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The 32 best Boston movies (and how to watch them)
The best Boston movies range from crime dramas like "The Departed" to side-splitting comedies like "Ted" and "The Heat." Here's how to watch them on your favorite streaming service or on demand.
How do you define a “Boston movie”?
Ask the average person, and the answer likely involves a film in which streetwise characters played by Matt Damon, an Affleck, or a Wahlberg drop their proverbial gloves as frequently as they drop their Rs.
But the truth is, the Boston movie canon is much deeper and more varied than the avalanche (or maybe nor’easter?) of Boston crime movies that took over cineplexes in the early 2000s.
The very first movie shot in the state — an adaptation of Washington Irving’s “Rip Van Winkle” filmed on the Cape in 1896 — is older than Hollywood itself. The first major Hollywood production to set up shop in Boston — the 1950 noir “Mystery Street” — hinted at the decades of Boston crime movies to come.
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There are movies shot all over Massachusetts that retain the Boston movie spirit. Cambridge may be its own municipality, but films shot at Harvard just across the river from Boston like “The Social Network” and “Love Story” belong in the conversation. So do North Shore movies featuring working class heroes like “The Perfect Storm” and “CODA.”
And you know that there’s a fair share of Boston-area vacationers populating the Cape and the islands in movies like “American Fiction” and 1975’s “Jaws,” which turned Martha’s Vineyard into one big film set for six months in 1974.
In that inclusive spirit, we decided to title our Boston movie bracket “Massachusetts Movie Madness,” which features 32 films shot all over the Bay State. While we’ve asked Boston.com readers to vote on the very best of the bunch, we think all 32 of are worth watching.
The 32 best Boston movies (and how to watch or stream them)
“American Fiction” (2023)
Runtime: 117 min.
Starring: Jeffrey Wright, Sterling K. Brown, Issa Rae, Erika Alexander
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This sharp Oscar-winning satire stars Jeffrey Wright as Monk, a Boston writer who writes a laughably stereotypical novel under a pseudonym as a commentary on the commodification of Black identity – and is driven mad when it becomes a hit.
How to watch: “American Fiction” is streaming on Prime Video and MGM+.
“Between The Lines” (1977)
Runtime: 101 min.
Starring: John Heard, Jeff Goldblum, Lindsay Crouse
Capturing the renegade spirit of alt-weeklies like the dearly departed Boston Phoenix, “Between the Lines” features early-career turns from John Heard as a jaded reporter and Jeff Goldblum as a cocky music critic.
How to watch: “Between the Lines” is streaming on Tubi.
“A Civil Action” (1998)
Runtime: 125 min.
Starring: John Travolta, William H. Macy, John Lithgow, Robert Duvall, Kathleen Quinlan
The wave of 1990s court dramas reached Boston with this true story of a lawyer (John Travolta) fighting for the residents of Woburn whose contaminated drinking water has been killing them.
How to watch: “A Civil Action” is available to rent on demand.
“CODA” (2021)
Runtime: 111 min.
Starring: Emilia Jones, Eugenio Derbez, Troy Kotsur
This film about a Gloucester teen on the verge of joining her deaf family in the fishing business was the feel-good hit of the early pandemic, winning Best Picture in the process.
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How to watch: “CODA” is streaming on Apple TV+.
“The Departed” (2006)
Runtime: 151 min.
Starring: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen
This Martin Scorsese movie has it all: Damon and DiCaprio playing cat and mouse, Mark Wahlberg in the role he was born to play, and Jack Nicholson as the Whitey Bulger stand-in, watching it all unfold.
How to watch: “The Departed” is streaming on Philo.
“Fever Pitch” (2005)
Runtime: 104 min.
Starring: Drew Barrymore, Jimmy Fallon
A better-than-average romantic comedy gained added meaning when the Red Sox reversed the curse and won the team’s first World Series in 86 years, forcing the Farrelly Brothers to change the movie’s ending on the fly.
How to watch: “Fever Pitch” is available to rent on demand.
“The Fighter” (2010)
Runtime: 116 min.
Starring: Mark Wahlberg, Christian Bale, Amy Adams, Melissa Leo
Hometown hero Mark Wahlberg (playing boxer Micky Ward) anchors this sports drama, but it’s Christian Bale as his brother, Dicky, and Melissa Leo, as his mother, Alice, who deservingly took home the Oscars.
How to watch: “The Fighter” is available to rent on demand.
“The Friends of Eddie Coyle” (1973)
Runtime: 103 min.
Starring: Robert Mitchum, Peter Boyle, Richard Jordan, Steven Keats
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There’s nothing glamorous about Eddie Coyle (Robert Mitchum), a low-level hoodlum scrambling to survive in Boston’s seedy underbelly – which is exactly what makes this film the ultimate Boston crime movie.
