1. Good Will Hunting (1997)
2. The Town (2010)
3. Gone Baby Gone (2007)
4. Mystic River (2003)
5. The Departed (2006)
Contributed by: Spencer
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1. Good Will Hunting (1997)
2. The Town (2010)
3. Gone Baby Gone (2007)
4. Mystic River (2003)
5. The Departed (2006)
Contributed by: Spencer
Shadows & Noise 
No love for Legally Blonde?
It received consideration. For the record, Fever Pitch did not.
What’s the case for Mystic River over The Departed? Is it more “Boston” than I realized?
Exactly. The Departed gets a lot of things right, and to many people, it’s the definitive Boston crime movie — but it still feels like an outsider’s take on the city. They filmed in some of the right places to let you know they were really there (the Zakim Bridge, the State House, Southie, Chinatown, Charlestown), but other than hitting you in the face with some strong accents (and, um, Jack Nicholson’s take), they didn’t really capture the spirit of the city. It was like they were trying too hard.
Mystic River is more authentic. They filmed in the right neighborhoods — Jamaica Plain, Dorchester, Chelsea — and really captured the blue-collar feel and the pervasive, wounded sort of tough-guy psychology of the people who grew up there. Of course, it was written by Dennis Lehane, who is from Dorchester, so it benefited from an insider’s perspective. He wrote Gone Baby Gone, too, and I think that one’s even better at distilling the spirit of the city. It would’ve gone into my number two spot if not for the Fenway Park and North End scenes in The Town. (Though any bank robbers that would think they could make a car getaway out of the North End couldn’t possibly be locals….)