The movie isn’t about you, it’s about Chuckie and Will, and their relationship to the city. For them it isn’t all Boston.

Tufts is in Medford, and maybe partially Somerville. I don’t think any of it is in Cambridge.

Allston pokes into Cambridge. Cambridge surrounds Allston. West of Cambridge is Arlington, Watertown or Belmont. Southwest of Cambridge is still Watertown.

As for Bunker Hill, Somerville is North-East of Cambridge. Only a tiny slice of Cambridge connects to Bunker Hill. The rest of the North-East border is all Somerville.

Boston is South-West of Cambridge, that’s the real story. It surrounds part of it on 1 side in one area because the Charles river curls around Cambridgeport, then it curls the other way and Cambridge surrounds part of Allston.

It has been a while since I watched the movie. But, consider the scene at the beginning where Will shows off his intelligence in a bar. I think the movie set that up as Will and his friends wanting to take a “field trip” to a non-Southie bar. It felt like they were far from the place where they belonged, even though it might have only been a 15 minute drive.

In any case, it isn’t just about leaving Southie. Like I said, at no point does Chuckie say “you’ve gotta get out of this town”. He just hopes that one day when he goes to knock on Will’s door, Will isn’t there. And, it isn’t because he wants Will to move to “a different town”, or something. It’s that he wants Will to not get stuck in a rut, never taking a chance on life, and not using his talents.

Will answering his door whenever Chuckie knocks doesn’t just mean he’s still living in Southie. It also means that he is probably still working the same job, still hanging out with the same people, still in the same rut.

Which 3 sides?

Also, the most famous of those universities (MIT and Harvard) are in Cambridge.

Someone from outside Boston might look at the entire metropolitan area and call it “Boston”, but one of the key elements of the movie is that Will and Chuckie are locals who are living their entire lives in a small neighbourhood in South Boston.

For a local, there are huge differences between Cambridge, Somerville, South Boston, the North End, Beacon Hill, Charlestown, East Boston, etc.

In any case, in the movie he never says “you’ve gotta get out of this town and make something of yourself”. What he does say is that the best 10 seconds of his day is when he walks up to Will’s door and hopes that he’ll have left without saying goodbye. That does suggest that to fulfill his potential he’ll have to move somewhere else, at least for a while. But, the way the lines are delivered, it’s not that he has to leave the Greater Boston Area, but that he can’t just get stuck in a rut, living in the same place, doing the same thing, never taking a chance to improve his life.

Sure, theoretically Will could live in the same house for the rest of his life, while also making the most of his talent by working at Harvard or something and just commuting from South Boston. But, the other context for that scene is the girlfriend.

Chuckie asks Will about his girlfriend, and Will says she’s moving to California to go to med school. That’s what kicks the whole scene off. The audience knows that Skylar invited Will to come with her, and not only did he turn her down, he basically had a panic attack at the idea of leaving his life in South Boston. Chuckie knows Will well enough to know that it wasn’t just a casual fling, and he’s happy to end it because she left town. At the end of the movie, Will’s friends give him a car for his birthday, and he uses the car to drive to California to be with Skylar.

Now, maybe in 10 years he’ll move back to the greater Boston area, get a job at MIT or Harvard, buy a house next door to Chuckie and commute to his job from his old neighbourhood. Maybe his and Skylar’s kids will play little league games together, and the two will hang out to watch the Patriots (and they’ll be in for a hell of an era for that team). But, even then, he’ll have done what Chuckie wanted and not waste his talent.

The scene has nothing to do with leaving the Boston area to get a good intellectual job, and everything to do with not getting stuck in a rut, being scared to take a chance and use your talent.

Which 3 sides? To the North-East of Cambridge is Somerville. To the North is Arlington, to the West is Belmont and Watertown. Boston is basically only to the South-East.

No, Cambridge isn’t Boston.

Cambridge is very close to Boston, but it’s a different city. They’re on opposite sides of the Charles river. These days the river is very narrow (it used to be a lot wider in colonial times, but they’ve drained swamps and built over them since then). The two cities have integrated mass transit systems, and it’s a short walk across one of the many bridges to go between the two.

But, they’re not the same city. The two places have different characters. Boston has “Southie”, the Red Sox, the Celtics, the Bruins. Cambridge is much smaller and has MIT and Harvard. It has no sports teams (other than the school teams) and is a very rich and diverse city because of those rich and diverse schools. Politically it is very different from Boston. People jokingly call it the People’s Republic of Cambridge because even by Massachusetts standards it is very left leaning.

MIT and Harvard are in Cambridge, Massachusetts, which is a different city on the opposite side of the Charles river.

But at age 90, it’s something like a 1 in 4 chance you’ll die every year. So, even if he’s only 9 years older than Stewart, the odds of him outliving Stewart would have been pretty low, all other things being equal.