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The Toast Of Beantown: Boston's Best Movies

Evan Crean Evan Crean
October 30th, 2009 10:32am EDT
The Boondock SaintsIn 1999, Troy Duffy showed audiences that New York City isn't the only major metropolitan place where mob violence and nefarious dealings happen on film. Using Boston as a backdrop for his cult hit "Boondock Saints," Duffy gave the city a gritty image that reignited interest in the area.

"Boondock Saints" follows the MacManus brothers, a pair of vigilantes who decide to carry out their own brand of violent justice on the criminals of Boston. As a proud Boston resident, I'm thrilled to announce the premiere today of "Boondock Saints II: All Saints Day," which brings the MacManus brothers back to seek revenge on the mob boss who has framed them for murder.

To honor the release of this film, I've assembled a list of the best movies that take place in Beantown.

5. MYSTIC RIVER

Clint Eastwood's thoughtful crime thriller involves the intertwining lives of three childhood friends: Jimmy Markum (Sean Penn), Sean Devine (Kevin Bacon), and Dave Boyle (Tim Robbins).

During the summer of 1975, while the three are playing on a street in Boston, Dave is abducted by two men who sexually abuse him over a period of several days. Dave escapes from them but he is haunted into adulthood by his traumatic experience.

Back in the present day, Jimmy's daughter Katie is found murdered. Dave becomes the prime suspect, and Sean is the officer assigned to investigate the crime. An ex-con, Jimmy threatens violence on the person responsible for his daughter's death, while Sean battles his own personal demons and tries to keep Jimmy wrath's at bay.

Unable to contain his rage, Jimmy exacts revenge on the person he feels is responsible for his daughter's death. Jimmy, Dave, and Sean's lives are changed irrevocably as a result.


Penn, Bacon, and Robbins all deliver powerful performances in their respective roles. From a directing perspective Clint Eastwood does an excellent job of conveying the emotional weight each of the characters experiences trying to cope with their situation.

4. THE DEPARTED

A star-studded cast rounds out this 2006 Martin Scorsese thriller about the blurry lines between cops and criminals. Two Boston-area natives including Matt Damon and Mark Wahlberg play central roles.

In an effort to combat Irish-American organized crime in Boston, the Massachusetts state police places the young cop Billy Costigan (Leonardo DiCaprio) undercover to infiltrate the crime syndicate run by Frank Costello (Jack Nicholson).

While Billy works to gain Frank's confidence, Colin Sullivan (Matt Damon) an informer for Costello, has infiltrated the state police, rising to prominence in the Special Investigations Unit. Both men become overwhelmingly consumed in their double lives, gathering information for their respective sides.

However when it becomes clear to the mob they have a mole in their gang, Billy and Colin, now in danger of being caught, race to uncover the identity of the other man in time to keep from being discovered.


Tension rides high throughout this film, while Costigan and Sullivan play their games and manipulate both sides. Scorsese keeps viewers on the edge of their seat with the idea that either man's treachery is constantly in danger of being uncovered. It's palpable how much each man's double life takes an emotional toll on his mental stability.

3. GONE BABY GONE

Making his directorial debut in 2007, Ben Affleck helmed this flick starring his brother Casey in the lead role. A native of Cambridge, Massachusetts, Affleck set the film's action in the Boston area.

One of the roughest areas in Boston, Dorchester is not a place for the weak. A four-year-old girl from the neighborhood goes missing but the private investigators Patrick Kenzie (Casey Affleck) and Angela Gennaro are hesitant to take the case.

Pleas from the child's aunt prompt the two to open up an investigation that ultimately puts everything on the line: their relationship, their sanity, and their lives.

Affleck's first time in the director's chair is a positive experience, effectively establishing the type of neighborhood Kenzie operates in, as well as the unconventional tactics needed to find information as a private investigator in an environment like that.


Casey Affleck portrays Kenzie, as a man singularly obsessed with solving the crime, putting everything at risk for the pursuit of truth and justice. Veteran actors Ed Harris and Morgan Freeman bring solid supporting acting to the film.

2. GOOD WILL HUNTING

Even though Matt Damon and Ben Affleck had been floating around Hollywood for a couple of years making movies, they were still considered minor actors before 1997's "Good Will Hunting." The two childhood friends who grew up together in Massachusetts co-wrote this poignant coming of age drama set in Boston.

Working as a lowly janitor at MIT, Will Hunting (Matt Damon) has a gift for mathematics that has the potential to carry him far beyond his working class background. Discovered by a MIT professor looking to nurture his talents, Will learns he must turn his back on his neighborhood and his best friend (Ben Affleck) to achieve academic success.

Will's life becomes further complicated with the introduction of a budding love interest in a wealthy Harvard medical student (Minnie Driver), and the attempted help of a washed-up shrink named Sean Maguire (Robin Williams). Sean grapples with Will to open up and to confront the psychological damage of his abusive upbringing so that he can learn to trust others and to move forward in the next chapter of his life.


Affleck and Damon's screenplay is poignant without being overly sappy, creating believable characters the audience becomes attached to. Robin Williams displays a powerful range of emotions in his character, showing a hardened man capable of giving tough love, yet burdened with grief over the loss of his true love.

1. BOONDOCK SAINTS

When "Boondock Saints" came out in 1999, it largely flew under the radar. I did not hear about the film until 2002. Much like many other people who have become fans of this movie, I saw the film because of word-of-mouth. A friend recommended that I see the movie, since it was one of his favorites.

Two Irish brothers from South Boston, beat up a couple of Russian mobsters in a local bar on Saint Patrick's Day. Embarrassed about being beaten, the Russians come to kill the MacManus brothers in their home. In a daring feat, the two survive, but they kill the gangsters in the process.

Special Agent Smecker (Willem Dafoe), the brilliant FBI agent assigned to the case, figures out the brothers did it, but that they were acting in self defense so he does not charge them for murder.

Sleeping in their holding cell, the religious brothers have a vision of God commanding them to kill evildoers. From there the two decide to dedicate their lives to vigilante justice, killing criminals to make the world a safer place for good people.

Action sequences throughout the film are intentionally epic, using slow motion and intense music to glorify the gunfire and killing. One of the most unique aspects of storytelling in the film that makes it so entertaining, is that audiences see the bullet riddled crime scene aftermath before they actually know what happened.


Willem Dafoe's character becomes more fascinating because his forensic knowledge, allows him to reconstruct the action in his head. It's this action that the audience gets to see as he retraces what happened in his mental picture.

"Boondock Saints" is a low-budget film that feels more grounded in Boston than a lot of movies, because it steers away from some of the more common landmarks, while still reminding audiences they are in the city.

Personally I believe it's a fun action film, that should not be overanalyzed, but it can't help but raise the moral question "Is it right to kill even if it's in an attempt to preserve the public good?"

That wraps up my list of great movies about Boston. One movie I would include as an honorable mention would be the Brendan Frasier movie "With Honors." That's another movie worth checking out.

Did I leave any of your favorite Boston movies out? Are you planning to see the new "Boondock Saints" movie? Let me know.

Evan Crean
Story by Starpulse contributing writer Evan Crean, a movie trivia guru and trailer addict with a practically photographic memory of actors and directors. Get a first look at the movies premiering each week, which which ones will be worth your $10, which ones you should wait to rent and which ones aren't worth your time.



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