The tenth anniversary of the iconic heist movie The Town is Sept. 17, which means it’s a great time to revisit not just the film about a group of bank robbers from Charlestown, but also the surprisingly expansive Boston film genre and its incredibly popular sub-genre Boston Crime. To help you figure out what to watch, we’ve put together a list of the best Boston movies to stream.
Now, the films on this list might not be the best movies ever made (though some are definitely excellent), but they feel authentic and lived in, feature the famous Boston accent (for better or worse), and often star a number of famous Boston-area natives — OK, it’s mostly Ben Affleck, Matt Damon, and Mark Wahlberg (sorry, Chris Evans — you’ll get there one day), but that’s like the holy trinity, right? So if you’re looking for some great Boston movies to watch, these are the best ones.
Looking for more recommendations of what to watch next? We have a ton of them! And if you’re looking for hand-picked recommendations based on shows you love, we have those too.
Watch it on: Netflix
Ben Affleck and Jeremy Renner, The TownPhoto: Legendary Pictures
Say what you will about Ben Affleck as a person — or as a shill for Dunkin’ — but when it comes to Ben Affleck as a man who makes movies set in Boston, Massachusetts, he’s the undefeated champ. The Town, the 2010 film he co-wrote, directed, and starred in, is an undeniably great heist film with a high rewatchability factor. Affleck stars as Doug MacRay, a bank robber from Charlestown who hopes to pull off one final score with a group of lifelong friends by robbing Fenway Park and then skipping town for greener pastures. However, his heart gets tangled up with the one person who could identify Doug and his friends from an earlier heist, and soon his big plan threatens to fall apart. Between Affleck’s impressive direction, an excellent and memorable supporting turn from Jeremy Renner, who received his second Academy Award nomination for the performance, and the fact Affleck cast real Boston residents to make it authentic, The Town is an all-time great Boston movie.
Good Will Hunting
Watch it on: Showtime, Hulu (with Showtime add-on), Amazon Prime (to buy)
The 1997 film that introduced most of the world to best friends Matt Damon and Ben Affleck, Good Will Hunting received a number of award nominations and even earned the pair the Academy Award for Original Screenplay. Damon stars in the film as Will, a self-taught genius from an abusive foster home who as an adult works as a janitor at MIT. Through a series of events, he comes to study with a renowned mathematics professor and eventually finds a path out of South Boston and to a better life, a development that pleases his friend Chuckie (Affleck) to no end. There’s a good chance you’ve already seen this movie, but it never gets old, and it features a number of the same Boston-centric themes as other films on this list.
Watch it on: HBO Max
Leonardo DiCaprio, The DepartedPhoto: -, Andrew Cooper
The best Boston-set movie ever made, The Departed is one of those films you have to watch every time it pops up on TV (remember just watching stuff because it was on?). A remake of the Hong Kong film Internal Affairs directed by Martin Scorsese — who finally took home an Oscar for directing for the film — the gangster drama tells an increasingly tense story of two cops — one who’s infiltrated the crew of notorious crime boss Frank Costello (played by Jack Nicholson) in an attempt to bring him down, and one who’s working for him as a mole in the BPD and attempting to protect him from within. When they each find out the other exists, they go to great lengths to discover the other’s identity while protecting their own. The movie featured a truly ridiculous cast — in addition to Nicholson, the film starred Leonardo DiCaprio and Matt Damon as the two cops, and featured supporting work from Martin Sheen, Mark Wahlberg, Alec Baldwin, Vera Farmiga, and one infamous rat — and, as a bonus, gifted us with some of Marky Mark’s best work to date.
Watch it on: Netflix
SpotlightPhoto: KERRY HAYES
Spotlight isn’t like the other Boston movies on this list; the 2015 winner of the Academy Award for Best Picture isn’t a gritty mystery or a film steeped in gangster themes. It is based on the true story of The Boston Globe’s “Spotlight” team — a group of investigative journalists — who uncovered widespread, systemic child sex abuse in the Boston area by an astonishing number of Catholic priests. The series of stories published by the Globe on the topic earned the newspaper a Pulitzer, and although the film took some creative liberties in telling this story, it’s an engrossing, moving, and well-acted film that honors the work of its subjects.
Watch it on: Amazon Prime (to buy)
Mystic RiverPhoto: UPDATE
Based on the Dennis Lehane novel of the same name, Mystic River tells the story of three childhood friends — played by Tim Robbins, Sean Penn, and Kevin Bacon — who are drawn back together as adults after the murder of one of their daughters. As secrets are revealed, tensions rise, and distrust forms, layers of tragedy are revealed, and the film, which was directed by Clint Eastwood, becomes one emotional gut punch after another. The movie stands out for its impressive cast — which also includes Laurence Fishburne, Marcia Gay Harden, and Laura Linney — and their even more impressive performances.
The Boondock Saints and The Boondock Saints II: All Saints Day
Watch it on: Amazon Prime (to buy)
The Boondock Saints II: All Saints DayPhoto: Apparition/Everett Collection
In my experience, you either love The Boondock Saints, a violent vigilante crime drama that has gained a cult following over the years, or you hate it. There is no in between. The 1999 Boston movie stars a pre-Walking Dead Norman Reedus and Sean Patrick Flanery as Irish American twin brothers who, after killing members of the Russian mafia in defense, embark on a life of vigilantism in an attempt to rid the city of Boston of crime, as if that’s possible. They’re pursued by Willem Dafoe’s FBI agent, which culminates in a memorable sequence involving a firefight. Despite its critical reputation as a failure, the film has many fans and even spawned a sequel, The Boondock Saints II: All Saints Day, which picks up eight years after the original.
Gone Baby Gone
Watch it on: Starz, Hulu (with Starz add-on), Amazon (with Starz add-on)
Gone Baby GonePhoto: Photo Credit: Claire Folger
Oh look, another movie connected to the Affleck family. Apparently it’s impossible to make a good Boston-set movie without at least one Affleck. Jokes aside, Gone Baby Gone is the film that turned Ben’s career around; it was his feature-length directorial debut, and he also co-wrote the script, which was based on another one of Dennis Lehane’s novels. A neo-noir set in the Boston neighborhood of Dorchester, the film explores Boston’s seedy underbelly and stars Casey Affleck and Michelle Monaghan as two PIs searching for a young girl who was abducted from her home. The mystery follows a number of twists and turns, and is one that stays with you long after you’ve watched.
Watch it on: Showtime, Hulu (with Showtime add-on), Amazon Prime (with Showtime add-on)
Fever PitchPhoto: Fox Pictures/Hulu
Admit it, you were not expecting to see Fever Pitch, a rom-com starring Jimmy Fallon and Drew Barrymore, on this list that features mostly what amounts to Boston Crime Movies. But the film deserves to be on this list, not because it’s an incredible feat of filmmaking — it’s really, really not — but because it captures a different side of the city and a specific moment in time: when the Red Sox reversed the curse and won the World Series in 2004. Sure, Boston went on to win three more times through 2018, annoying pretty much every baseball fan outside the greater Boston area, but this was a big moment for Boston sports, and for sports history, so even if you now root against the egotistical Red Sox, this film is an important one to watch.