Known for their rough and tumble neighborhoods, the lived-in authenticity of working-class families, brutes, and often criminals hanging around in the local bar, Boston films operate best when their surroundings and those famous accents for anyone whose wicked smart fill the frames. Novelists like Dennis Lehane (Gone Baby Gone, Mystic River, and Shutter Island) and the playwright Kenneth Lonergan have made films that populate the greater New England area.
At the same time, superstars like Ben Affleck, Matt Damon, and Mark Wahlberg have made it their business to tell stories about their hometowns. Boston films operate in that gray area of being a busy city, but not big enough to hold a candle to the Los Angeles or New York film. Boston has a small-town vibe while still dealing with the sprawl of a modern city.
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10 Fever Pitch
20th Century Fox
The comic guile and brevity of Fever Pitch — a romance set against the Boston city as the Red Sox want on their historic World Series run — are strengthened by its two stars’ charisma and chemistry. Starring Jimmy Fallon (in his only successful turn as a leading man) with the maximum comedic charm of Drew Barrymore, the two go on an unlikely road of love. Hitting all the familiar beats of best friends trying to offer their romantic advice, meeting relatives, and one unusually odd tick that could drive the relationship apart, Fever Pitch is one of the best Beantown comedies. As Fallon plays the dedicated Boston fan whose all-encompassing devotion to a baseball team lands all the jokes it can before finally getting the romance to stick.
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9 The Boondocks Saints
Franchise Pictures
Troy Duffy’s trajectory in Hollywood is another tale of caution and egomania running wild. Crashing and burning before he could ever truly claim success or longevity, The Boondocks Saints will be Duffy’s legacy. Initially bombing at the box office, the film reached cult status after a huge boom in DVD/VHS sales. Made in earnest, the film follows two brothers (Sean Patrick Flanery and Norman Reedus) who take to the Boston streets in a fit of vigilantism to rid the city of criminals and what they deem unnecessary evil. Taking to the random Boston bars and churches emblematic of the Irish Catholicism that runs through the city, Duffy’s film is a relic of the 90s.
8 Mystic River
Warner Bros. Pictures
Adapted from Dennis Lehane’s novel — whose works almost exclusively live in Boston — Mystic River is a tragic, fatalistic look at three lifelong friends intersecting at a deep and brutal crossroads. Directed by Clint Eastwood, whose elemental and patient touch immerses us in the small Boston neighborhoods. Kevin Bacon, Sean Penn, and Tim Robbins play the three friends whose life seemingly marred when Penn’s daughter is murdered. As Penn pulls the most punches in a hammy, electric performance, Eastwood offers no catharsis with his formal restraint. Through trial by error as Penn uses his influence to turn vigilante, Mystic River won Penn and Robbins Oscars for their harrowing, violent performances.
7 The Social Network
Sony Pictures Releasing
Master of the puzzle, director David Fincher took an excellent script from West Wing creator Aaron Sorkin to explore the comeuppance and success of Mark Zuckerberg’s rise to endless wealth. The Social Network spends the first half of the film walking the snowy confines of the Harvard campus and explores the nebbish genius and ego of Facebook’s creator. How his upward climb to billions of dollars also came at the expense of burning bridges with his closest friends and how he ultimately paid out of pocket for damages and lies while still keeping his empire. Jesse Eisenberg does career-best work as the singular-minded psychopath, while Fincher does the unthinkable: making random computer coding seem exciting and tense.
6 Manchester by the Sea
Playwright Kenneth Lonergan makes films that string working-class people together through shattered family dynamics — often through a tragic lens. Manchester By The Sea pries the intimate depths of mundane interactions as broken people attempt to alleviate and deal with the sudden deaths of loved ones. Casey Affleck, who won Best Actor at the Academy Awards, brings his working man, New England cadence to the role of a father who has never been the same since his kids died in a fire. Having to take on new responsibilities after his brother dies, Affleck must wrestle and come to terms with the pain of his tragic circumstances.
5 The Boston Strangler
Based on the real-life serial killer who strangled 13 women in Massachusetts in the early-1960s, The Boston Strangler is directed by Richard Fleischer. The police procedural takes a few liberties with the facts to create a story that shows how ill-equipped the modern police force is to deal with a killer of such magnitude, especially one who sexualizes their violence. Starring a trio of old Hollywood stalwarts — Tony Curtis, George Kennedy, and Henry Fonda — Fleischer puts us almost exclusively in the shoes of the detectives. The police roam Boston with little clues they have to bring evil to justice.
4 The Friends of Eddie Coyle
Paramount Pictures
Based on the novel of the same name, the late Peter Yates directs this part crime caper, heist film, and bad guy hangout with relative ease that never draws attention to itself. Full of colorful Boston banter, The Friends of Eddie Coyle is a mesmerizing exercise in restraint, taking us from dirty pool halls to low-level banks where gun runners supply the criminal food chain. Robert Mitchum stars as Eddie Coyle, a man who’s too smart for his good and unfortunately finds himself, friends, with the wrong people.
3 The Verdict
A grizzled and heroic performance from Paul Newman begins the story of Sidney Lumet’s The Verdict by popping a whiskey double and then combining a beer with a raw egg for breakfast. Newman goes through the mental transformation as a down-and-out lawyer to not only try to win a case of medical malpractice but possibly win back his soul. With a superb second script from playwright David Mamet — something Lumet always had an eye for — creating a resounding, monumental work for legend Paul Newman as he fights in Boston courtrooms. Having to battle the likes of the classic villainy from James Mason, The Verdict finds redemption in the depths of self-loathing.
2 The Departed
Martin Scorsese’s first foray into the depths of the Irish criminal world and taking a step back from his Italian roots, The Departed is an old-school crime epic starring some of the biggest names in Hollywood. Entangled in a web of lies, Scorsese’s film perfectly channels the inner workings of Billy Costigan, played by Leonardo DiCaprio, as he goes toe-to-toe with crime boss Frank Costello. Costello was played to an absolute maximum of sleaziness by icon Jack Nicholson (who, surprisingly, has only worked with Scorsese this one time). The Departed would go on to win Scorsese his first Oscars for Best Director and Best Picture despite its grit and ruthlessness.
1 Good Will Hunting
Miramax Films
The ultimate Boston film that made everyone unfamiliar with the Northeastern city think of the Southie neighborhoods where the titular character lives, Good Will Hunting catapulted Ben Affleck and Matt Damon to Hollywood darlings. Finally realizing their dream script to the big screen — a long journey that had everyone from Michael Mann and Steven Spielberg attached to direct — the duo finally landed Gus Van Sant. The director imbues the films with a wonderful autumn palette, warmth, and a few slow-motion, impressionistic scenes right in line with the director’s aesthetic. But a show-stopping role for Robin Williams as the wounded psychologist offers Will a window into his soul. Both hailing from the same neighborhood the two form a bond deeper than friendship.