How to watch: “The Friends of Eddie Coyle” is streaming on Pluto TV.
“Gone Baby Gone” (2007)
Runtime: 114 min.
Starring: Casey Affleck, Michelle Monaghan, Morgan Freeman, Ed Harris, Amy Ryan
Ben Affleck’s directorial debut gives younger brother Casey his time in the spotlight, playing a private investigator searching for a missing Dorchester girl.
How to watch: “Gone Baby Gone” is streaming on Pluto TV.
“Good Will Hunting” (1997)
Runtime: 126 min.
Starring: Robin Williams, Matt Damon, Ben Affleck, Stellan Skarsgård, Minnie Driver
Matt Damon had to fight this movie’s original studio to film in Boston instead of Canada, saying that he and co-writer Ben Affleck saw the city as another character in the movie. Thank goodness they did.
How to watch: “Good Will Hunting” is streaming on Paramount+ and Pluto TV.
“Glory” (1989)
Runtime: 122 min.
Starring: Matthew Broderick, Denzel Washington, Cary Elwes, Morgan Freeman
This Civil War drama about the 54th Massachusetts Infantry Regiment focuses on the exploits of Colonel Robert Gould Shaw (Matthew Broderick), but it’s Denzel Washington – in an Oscar-winning performance as Private Trip – who steals the show.
How to watch: “Glory” is streaming on MGM+.
“The Heat” (2013)
Runtime: 117 min.
Starring: Sandra Bullock, Melissa McCarthy
Sandra Bullock and Melissa McCarthy are a riot in this buddy comedy, playing an FBI agent and BPD detective with clashing personalities who team up to take down a Boston mobster.
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How to watch: “The Heat” is streaming on Hulu.
“Hocus Pocus” (1993)
Runtime: 96 min.
Starring: Bette Midler, Sarah Jessica Parker, Kathy Najimy
A lot of this campy family comedy was shot in California, but the exteriors – and the witchy ambiance – are all Salem.
How to watch: “Hocus Pocus” is streaming on Disney+.
“The Holdovers” (2023)
Runtime: 133 min.
Starring: Paul Giamatti, Da’Vine Joy Randolph, Dominic Sessa
Alexander Payne’s holiday drama – about the last three people (Paul Giamatti, Dominic Sessa, Da’Vine Joy Randolph) stuck at a New England prep school over Christmas break – leaves your heart full when the credits roll.
How to watch: “The Holdovers” is streaming on Peacock.
“Jaws” (1975)
Runtime: 124 min.
Starring: Roy Scheider, Robert Shaw, Richard Dreyfuss
It took six months of shooting, reshooting, and cutting around the malfunctioning mechanical shark, but Steven Spielberg ultimately produced one of the most suspenseful movies of all time and gave birth to the modern blockbuster.
How to watch: “Jaws” is streaming on Peacock.
“Knives Out” (2019)
Runtime: 130 min.
Starring: Daniel Craig, Chris Evans, Ana de Armas, Jamie Lee Curtis, Michael Shannon, Don Johnson, Toni Collette
Rian Johnson’s mystery-comedy brilliantly portrays the type of old-money suburban Boston family whose scions justifiably feel like they could get away with murder – as long as detective Benoit Blanc (Daniel Craig) doesn’t show up.
How to watch: “Knives Out” is streaming on Prime Video.
“Legally Blonde” (2001)
Runtime: 96 min.
Starring: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, Jennifer Coolidge
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Reese Witherspoon never set foot on the real Harvard campus (that’s USC you see on screen), but this comedy’s legacy is undeniable, with an upcoming TV series and film sequel in the works.
How to watch: “Legally Blonde” is available to rent on demand.
“Little Women” (2019)
Runtime: 135 min.
Starring: Saoirse Ronan, Emma Watson, Florence Pugh, Eliza Scanlen, Laura Dern, Timothée Chalamet, Meryl Streep
Greta Gerwig’s adaptation of Louisa May Alcott’s novel is a timeless story of sisterly bonds, of unrequited love, and of unbowed ambition.
How to watch: “Little Women” is available to rent on demand.
“Love Story” (1970)
Runtime: 101 min.
Starring: Ali MacGraw, Ryan O’Neal
“Love means never having to say you’re sorry” is just one of the lasting cultural contributions from this Harvard-set melodrama, which set the template for the next half-century of romantic stories told on screen.
How to watch: “Love Story” is streaming on Kanopy.
“Manchester by the Sea” (2016)
Runtime: 137 min.
Starring: Casey Affleck, Michelle Williams, Kyle Chandler, Lucas Hedges
Casey Affleck is heartbreaking in his Oscar-winning role as a North Shore janitor whose life has been shaped by unspeakable tragedy, but brightens ever-so-slightly when his nephew (Lucas Hedges) moves in.
