Picking my favorite film that is set in Boston is a tough call, but I think I am going to have to go with The Departed (2006) directed by Martin Scorsese (his only Academy Award win) and starring an all star cast with Leondardo DiCaprio, Matt Damon, Jack Nicholson, Alec Baldwin, Mark Wahlberg, Martin Sheen, and Vera Farmiga. This film captures the element of the the culture of a changing Boston throughout the decades and the evolution of the mafia and the way business is conducted. The film uses the beauty of Boston so well, and the entire back drop of the film is escaping the where you born. DiCaprio's character is born in South End and he is referred to as a "Southie" several time in the film. The Departed also takes an interesting look at the Irish mob and how this intertwines within the cities culture. This is hands down one of my favorite mafia movies, and when I think about Boston this movie is prevalent on my mind.
The next film I think about also involves Matt Damon and that is the film Good Will Hunting (1997). Gus Van Sant directs the film about a janitor at Harvard from the South End of Boston who is smarter than most of the people at the school. Damon's character Will has never had the opportunity to rise above where he was born and become something more. One day Will solves an impossible math problem on chalkboard and the professor of the class wants to harness his potential. With this Will meets Sean Maguire (Robin Williams) and he works out his own personal issues. Will also meets a girl named Skylar (Minnie Driver) and he starts to want to change because to be with her he has to be something more. The screenplay for this film was written by Matt Damon and Ben Affleck and who knows Boston better than these two men. They grew up in this city and weave a fairytale story about the place they were born, and do so with a lasting impression.
Speaking of Ben Affleck, this man's directorial prowess has impressed me; has undertaken two films (both set in Boston) Gone Baby Gone (2007) and The Town (2010) and done a great job using his own understand of this city to unravel stories about Boston. Gone Baby Gone focuses on Patrick Kenzie (Casey Affelck-yes Ben's brother) a cop in Boston trying to find a missing girl. The film is based the Dennis Lehane book, and Affleck uses the material of Lehane well and captures the interaction between the different elements of Boston well. The Town is Affleck's best work to date and his homage to the city of Boston (forget that the city was pist your filming there shut down a lot of the city) in the end the film speaks for itself and Affleck knows and understand how to use this city to make a quality film. The Town focuses on the intersection of crime in Boston and taking down people who give the city a bad name. I have to praise Affleck because he knows his stuff, and the fact that he knows this city so well plays to his strengths as a director.
Another adaptation from a Dennis Lehane book is Mystic River (2003). This film also centers around a missing girl who is found dead, but it also centers around three friends who grew up in Boston and all ended up in different places and their lives were changed because of one event. Clint Eastwood is another brilliant director who filmed in Boston and used the city to help set the stage for this film. Boston is not the star of this film, but it acts as wonderful setting that helps espouse terrific storytelling, and great acting surrounding the culmination of all the events that take place.
So after looking at all of these films set in Boston, it made me think-wow is this city all about crime, the mafia, and tragedy? I then asked myself one question, what do the people of Boston love most, and the answer was simple-the Red Sox! The not-so-great film Fever Pitch (2005) highlights one of Boston's favorite things. The ending had to actually be re shot because the Red Sox won the World Series that year. The details of the film are not important, but the one character Jimmy Fallon plays loves the Red Sox so much it almost interferes with a new relationship. This is by no means a classic, but to the people of Boston it is a love letter to their team that struggled so much to triumph in the face of their struggle to win a World Series, and that is what Boston is all about.
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