Boston movies: The 11 wicked best

toutboston — Ben Affleck in 'The Town'; Matt Damon in 'Good Will Hunting'; Leonardo DiCaprio in 'The Departed'. Photo: Everett Collection (3)

What makes a great Boston movie? Well, often it includes at least Ben Affleck, Matt Damon, or Mark Wahlberg, but it takes more than just a famous New England product. The best Boston-area-based films feel real, lived-in, and authentic (there's nothing a Massachusetts native hates more than a bad Boston accent). The best Boston films embody the spirit of the city, for all of its upsides and downsides.

Here's EW's list of the 11 greatest Boston films, which happen to include eight Oscar nominees for Best Picture, a classic bank robbery movie, and the end of a curse.

01 of 11

The Departed (2006)

Matt Damon and Leonardo DiCaprio in 'The Departed'. Everett Collection

You couldn't ask for a better pedigree: Martin Scorsese directing; Brad Pitt producing; Matt Damon, Leonardo DiCaprio, and Mark Wahlberg starring; Jack Nicholson hamming it up as a Whitey Bulger-inspired kingpin; and 237 uses of the word "f---." The 2006 film delivered on its promise, winning Best Picture and, finally, scoring Scorsese his first Best Director trophy. About f---ing time.

02 of 11

Fever Pitch (2005)

Drew Barrymore and Jimmy Fallon in 'Fever Pitch'. Everett Collection

Red Sox fans have a love/hate relationship with Fever Pitch. Cons: It stars a Yankees fan, makes us look (rightfully) overly obsessive, and...it's not a great film. Pro: It can be looked at as a good luck charm, considering the ending had to be rewritten when the Sox won their first World Series in 86 years. Plus, it stars the ever-so-charming Drew Barrymore and the then-baby-faced Jimmy Fallon. And for that, Fever Pitch will always hold a special place in Boston movie history. Plus, at least it's better than Celtic Pride.

03 of 11

The Fighter (2010)

Mark Wahlberg and Amy Adams in 'The Fighter'. Everett Collection

Mark Wahlberg, one of Boston's favorite sons, leads the true story of boxer Mickey Ward. Yet, it's an actor from England and an actress from New York who steal David O. Russell's Best Picture nominee. For the roles of Ward's older brother struggling with drug addiction and controlling manager mom, respectively, Christian Bale and Melissa Leo won Best Supporting Actor and Actress at the Oscars. And still, it was the knockout casting of the family's seven sisters that really helped capture the area's essence.

04 of 11

Gone Baby Gone (2007)

Casey Affleck in 'Gone Baby Gone'. Everett Collection

Ben Affleck may be Batman and an Oscar-winning filmmaker, but in 2007, when he made his directorial debut, both of those future accomplishments would have been hard to picture. Ten years after scoring fame for Good Will Hunting, the actor was better known for who he was dating and big-budget failures like Daredevil. That changed with Gone Baby Gone, which starred his brother Casey Affleck as a P.I. looking into the disappearance of a young girl. Full of twists and dynamite performances from Affleck, Ed Harris, and an Oscar-nominated Amy Ryan, Gone didn't get the box office returns and acclaim that the director's later films would, despite being arguably as good.

05 of 11

Good Will Hunting (1997)

Matt Damon and Ben Affleck in 'Good Will Hunting'. Everett Collection

The Boston movie that birthed two Boston stars and so many subsequent Boston classics. Good Will Hunting served as the Hollywood coming-out party for childhood friends Matt Damon and Ben Affleck. In addition to starring in the film, the duo wrote the screenplay, for which they won an Oscar. As great as Damon is as the titular genius janitor and Affleck is as his loyal sidekick, it's Robin Williams — who also won an Oscar — delivering one of the best performances of his career that leaves us floored. We like them apples.

06 of 11

Manchester by the Sea (2016)

Michelle Williams and Casey Affleck in 'Manchester by the Sea'. Everett Collection

Casey Affleck returns to Massachusetts for his third go-around, but this time without his big brother — and the result is a tragic and heartbreaking performance as Lee Chandler, who must return to his hometown to care for his late brother's son. Upon his arrival, he must face his own devastating past, which leads to a scene between Affleck and Michelle Williams that's guaranteed to leave you drenched in tears. And while Affleck scored the Best Actor trophy and Williams a Best Supporting Actress nomination, then-19-year-old Lucas Hedges was writer-director Kenneth Lonergan's secret weapon.

07 of 11

Mystic River (2003)

Kevin Bacon and Sean Penn in 'Mystic River'. Everett Collection

Clint Eastwood's tale of childhood friends (Sean Penn, Kevin Bacon, and Tim Robbins) is an emotional gut punch from beginning to end. The Best Picture nominee finds the trio drawn back together following the death of Penn's daughter, Kate (Emmy Rossum) — and things only get more devastating from there. The stacked cast also includes Laurence Fishburne, Laura Linney, and Marcia Gay Harden, but Penn and Robbins — both Oscar winners for their roles — especially shine as the grieving father and the emotionally (and physically) scarred suspect.

08 of 11

Spotlight (2015)

Rachel McAdams, Mark Ruffalo, Brian d'Arcy James, Michael Keaton, and John Slattery in 'Spotlight'. Everett Collection

Tom McCarthy's Best Picture winner proved you don't need a famous native (sorry, John Slattery) to make a great Boston film. Michael Keaton, Rachel McAdams, and Mark Ruffalo excel in the true story of The Boston Globe's special investigative team that exposed widespread child abuse in the Catholic church.

09 of 11

The Town (2010)

Ben Affleck and Jeremy Renner in 'The Town'. Everett Collection

Ben Affleck returned to Boston for his sophomore directorial effort, although for The Town, he stepped in front of the camera as well, starring as Doug McRay, the head of a crew of bank robbers. Affleck, Rebecca Hall, and Jon Hamm are all great, but Jeremy Renner has never been better as Jem, McRay's menacing partner-in-crime. And he might have the most badass Boston line in movie history when Affleck offers no details in a request for his friend's help in beating up some neighborhood guys. Stone-faced, Jem responds, "Whose car are we gonna take?"

10 of 11

The Verdict (1982)

Paul Newman in 'The Verdict'. Everett Collection

Contrary to what the previous nine films may have led you to believe, there were good Boston movies made before Ben Affleck and Matt Damon showed up on the scene. And the class of this era was Sidney Lumet's celebrated courtroom drama, which landed Paul Newman one of his eight Best Actor nominations for the role of a disgraced lawyer revitalized by a new case.

11 of 11

The Holdovers (2023)

Dominic Sessa, Da'Vine Joy Randolph, and Paul Giamatti in 'The Holdovers'.
Seacia Pavao/FOCUS FEATURES

This Oscar-nominated period comedy-drama is primarily set at a New England boarding school, where a teacher (Paul Giamatti) looks after a student (Dominic Sessa) who has nowhere to go over the holiday break. They agree to take an extended field trip to Boston, touring the city as it looked in the '70s, which was recreated by the film's production designers. —Kevin Jacobsen

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