Top 5 – Movies Set in Boston

With Scott Cooper’s Black Mass, starring Johnny Depp as infamous gangster Whitey Bulger as he runs the streets of Boston in the 1970’s, coming out this Friday, let’s look back at some of the best movies set in Boston.

5- Fever Pitch (The Farrelly Brothers, 2005)

I could have gone with better overall films like the rousing The Fighter (2010), the extremely entertaining The Boondock Saints (1999) or one of the great Paul Newman performances in The Verdict (1982).  But instead, I went with a Farrelly Brother’s romantic comedy starring Jimmy Fallon and Drew Barrymore.  Why you ask?  First, this is one of the Farrelly Brother’s best films and by far their most mature.  Fallon and Barrymore have remarkable chemistry and I actually cared about their relationship and the film is full of heart and laughs.  But the real reason this deserves a spot on the list is because of its depiction of the Boston Red Sox World Series win.  The Red Sox are a staple in the Boston community and at the time the movie was made, the Red Sox had not one a World Series in nearly 100 years.  This films shows the importance of the Red Sox to the city of Boston and shows how monumental of a moment that was not just for sports fan, but for all Bostonians.

4- Good Will Hunting (Gus Van Sant, 1997)

Now we’re on to some all-time greats.  Deciding between these next four was almost impossible, as they all represent Boston perfectly.  So, I decided these on film quality, and these are all amazing movies.  When you think of Boston movies, Good Will Hunting is probably the one that comes to mind.  From the accents to the personalities, this is a truly authentic look at Boston youth.  It is a look at the class lines that famously divides the city as well as an unorthodox underdog story about a troubled genius.  With its great script and direction, along with raw and superb performances, including a never better Robin Williams, Good Will Hunting is an outstanding piece of cinema.  How do you like them apples?

3- The Departed (Martin Scorsese, 2006)

The Departed is brilliant depiction of cops and gangsters in South Boston.  Martin Scorsese’s cat and mouse thriller throws us into the heart of the Boston P.D. and the Irish mafia, as we follow a cop (Leonardo DiCaprio, in one of his best performances) who’s undercover in the mob and another cop (Matt Damon, unlike anything he’s done before) who is actually a mole for the mob.  Add in a sharp script, excellent supporting cast, including Jack Nicholson, Martin Sheen, and Oscar nominee Mark Wahlberg, and some of Scorsese’s best direction, and you get one of the most entertaining, exciting, best gangster films of all-time.

2- The Town (Ben Affleck, 2010)

Boston native Ben Affleck directed and stars in this crime drama that brings us to the crime capital of Boston, Charlestown.  Affleck has made a character driven action movie in the same vein as Michael Mann’s Heat (1995).  Loyalty, brotherhood, and identity are all conveyed by an all-star cast, highlighted by Jeremy Renner as the fiery, quick triggered Jem.  The Town also features some of the best shootouts and realistic action sequences in recent cinema, and gives us one of the wildest heists ever, as the guys attempt to rob the Boston cathedral, Fenway Park.  The Town is a crime classic and shines a light on one of the grittier parts of Beantown.

1- Mystic River (Clint Eastwood, 2003)

Mystic River is one of those movies that sticks with you long after you see it.  It’s a coldhearted, brutal movie about loss, friendship, revenge, and the effects of sexual abuse.  Oscar winners Sean Penn and Tim Robbins and a criminally under appreciated Kevin Bacon, all give career best performances as three former best friends torn apart by tragedy.  This movie shows the the closeness of Boston neighborhoods, and similar to The Departed, shows the conflict between cops and gangsters.  Mystic River is a true cinematic masterpiece and the crowning achievement of Clint Eastwood’s career.

What are your favorite movies set in Boston?  Comment below or hit me up on Twitter @kevflix or on Facebook at Kevflix.