FEVER PITCH (2005)

Fever Pitch is one of the best Beantown comedies because so many Boston sports fans can relate to Jimmy Fallon’s character. We’re a die-hard sports city, and we’re dedicated to our teams, whether we win or lose, just like Fallon’s Ben Wrightman. And while, yes, we’ve been blessed over the last 20 years with stellar sports teams, it wasn’t really until around the time Fever Pitch was being made that we became blessed with our baseball team. In a sense, this movie has become a good luck charm for us and the Red Sox. We hadn’t won a World Series in more than 80 years, so when the Sox finally won the World Series in 2004, our city rallied around this movie. They even had to rewrite the ending to capture that special feeling and excitement of finally winning. It makes the movie truly something special to rewatch, even when some of the jokes don’t hit it out of the park. 

SPOTLIGHT (2015)

While Spotlight is more of a journalism movie than a full-blown Boston movie with regard to its aesthetic, it is based on the true story of several Boston Globe reporters working together to blow the lid off the biggest criminal corruption that had been occurring within the Catholic church. Frankly, it’s no wonder this film won Best Original Screenplay and Best Picture at the Oscars. It’s extremely unsettling, but also a powerful film that reveals the truth of this tragedy. It does a fascinating job depicting this real-life story, and through its phenomenal writing and perfectly balanced ensemble, including Mark Ruffalo, Michael Keaton, and Rachel McAdams, this gem really elevates the reputation of the reporters to hero status. Although these horrible crimes happened across the U.S., the fact that a Boston newspaper was able to break the case shows that Bostonians aren’t only tough badasses, but also are wicked smart.

GONE BABY GONE (2007)

This gritty mystery proved that Ben Affleck has what it takes to step behind the camera and become one of the best filmmakers working today. In his directorial debut, based on Dennis Lehane’s book, we get the other Affleck (Casey Affleck) as a private investigator looking into the disappearance of a little girl with the help of his girlfriend, played by Michelle Monaghan. Gone Baby Gone is one of those films that won't be gone from your mind after you see it. It’s a gripping crime thriller that is full of twists and turns you won’t see coming. Plus, it’s filled to the brim with dynamite performances from Ed Harris, Morgan Freeman, and Amy Ryan (who was nominated for Best Supporting Actress), all of whom help bring Boston’s working class to life with their lived-in and raw portrayals. I must say Ben Affleck truly found his calling with this film, and it’s making stellar movies set in Boston.

MYSTIC RIVER (2003)

One of the most gripping Boston-set films is Clint Eastwood’s Mystic River. This Best Picture nominee has such a captivating story of three childhood friends (played by Sean Penn, Kevin Bacon, and Tim Robbins) whose lives are forever altered after a tragic occurrence. But Mystic River isn’t just another gritty film revolving around a criminal act in Boston; it’s so much deeper than that. The film explores themes of revenge, loyalty, and trauma that are delivered so well through its writing and performances, especially by Penn, who won Best Actor for this role. This is personally my favorite Eastwood movie, and while some of the Boston accents are hit and miss (I’m talking to you, Tim Robbins), there’s no denying that this film captures a rawness that a lot of Bostonians can relate to.

THE FIGHTER (2010)

Not only is The Fighter one of the best movies set in Boston, but it’s honestly one of the best boxing films to date. This sports biopic based on the professional boxer Micky “Irish” Ward, played by the Boston bad boy himself, Mark Wahlberg, is such a soulful story that will punch you right in the gut. This character-driven drama is heartbreaking and inspiring all at once, and it’s more than just a boxing movie - it's a movie about the struggles within this family unit. While the actual fights may take place in the ring, the real battle is going on outside the ropes amongst the family members, which is what really draws your attention to this stellar story. With a knockout cast including Wahlberg, Christian Bale, Amy Adams, and Melissa Leo, there’s no denying you're in for a treat. Both Bale and Leo won Best Supporting Actor and Supporting Actress, respectively, for their work here, giving maybe the best performances of their careers. They deserve all the praise for nailing the Boston accent too, which makes us Bostonians extremely proud.

THE DEPARTED (2006)

Contrary to popular belief, The Departed is not based on the famous Boston criminal Whitey Bulger, even though it sure feels like it. It’s actually a remake of the Hong Kong film Internal Affairs. This riveting gangster drama stars some of the biggest names in Hollywood, from Jack Nicholson and Leonardo DiCaprio to some of our favorite Bostonian actors, Matt Damon and Mark Wahlberg. In addition to its phenomenal ensemble (I'm still baffled at how Mark Wahlberg was the only actor in this masterpiece to get nominated for an Oscar), it’s directed by the legendary Martin Scorsese, who directed the fucking hell out of this film, leading it to not only win Best Picture at the Academy Awards, but also netting Scorsese his first and (to date) only Best Director Oscar. This movie drips with authentic Boston vibes, from its nitty-gritty underground gangster crime story to casually throwing the F-bomb around 237 times. And, oh man, while that ending shot may be considered divisive (which baffles me), it’s personally one of my favorite symbolic endings in any film. At the end of the day, not only is The Departed a top-tier Scorsese film, it’s a top-tier Boston flick.

GOOD WILL HUNTING (1997)

The movie that birthed two of the biggest Boston names, Matt Damon and Ben Affleck, catapulting them to Hollywood success, is Good Will Hunting. Without this film, we may have never gotten these two brilliant and talented men, a duo that ended up winning Best Original Screenplay for this gem. What they were able to capture in this coming-of-age story is not only raw but elegantly masterful. We also got one of my favorite performances from my favorite actor, Robin Williams, who deservedly won an Oscar for his portrayal as the therapist to Damon’s character. This story about a few guys from Southie learning the importance of thinking for themselves and overcoming the trauma in their lives is something that many can connect with, even if you're not from our neck of the woods. Overall, this film opened the floodgates to the Boston scene, and its existence has influenced many Boston-set films. I don’t know about you, but I sure as hell liked them apples and this movie!

THE TOWN (2010)

The most wicked awesome Boston movie on my list goes too… The Town! In my opinion, it’s the most authentic Boston-based film, from the raw performances and stellar accents (Jeremy Renner gets two thumbs up in my book for the best Boston accent from a non-Bostonian) to attempting to pull off the most epic heist in robbing Fenway Park. Having shot these brutal action sequences in and around the neighborhoods of Boston makes this flick all the more rich and magical. Ben Affleck does a phenomenal job in front of and behind the camera in what I consider his best film to date, and what he’s able to capture in this tense and exhilarating drama makes it one of the best modern heist films. Loosely adapted from Chuck Hogan's 2004 novel Prince of Thieves, The Town follows a group of guys from Charlestown who gravitate towards a life of crime, robbing banks and armored cars, and the difficulties of being unable to escape their circumstances. The filmmakers even managed to work with real-life Boston criminals to provide in-depth details to make the story and robberies feel that much more enhanced and real. If that ain’t Boston enough for you, I don’t know what is.