank Costello (Jack Nicholson), and Billy Costigan (Leonardo DiCaprio), an undercover cop placed within Costello’s organization. Both Sullivan and Costigan scramble to uncover the other’s identity in order to save their own lives from the wrath of Costello and his gang.

Director Martin Scorsese Release Date October 6, 2006 Cast Martin Sheen , Matt Damon , Jack Nicholson , Mark Wahlberg , Leonardo DiCaprio

The Boston movie wouldn’t be the same without Martin Scorsese’s triumphant, ribald, hard-boiled classic The Departed. The film is most unanimously considered the peak of the subgenre and won Best Picture and Best Director in 2006.

The Departed
is eminently rewatchable and compulsively entertaining

Inspired by the life of mobster Whitey Bulger, the film is a winding tale of cops and robbers and honor among thieves. The lives of police detectives, politicians, and petty criminals overlap and blur in Whitey’s orbit, destroying lives, loves, and reputations in the process. The Departed features one of Jack Nicholson’s most iconic performances as Bulger, and makes compelling use of many of the subgenre’s mainstays, including Damon and Mark Wahlberg, whose performance is particularly memorable. Like The Town, The Departed is eminently rewatchable and compulsively entertaining, combining Scorsese’s masterful style with the narrative structure of a particularly good crime novel.

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