For starters, The Town didn't have a particularly good, or believable caste. That's especially true of the leading female star, Rebecca Hall, who played the role of the angelic-looking, coy and weepy princess/queen of a bank manager whose bank was robbed at gunpoint by Doug MacRay and his posse of masked bandits, her assistant manager brutally beaten within an inch of his life, and she ended up being blindfolded, abducted and taken as a hostage by the four thieves/thugs, since she was irresponsible enough to set off the bank alarm, when she shouldn't have.
The beginning of "The Town", with the aerial/on the ground shots of Charlestown and Boston, generally, as well as the opening bank heist, when Claire is forced to open the safe at gunpoint by Doug and his men, who are wearing skull masks and nun outfits, is interesting, but, as a film overall, it began to go downhill in a matter of minutes, at least for me.
Had a somewhat different-looking woman played Claire Keesey the bank manager with a bit more of an "edge", her character, especially when she and Doug MacRay got involved wholesale in a romance, might've been a bit more believable, but that didn't happen.
Not withstanding the fact that Ben Affleck was a little too pretty-boy and too unauthentic-looking to be really believable as a thieving, thuggish Charlestown Townie, there were many Grade B actors/actresses who were either inexperienced, or were thrown in at sort of the last minute, for extras.
I also might add that The Town was not a particularly accurate portrayal of Charlestown. It made Charlestown, and Boston, generally, too pretty and bucolic-looking, considering that the story takes place in a rough and run-down urban area. The Doug-Claire romance (which, imho, took away from The Town considerably), not only lacked real chemistry (The chemistry between Doug & Claire was quite paltry at best, and underdeveloped. They were like two young teens who were starting out on their first romance and were out on their first date.), but it was unbelievable and unrealistic in that, historically, the Town-Gown tensions here in Boston have always been (and still are) too acute for a romance between a Charlestown Townie and a yuppie bank manager realistically possible, especially a Townie who has an extensive criminal record of violent crimes, such as armed bank/armored truck robbery, assault, and, ultimately the committing of murder(s) on top of it all, like his friends/accomplices in crime.
Krista, the slatternly, drug-addicted, drunken sister of "Jem" Coughlin (Doug MacRay's best friend and housemate) who was a drug mule for "Fergie" the Florist who employed Doug MacRay and his men, and slept around town with too many men to make the father of her infant daughter, Shyne, clear, was played by Blake Lively, who, although having a small part in this film, might've been more believable as the messed-up Krista if she'd been more developed in this film, but who knows.
Owen Burke, the guy who played Desmond (Dez) Elden, was pretty much irrelevant through this film. He was a college-educated guy with a decent job and a decent salary, but he was stupid enough to pretty much go for the ride, except for being a little bit of a technical guy whenever Doug and his other men needed him. A case of exploitation, imho.
Jeremy Renner, who played the psychotic "Jem" was a little bit more believable than the rest of them, but he, too, was not a bargain.
I have to admit that I found myself liking and sympathizing with FBI Special Agent Adam Frawley (played by Mad Men's John Hamm), as well as SWAT and the rest of the law enforcement people who were out to bring Doug MacRay and his men down, stop their careers once and for all, and to have them tried for, hopefully charged with their crimes (i. e. armed bank/armored car robberies, assault, murder), and hopefully forced to serve long, hard terms in a Federal penitentiary.
The fact that Doug MacRay followed Claire around, knowing that Jem would probably really go off his rocker and do more harm than good, and then met Claire Keesey "by chance" at a Charlestown laundromat, where, stressed out by the robbery, bursts into tears and joshed by Doug, who tells her some dumb, unfunny jokes, is rather suspicious. This part of the film provides the message that it's okay to stalk somebody like a predator before moving in to really exploit them for their own selfish motives, which is what Doug MacRay did when he sort of secretly tailed Claire and then met her "by chance" in the laundromat, joshed with her to make her laugh, and then asks her out on a date.
The fact that Claire so readily accepted a date with a guy that she'd never even set eyes on, and, unbeknownst to her, had been sort of stalking her, and ends up in a fullscale romance with him, especially since he turned out to be the de-facto leader of the guys who's robbed her bank at gunpoint, abducted her and seriously injured her colleague just days before is rather suspicious, imho.
The car chase/car crash scenes, especially in Boston's North End and Fenway Park, as well as the shoot-outs, imho, were toally unrealistic, as was the setting the vans on fire. How could anybody have really survived those car chase/crashes and shoot-out scenes, not to mention the fire-settings? They couldn't really. There would've been dead, broken bodies all over the place, and there's no way that car-chase scenes/shoot-outs in the North End could've taken place without endangering nearby residents and businesses in the area. Sure, The Town's fiction, but it has to be somewhat believable, which it wasn't really.
What's also hard to believe is how the Boston Cops/FBI and SWAT could get by without making a total bust and having Doug MacRay and his men not only arrested but brought to trial, charged with, and forced to serve prison time.
Yet, it's also true that, while the identities of Doug MacRay and his posse of men were known, no evidence or proof could be obtained, partly due to Charlestown's existing Code of Silence, and partly because Doug and his men had a way of bleaching up the crime scenes to destroy all clothing fibers/DNA so that a match couldn't be obtained, and/or by setting fire to the getaway vans and the switch vans, all in order to destroy any evidence and to (hopefully) throw the FBI and other law enforcement people off their trail.
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