I spent three years in the Boston area (Cambridge to be precise) and got a decent feel of the city while I was there. These weren’t my favorite years, and frankly I had more fun in three months in New York City than I had in three years in Boston.

Boston is a provincial place, but you can’t deny it has character. Also, it’s such a beautiful city, and even the shitty parts have a vibe that comes across on the screen.

I recently watched “The Town” for the first time, and I wondered why we needed so many movies about Boston. Then, when listening to The Rewatchables podcast for this film, Bill Simmons asks the question about the best Boston movies. This isn’t a surprise, since Simmons loves lists almost as much as he loves Boston.

But, as usual, he comes up with pretty good lists . . . and he nailed it with his Boston list. And since I agree with it, here’s my take on those best Boston films in no particular order:

The Verdict

Screenshot The Verdict Paul Newman and Charlotte Rampling

This movie made a real impression on me when I was younger. I wanted to be a lawyer, and “The Verdict” captured the drama of arguing the ultimate case . . . perhaps too well, as the law in real life is much more boring and far less dramatic. But these are the types of cases lawyers live for. Paul Newman is brilliant in this film as the broken down lawyer who finds redemption. Meanwhile, the backdrop of Boston, with all its history and tradition, provides the perfect, romanticized setting for an epic David vs Goliath legal battle.

The Town

Screenshot The Town

As pointed out in The Rewatchables, there are so many aerial shots of Boston in this film. Everything about this film feels authentic, from the casting to the accents and all the locations. Of course, it may not be true that the Charleston neighborhood is the bank robbery capital of America, but that really doesn’t matter. Throw in some of the best car chase scenes we’ve seen in years and you have a killer Boston movie.


Screenshot Spotlight

The Catholic Church is so ingrained in the culture of Boston, making the exposure of the priest scandal by The Boston Globe that much more shocking and dramatic. This film captures all of that so well, particularly the contrast between the powerful, elite class surrounding Cardinal Law and the working class families victimized by the priests and the church.

The Departed

Screenshot The Departed

The film opens with a badass song by the Dropkick Murphys . . . everything after that is just gravy.

Good Will Hunting

Screenshot Good Will Hunting Matt Damon

Working in the Carlton Fisk home run in the 1975 World Series cemented the Boston connection in this excellent film . . .