Doug is from a poor area of Boston called Charlestown, or simply "The Town" to locals. He and his best friend since childhood, Jem, are bank robbers; together, with two other loyal pals, they rob a bank, take the beautiful bank manager named Claire hostage to insure safe escape, and let her go once they've gone a safe distance. Unfortunately for them, they find out Claire doesn't live far from them, and Jem is concerned that she might have seen their faces. Doug goes to investigate, and while getting to know her and subtly digging for evidence she may know more than she's letting on, he begins to fall in love with her. Once he earns her trust, she tells him that she saw a tattoo-- Jem's tattoo-- and is thinking about telling the police. Doug knows that Jem will kill her if she tells the authorities, so he makes sure she is suspicious of the police in order to keep her from squealing. The FBI comes to town, and due to Doug and Jem's shady past, they immediately begin surveillance on Doug's entire crew. When the head of the FBI investigation, Frawley, finds out that Claire is dating Doug, he tells her that she will be tried as an accomplice for the initial bank robbery. Claire freaks out and immediately dumps Doug, putting Doug in a bad spot-- they're preparing a robbery of Fenway Stadium, and if Claire tells the police what she knows, or if Jem decides to kill Claire, then his life will be ruined.
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Best part of story, including ending:
It's a compelling crime action flick, with some great chase sequences and robberies, but at the heart of it some terrific character relationships.
Best scene in story:
The final robbery of Fenway is as intense as a robbery sequence gets in cinema, with our heroes surrounded with no probable means of escape.
Opinion about the main character:
Doug, despite being a career criminal, has a beating heart underneath it all, and he deeply and genuinely cares about Claire. We feel for his plight.