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I think that The Town is a good example of a film with a lot of promise, much advertising, and potential, which started out as being pretty good, but then went steadily and rapidly downhill (for me, anyhow), after the first bank heist.
How I wish there'd been a better cast, less emphasis on the Doug-Claire romance and more emphasis on the heists, and that the characters overall had been better-developed.
How I wish that Doug and Claire had gotten punished for their arrogance and wrong-doings; Doug being sent to serve a long, hard term in a federal penitentiary for his crimes (i. e. armed robbery, murder, assault, kidnapping), and Claire being criminally prosecuted herself, or put on some sort of probation for lying to the Feds about who Doug was (the leader of the band of Townie guys who robbed her bank at gunpoint, blindfolded and kidnapped her after beating up and almost killing her assistant manager for nothing), and about not having seen Jem's "Fighting Irish" tattoo on the back of his neck, and for tipping off Doug to the Feds' presence in her apartment right when they were on the verge of catching him, therefore allowing him to go free and elude the law, for receiving stolen goods and using that money for a presumed charity ( the restoration of a hockey rink), instead of anonymously turning it into the police/authorities.
Better still, The Town would've been an excellent movie if it had been about Doug MacRay's becoming an all-out professional hockey star, thus beating the odds of growing up in a disfunctional family and not following in his father's footsteps and becoming a professional armed bank robber and a murderer.
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"It does not take a majority to prevail, but rather an irate, tireless minority, keen on setting brush fires of freedom in the minds of men." -- Samuel Adams (1722-1803)