Planning Magazine

Take a Cinematic Tour of Boston

The movies that put Boston's planning and people on the big (and little) screen.

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In one of Good Will Hunting's most iconic scenes, Robin Williams gives Matt Damon's character a heart-to-heart in Boston Public Garden, a 24-acre, nearly 200-year-old park in the city's downtown. When Williams passed away in 2014, the park bench they sat on became a public memorial. Photo courtesy of Miramax.

While APA's National Planning Conference might not be in Boston as originally planned this May, it's still possible to remotely explore The Athens of America, The City on a Hill, The Hub of the Universe — or, more frequently, the original underdog gritty-city, where you pahk ya cah, grab some chowdah, and take a walk down by that dirty water. (Given that I live in Boston, you'll observe that real Bostonians never call it "Beantown" — that nickname only exists so we can make fun of tourists and students.)

And I'm not just talking about NPC's Beats of Boston — I'm talking about the movies. For some reason, Hollywood loves to set films here. Most notable, of course, are the crime stories, from the classic era of The Thomas Crowne Affair (the Steve McQueen original) or The Boston Strangler, straight through to the Silver Age of vaguely nostalgic movies set in a rapidly gentrifying city longing for its grittier past: Mystic River, The Departed, Gone Baby Gone, Monument Ave., Spotlight, The Town, Black Mass, and more.

Added to this already impressive list are films in nearly every other genre, from legal dramas (The Verdict) and romances (Here Comes the Groom) to comedies from the city that can make and take a punchline as well as it can make and take a punch.

Better yet, many of these genres have been fused and blended into Boston's film history — the crime-comedy (The Brinks Job), the legal-comedy (Legally Blonde), the sports-comedy-romance (Fever Pitch) — a sort of natural inclination toward complexity that comes as no surprise to folks in a city where everything is complicated, and where even a simple request for directions to the nearest packie can wind up getting you stuck in a 90-minute exposition on local history, traffic, potholes, memories of epic snowstorms, the wisdom of Tip O'Neill, and the correct terminology for a drink made with milk, ice cream, and chocolate syrup.

There are lots of local explanations for this cinematic popularity. Some note that tons of great actors, directors, and writers come from the city or pass through it, making it a natural fit. The number of colleges — and the city's role in early U.S. history — might also help, as audiences are likely to be familiar with these landmarks and place names.

Added to this, Hollywood loves walkable neighborhoods as much as planners do. The narrow winding streets, the historic architecture, and the tight-knit communities provide great backdrops for tense cinematic drama and claustrophobic chase scenes. More obviously, the accents are funny, and the ethnic diversity plays well with Hollywood's desire to both represent and stereotype. The fact that Boston isn't New York or Los Angeles might also play a part — after all, everyone loves an underdog.

Regardless the reasons, all this attention means there are far too many Boston films to cover in one column alone, so I'm limiting my recommendations to just one for each of the following genres, of special interest to planners: stories of local politics and lives played out against the canvas of neighborhood change. Beyond these selections, if you're interested in more, check out the three-part podcast series from historic Brattle Theatre, which will introduce you to dozens of famous and lesser-known films set in the city.



For whatever reason, Boston seems to have as many crime stories as it has Dunkin' Donuts, making this by far the most competitive category. Interestingly, nearly all these tales are told from the perspective of the criminal element; other cities have cops, but Boston has crooks, usually down-and-out, washed-up, dead-end types.

No film brings this pathos to the screen better than Peter Yates's The Friends of Eddie Coyle. Made in 1973 — decades before The Departed, when Boston was truly as gritty and down-on-its-luck as the characters that populate those films — the great Robert Mitchum packed a generation's worth of despair, resignation, and existential angst into his 200-pound frame to portray small-time gunrunner Eddie "Fingers" Coyle in an adaptation of the novel of the same name (written by George Higgins, who also served as Assistant United States Attorney).

Along with some lesser-known locales (and the best Boston accents on film), the movie also features some great shots of the then-new City Hall Plaza, a windswept and desolate gap in the urban fabric created by the 1960s clearance and "renewal" of the old West End and Scollay Square neighborhoods. (And bonus: Eddie Coyle's partner in crime is played by none other than Alex Rocco, a real-world affiliate of the infamous Winter Hill gang who fled to Hollywood only to make a career playing racketeers, hit men, and wise-guys, including — ironically — Moe Greene, one of the few non-Italian characters in The Godfather.)



The scrappy confidence of the city is, perversely, most apparent in the pleasure Bostonians take in humor that mocks the accents, attitudes, and stereotypes of both Brahmans and townies alike. In this spirit of good-natured self-deprecatory humor, the nod for best Boston comedy goes to the city's longest-serving mayor, the incomparable and beloved Tom "Mumbles" Menino, for this Boston-based parody of The Godfather, produced by the nonprofit policy center, MassInc. It's hard to imagine most big city mayors being willing to poke fun at their own approach to downtown development, but by this point in his career, our "urban mechanic" was feeling pretty secure in his position.

(Runners up: this spot-on send-up of the city's loyalty to its favorite donut chain, and Seth Meyer's fake movie-preview for Boston Accent.)(Runners up: this spot-on send-up of the city's loyalty to its favorite donut chain, and Seth Meyer's fake movie-preview for Boston Accent.)



For a love story set in Boston, some will jump straight to Love Story, but that's a bit obvious (and also a bit insufferable); next, most people will recommend Good Will Hunting (there's a lot of town/gown potential in a working-class ethnic city that also hosts over 150,000 college students). It won Oscars, made star careers for Matt Damon and both Afflecks, and really did put Boston back on the map after a dry spell.

But since we're working on an "underdog theme" here, let's put in a plug for the feel-good sleeper Next Stop Wonderland. It's a perfect urban story of two people destined to meet in the big city, featuring a tour of tons of real locations, including the Public Garden, the historic South End, Copley Square, East Boston, the New England Aquarium, and the famously walkable Davis Square, Somerville.

And what planner doesn't love a film named after a subway stop?



Of course, in addition to being a setting for fiction and fun, Boston is also a very real city with rich history, politics, and planning, all of which can be explored through excellent documentary films. Notable selections include Fred Wiseman's City Hall (which I've previously reviewed), a chapter from the award-winning Eyes on the Prize series on the city's busing crisis, the story of the country's first underground subway, and a film on the Boston Marathon narrated by hometown hero Matt Damon.

But my own favorite documentary is Richard Broadman's Mission Hill and the Miracle of Boston. Made in 1978, the film serves as a magical time-capsule of a city struggling through a period of profound change, capturing the perspectives, hopes, fears, and sensibilities of long-time working-class residents facing urban renewal, demographic transition, and simultaneous forces of decline, development, and displacement. (And, best of all, since it's a documentary, all of the accents are spot-on, showcasing the full range of variation, tone, and nuance.)

Lastly, speaking of documentaries, please be sure to check out Land for a City on a Hill, the new short video tour on the history and development of Boston from Alex Krieger, professor and former chair of Harvard's Department of Urban Planning and Design. APA's local chapter host committee will be presenting the film, with a moderated discussion, on May 5, 2021, from 7-8PM.

Ezra Haber Glenn, AICP, is Planning's regular film reviewer. He teaches at MIT's Department of Urban Studies & Planning and writes about cities and film. Follow him on UrbanFilm and @UrbanFilmOrg.