This was a pretty awesome movie. I've seen some folks say they wish it had just been an action thriller, without the "trying to be a better man" plot, but that plot was kind of the point. The story is set in Charlestown, Massachusetts - a working class subset of Boston. Charlestown is heavily populated by people who make their living robbing banks, and the trade is very often passed down through generations. You get the idea that being born into Charlestown is a trap, and that it's near impossible to get out. Doug McRay (Ben Affleck, who also directs) is the ring leader of a particularly successful robbery crew - they've done four armored cars and two banks. They report to "The Florist" (Pete Postlethwait), who is the guy who really runs shit and tells them what jobs to pull. Meanwhile, an FBI agent, Adam Frawley (Mad Men's Jon Hamm), is trying to bring down McRay's gang, with the help of a witness/hostage from their most recent robbery, Claire Keesey (the always amazing Rebecca Hall).
Things start to go screwy Doug introduces himself to Claire as just another guy and falls in love with her. He wants out of the life, but his best friend and partner in crime James (played by The Hurt Locker's Jeremy Renner) is reluctant to let him go. "The Florist" is even more reluctant to do so. Doug belongs with them, period, and they're not going to let him walk out on them.
There are loads of great character dynamics at play here, and both those dynamics and the general story remind me of Michael Mann's brilliant film Heat. Affleck, Hamm, and Hall all bring their A-game, but I found myself even more impressed with Jeremy Renner and (wait for it) Gossip Girl's Blake Lively, who plays James's sister and Doug's sometime girlfriend, Krista. James is a tough guy, and it shows on Renner's untypically weathered face, but you can't help loving his affection and loyalty for Doug. In one of my favorite scenes, Doug asks for James's help - he's found out that some thugs have threatened Claire while she walked to work and he wants to take James with him to kick some ass. Doug doesn't tell James what is really going on and asks his help on the understanding that he can't ever ask about it, and James amusingly agrees. It's a great little relationship moment, but it's also a specific character moment for James, to show us what a violent person he is and that he really doesn't care about "who"s or "why"s - he just likes to make people hurt.
I was pleasantly surprised by Blake Lively, though. Krista starts out as a kind of generic trashy, drug-addicted girl with cheap pick-up lines. She has a kid which may or may not belong to Doug (he claims not), and while you get the impression that she sleeps around a lot, she claims a kind of ownership over Doug and does not like it at all when he expresses his intention to beat a path out of town with someone else. Frawley uses this to his advantage, and while I hated that this had to happen, I still felt sorry for Krista.
The movie ends as satisfyingly as it can, and there's a certain inevitability about it, which I think ties into the theme of inescapability rather nicely. I don't know that it's better than Affleck's other directorial effort, Gone Baby Gone, but I like The Town immensely.