12 Binge-Worthy Boston Movies to Cozy Up With This Winter

Pahk yah cah, grab a beer, and escape with these Boston-based hits.

by Morgan Rousseau
January 20, 2022

Cover photo courtesy Getty Images

Boston is a city known for its American history, its relentlessly victorious sports teams, and — of course — its baked beans. But the city’s no slouch when it comes to setting the scene for some of cinema’s most memorable movies.

Whether you’re a local or just a fan of its flicks, here’s the ultimate list of iconic Boston films — and some fun facts to boot. We like them apples. 

1. Good Will Hunting (1997)

Childhood friends Matt Damon and Ben Affleck wrote Good Will Hunting together — and earned themselves an Oscar for Best Original Screenplay. Though both stars are exalted as the ultimate Boston boys, they actually hail from Cambridge, Massachusetts. Robin Williams also gives a remarkable performance in this one (and nails the accent), earning himself a Best Supporting Actor Oscar.

In it, Damon stars as Will Hunting, a mathematically gifted janitor at the Massachusetts Institute of Technology (MIT) who makes an unlikely connection with a psychologist (Williams) to find his life’s direction.

Both Damon and Affleck were 27 and 25, respectively, when they won their first Oscars for this critically acclaimed hit.

2. The Departed (2006)

Another Matt Damon one here. Based on the 2002 Hong Kong action thriller, Infernal Affairs, The Depahted (we had to) featured an all-star cast that included Damon, Leonardo DiCaprio, Mark Wahlberg, and Jack Nicholson (based loosely on Boston’s most notorious gangster, James “Whitey” Bulger. More on him below). The Departed won an Oscar for Best Picture and snagged its director Martin Scorsese a Best Director award.

3. Mystic River (2003)

Starring Sean Penn, Kevin Bacon, and Tim Robbins, Mystic River is a dark yet poignant story of Boston childhood friends and their connection to a harrowing past and tragic future. Clint Eastwood directed and scored the film, which was based on the 2001 novel of the same name.

Penn and Robbins won Oscars for Best Actor and Best Supporting Actor, respectively.

4. The Perfect Storm (2000)

Though The Perfect storm isn’t set in Boston (it’s set in Glouster, about 35 miles north), it flaunts the thickest New England accents possible. Also, it stars Mark Wahlberg—a bonafide Boston boy. 

The film tells the tragic true story of a commercial fishing vessel that was lost at sea, along with its entire crew, in the so-called Perfect Storm of 1991. George Clooney, Diane Lane, and John C. Reilly also star in the hit movie, which grossed $328 million worldwide.

5. Spotlight (2015)

Another Oscar-winning film, Spotlight tells the true story of The Boston Globe’s stellar investigative reporting of child abuse in the Roman Catholic Archdiocese of Boston. It stars Michael Keaton, Mark Ruffalo, and Rachel McAdams, and won Oscars for Best Picture and Best Original Screenplay.

Much of Spotlight’s filming took place in the former Boston Globe offices in Dorchester, as well as the Boston Public Library.

6. The Town (2010)

These Afflecks — they really love their Massachusetts roots. Directed by and starring Ben Affleck, The Town tells the story of a crew of childhood friends-turned bank robbers who hail from Charlestown, which is Boston’s oldest neighborhood. Jeremy Renner steals the show in this one — along with a few other things. Fun fact: Charlestown locals performed as extras.

7. Gone Baby Gone (2007)

Ben Affleck’s directorial debut stars brother Casey Affleck as a private investigator probing the disappearance of a local girl. Gone Baby Gone was filmed in South Boston, with plenty of locals acting as extras.

8. Black Mass (2015)

Another gangster flick, Black Mass tells the true life story of Boston’s most notorious mobster,  James “Whitey” Bulger. The film stars Johnny Depp as Bulger, the famed leader of Somerville’s Winter Hill Gang, which had a stronghold on most organized crime in the city through the 70s and 80s until he went into hiding in 1994. Depp portrays Bulger’s famous Santa Monica arrest in 2011. 

9. Manchester by the Sea (2016)

Another one that isn’t based directly in Boston, but rather on the North Shore, Manchester by the Sea stars Casey Affleck and Michelle Williams. The tear-jerking film won Affleck an Oscar for Best Actor. The Office and A Quiet Place star John Krasinski — whose hometown is the Boston suburb of Newton — was one of the executive producers on the film.

10. The Boondock Saints (1999)

Long before his Walking Dead fame, actor Norman Reedus starred in The Boondock Saints. The film focuses on two Irish Catholic vigilante twin brothers who take on Boston’s criminal underworld in the name of God. Another fun fact: Mark Wahlberg passed on a role as one of the brothers so he could star as porn heartthrob Dirk Diggler in the 1997 flick Boogie Nights

11. Shutter Island (2010)

With his Boston box-office hits, you’d think Martin Scorsese was a local (let’s be real, he’s all NYC). Set in 1954, Shutter Island is a psychological thriller based on a best-selling novel of the same name. It stars one of Scorsese’s favorites, Leonardo DiCaprio, as a U.S. Marshal investigating a creepy mental hospital. The film was shot at Medfield State Hospital just 20 miles southwest of the city. 

12. Ted (2012)

After all that darkness and drama, we’ve gotta end on a light note. Boston-based movies tend to have a heavy note, but Mark Wahlberg and Seth MacFarland’s partnership in Ted brought the laughs — and the box office clout. Best of all, the comedy highlights some of the city’s most iconic locations, including the New England Aquarium, the Esplanade, and the Green Monster (Fenway Park). 

Morgan Rousseau is a journalist, writer, and editor who has worked with Boston Globe Media Partners, Hearst, News Corp, Gannett, and Metro US.