Five essential movies to watch in Boston

The 21st most populous city in the United States, Boston has had an outsized influence on the country’s history. From being a key location in the fight against the British, to an industrial powerhouse, to the home of John F. Kennedy, The Cradle of Liberty has been part of it all.

Today, it has one of the best start-up cultures in the United States outside of the Bay Area, as well as one of the most livable cities. His influence also extended to the world of cinema; especially when it comes to stories of brash masculinity.

It’s logic. People of Irish descent form the largest ethnic group in the city, accounting for 15% of all residents. As a result, many films shot in Boston explore the meaning of Irish American identity in much the same way as New York and Italian Americans. While the Irish historically faced oppression before ascending to the highest positions of power, these films often portray the Irish-American as an unloved outsider, ready to fight against all odds. As an Englishman of Irish descent myself, Boston movies can often seem like some of the most relevant; especially the need for second-generation people to overcompensate somewhat to assert their identity.

From gangster stories to historical dramas to neo-noir thrillers, cinematic portrayals of Boston are filled with moral complexities and fiery performances. We’ve created a list of our five favorites below. Read on to see what we picked.

The dead

Part of the reason The dead is so great is that, like many of Martin Scorsese’s gangster movies, it’s also hilariously funny. A strong Italian-American Catholic, Scorsese manages to locate the essentials of Boston’s Catholic Irish character and exaggerate them to the nth degree. Mark Wahlberg in particular, who would later dwell heavily on Boston’s negative stereotypes in the Ted movies, has a lot of fun playing with the accent.

Wahlberg is part of an all-time cast, which also includes professional jurors Alec Baldwin, Leonardo DiCaprio, Matt Damon, Jack Nicholson and Ray Winstone. Together they play both sides of a war between the Irish mob and the Boston police. Based on the Hong Kong film hellish business, a member of the police infiltrates the mafia and vice versa, making this a deadly game of cat and mouse that is both exhilarating and terrifying.

Goodwill hunting

You can’t talk about Boston without mentioning Ben Affleck and Matt Damon. These speedy friends were both born in the greater city area and have multiple credits between them, either writing, directing, or starring in films set in Boston. Goodwill hunting was the movie that put them on the map. Directed by Gus Van Sant, it’s the story of an unsung mathematical genius who works at MIT as a janitor and spends his free time getting tattoos with his friends.

When he gets into a drunken fight, he is put in therapy, facing Robin Williams, the best of his career. It’s through these conversations that the film really sings; explore the contours of masculinity and what it means to live a meaningful life. It is an essential film of the Irish diaspora: scholars have pointed out that Goodwill hunting perpetuates the sectarian malaise that plagues the whole of the UK and Ireland with the Catholic testament’s distrust of the predominantly Protestant professors at MIT.

Gone baby gone

It’s no surprise that Ben Affleck’s directorial debut is set in his hometown. Gone baby gonebased on the novel by Dennis Lehane, is set in the Dorchester neighborhood and stars his brother Casey Affleck as Patrick Kenzie, a private detective tasked with finding a missing girl.

Boston is seen here as a dark and forbidden city, where the grudges seem endless and probably go all the way back to Letterkenny. Here, Affleck is genuinely interested in exploring every nook and cranny of the city, giving us a full portrait of what this demise means to its people. If Casey Affleck is by far the best actor of the two brothers, as evidenced by his devastating performance in Manchester by the sea party baby party allowed him to really stretch, putting in one of the best performances.

Affleck returned to Boston twice; with a direct thriller The city and historical gangster movie Live the night. He will come back. After all, it’s his house.

Friends of Eddie Coyle

More gangsters never really reach the top. They just carry on with their odd jobs throughout their careers. There’s never really been a better understanding of this than in Peter Yates Friends of Eddie Coyle, starring Robert Mitchum as a shrunken con artist who faces jail time.

The joy of the film lies in the performance of Mitchum, who knows everything, calms down and takes the story into his own hands. We follow him as he faces a strong moral decision between denouncing his friends and upholding his own moral code. The film is a true product of the 70s in its willingness to explore the darker side of mob life.


Much of Irish identity is tied to the Catholic Church. They took their Church with them when they came to Boston, making most of the city’s Irish-Americans Catholics as well. Projector, based on the true story of how the Boston Globe’s “Spotlight” team uncovered widespread and systemic child sexual abuse within the city’s Catholic Church, shows the dark side of a such unshakable confidence in the institutions.

Much of the Irish masculinity never talks about your problems, which is reflected in the residents’ low-key nature when it comes to giving anything to reporters. Projector slowly breaks down these and other hurdles facing journalists through good old-fashioned detective work; showing how powerful it can be to hold the truth in power. Perhaps the most thoughtful Boston film on this list, Projector was a huge hit, winning Best Picture in 2016.

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