Top 5 Favorite Boston Films

This time of year, Boston has some of the most breathtaking fall foliage. With cool air moving in and the heat of summer moving out, here’s a spotlight on some of my Boston favorites.

THE TOWN (2010)
This is the newest film on the list. Ben Affleck and Jeremy Renner star as two baddies who are always one step ahead of the law. When a bank robbery goes somewhat awry, they kidnap the female bank manager and Doug MacRay (Ben Affleck) later befriends her. As Doug develops feelings for Rebecca Hall’s character Claire, the FBI is closing in on him and his team of ne’er-do-wells. The casting in this film is superb and the dialogue all feels authentic. This film is not just an action flick, it delves a little deeper into the lives of the characters and the events that guide their decision making.



THE BOONDOCK SAINTS (1999)
This is a great film that was initially a flop. Two brothers are going through life in Boston when they suddenly realize the evilness of the men around them. They decide that it is their Christian duty to rid the world of these criminals. So the two brothers go on the hunt after the city’s most infamous men. All the while, being pursued by a cunning FBI agent played by Willem Dafoe. This film does a great job adding humor into an otherwise very serious film. Every scene has action, humor, or drama, and sometimes all of the above.



THE DEPARTED (2006)
This is the big one on the list. Directed by Martin Scorsese and recipient of four academy awards, this film chronicles the struggle between the Boston police and a crime kingpin. The thing that sets this film apart from so many others is the depth of the script. Each side has a mole working in the other side. The film shows the way these groups interact and the sometimes very difficult choices that must be made. Jack Nicholson, Leonardo Dicaprio and Matt Damon all deliver stellar performances. If you haven’t seen this film, you’re really missing out.



GOOD WILL HUNTING (1997)
This is the only film on the list not involving crime of some kind of crime. Matt Damon is a blue-collar man working as a janitor at MIT. One day he comes across a difficult problem on the chalkboard and decides to solve it. Turns out Damon is a secret mathematical genius but he also has some legal troubles. To avoid jail time he must work with a professor in mathematics and also attend therapy. After a lengthy struggle to find a therapist, he is eventually brought to Robin Williams and the two delve deep into each of their lives. This film does a better job than any other in aptly depicting the lives of some young men from Boston, in that way, this film is a great character study.



THE BRINKS JOB (1978)
This is one of my personal favorites but it’s not particularly well known. With the cast headed by Peter Falk (of Columbo fame) and Peter Boyle, this film sets to recreate the infamous Boston robbery of the Brinks building where $3 million was stolen. This film has some comedic moments as well as a compelling drama-based plot. The acting is what really sets this film apart. The characters are never fully developed and some of the scenes feel forced, but the actors make it seem natural and deliver some great one-liners that give you a chuckle during key moments. This film received a nod from the academy for best art direction and that makes sense because the visuals are done well. If you haven’t seen this, it’s worth checking out but it’s a love it or hate it kind of film.