How to watch: “Manchester by the Sea” is streaming on Prime Video.
“Monument Ave.” (1998)
Runtime: 93 min.
Starring: Denis Leary, Colm Meaney, Famke Janssen, Martin Sheen
Denis Leary lived and worked as a painter in Charlestown before making it as a stand-up comic, so it’s no wonder his crime thriller captures the neighborhood vibe so perfectly.
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How to watch: “Monument Ave.” is available to rent on demand.
“Mystic River” (2003)
Runtime: 138 min.
Starring: Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, Laura Linney
Clint Eastwood’s film is the darkest of the Boston crime movies, chronicling generations of suffering centered around a trio of childhood friends (Sean Penn, Tim Robbins, Kevin Bacon) who are drawn back together by an unsolved murder.
How to watch: “Mystic River” is available to rent on demand.
“Next Stop Wonderland” (1998)
Runtime: 104 min.
Starring: Hope Davis, Alan Gelfant, Philip Seymour Hoffman
Brad Anderson’s indie romcom benefitted from the success of “Good Will Hunting,” getting distribution from Miramax for this story of a single woman (Hope Davis) who goes on a dozen terrible dates, all while the perfect partner (Alan Gelfant) is just out of frame.
How to watch: “Next Stop Wonderland” is available to rent on demand.
“The Perfect Storm” (2000)
Runtime: 130 min.
Starring: George Clooney, Mark Wahlberg, Diane Lane, William Fichtner
The true story of the sinking of the Andrea Gail in 1991 boasts strong performances from Mark Wahlberg, George Clooney, and John C. Reilly as Gloucester fisherman.
How to watch: “The Perfect Storm” is streaming on Philo.
“School Ties” (1992)
Runtime: 107 min.
Starring: Brendan Fraser, Matt Damon, Chris O’Donnell, Cole Hauser, Ben Affleck
Five years before “Good Will Hunting,” this prep school drama was an early showcase for Matt Damon, Ben Affleck, and a half-dozen other future Hollywood stars.
How to watch: “School Ties” is streaming on Paramount+.
“Shutter Island” (2010)
Runtime: 137 min.
Starring: Leonardo DiCaprio, Mark Ruffalo, Ben Kingsley, Michelle Williams
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What do you get when you cross Martin Scorsese, Leonardo DiCaprio, and a Dennis Lehane novel? An eerie neo-noir with a hell of a twist.
How to watch: “Shutter Island” is streaming on Pluto TV.
“The Social Network” (2010)
Runtime: 120 min.
Starring: Jesse Eisenberg, Andrew Garfield, Justin Timberlake, Armie Hammer
Come for the career-best performances from Jesse Eisenberg and Andrew Garfield, stay for the word-perfect Aaron Sorkin script, which turns the origin story of Facebook into high drama.
How to watch: “The Social Network” is available to rent on demand.
“Spotlight” (2015)
Runtime: 129 min.
Starring: Mark Ruffalo, Michael Keaton, Rachel McAdams, Liev Schreiber, John Slattery, Stanley Tucci
The Best Picture winner is similar to the Boston Globe journalists it portrays – quiet, efficient, but packs a powerful punch when the big story finally comes together.
How to watch: “Spotlight” is streaming on Prime Video.
“Ted” (2012)
Runtime: 106 min.
Starring: Mark Wahlberg, Mila Kunis, Seth MacFarlane
Seth MacFarlane may be from Connecticut, but he has an ear for Boston, as made evident by this buddy comedy with Mark Wahlberg and a foul-mouthed teddy bear.
How to watch: “Ted” is available to rent on demand.
“The Thomas Crown Affair” (1968)
Runtime: 102 min.
Starring: Steve McQueen, Faye Dunaway
“The Thomas Crown Affair” gave us an on-screen couple for the ages, with bored playboy turned thief Thomas Crown (Steve McQueen) playing cat and mouse with the insurance investigator determined to bring him down (Faye Dunaway).
How to watch: “The Thomas Crown Affair” is streaming on Tubi, Pluto TV, The Roku Channel, and Prime Video.
“The Town” (2010)
Runtime: 124 min.
Starring: Ben Affleck, Rebecca Hall, Jon Hamm, Jeremy Renner, Blake Lively
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The scene in which Ben Affleck’s gang of Charlestown bank robbers enter Fenway Park may be the best action setpiece ever filmed in this city.
How to watch: “The Town” is streaming on Netflix.
“The Verdict” (1982)
Runtime: 129 min.
Starring: Paul Newman, Charlotte Rampling, Jack Warden
Paul Newman deserved an Oscar for his role as world-weary attorney Frank Galvin, whose life gains renewed meaning when he pursues a medical malpractice suit on behalf of a comatose woman.
How to watch: “The Verdict” is available to rent on demand.
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