Recently spent a week in Boston and was reminded of (1) The number of contemporary films that use Boston as a setting (2) what makes Boston a unique film setting.
"Recent" films taking place in Boston include Good Will Hunting, The Town, Fever Pitch, Mystic River, Gone Baby Gone, The Departed, With Honors, The Boondock Saints, A Civil Action, Next Stop Wonderland, The Fighter, and much of The Social Network.
Now, certainly actor Ben Affleck & writer Dennis Lehane have something to do with this, but I think there are certain reasons why Boston makes a good film setting.
(1) Accent - An accent can create a "unique setting" in itself, and also some award attention if done right, those Oscar voters love accents.
(2) Visual Striking Neighborhoods - The neighborhoods in Boston all have a unique feel and in the midst of tall buildings, and row houses, you get some crazy angled streets, cobblestone, the bay, the rivers, etc.
(3) A Walking City - This city is a walking city, where private vehicles in the city are more of a nusiance than anything else, so this means you have people interacting in a variety of ways, with limited scenes in cars and private residences.
(4) European Stereotypes - The Italians, the Irish, and the mobs. Watching the news in Boston is sometimes in itself seems like a movie pitch and these European underground society and local pride creates story lines in themselves, as well as unique affiliations and relationships. This also often createes a "gray line" where black and white, good and evil, right and wrong don't seem to be so clear.
(5) Fenway - Fenway Park is a place so unique to Boston - so whether there's an exciting fight scene in Boston (as we see in The Town), or a movie about Boston baseball (Fever Pitch) or even a short trip to the stadium (Moneyball) this setting is unique and can only be shot in one place - Boston.
(6) Colleges, Namely Harvard - There are so many colleges in Boston, and college stories often hit the cineplex - and that's why we see schools like MIT & Bunker Hill Community College in Good Will Hunting, or scenes dealing with Harvard in Legally Blonde, The Social Network, or The Firm.
(7) Multiple Socio-Economic Classes - Look no further than Mystic River, Good Will Hunting, or The Fighter to see that there is definitly room for a variety of social classes in a single film.