In the scene where Costello is smashing Billy's hand with the boot heel, you can tell from the position of Billy's arm that Costello is hitting the pool table rather than Billy's hand. He is actually hitting his own hand more than he could possibly be hitting Billy's. See more...
The title track to the movie, which plays at the menu and twice in the movie, is "I'm Shipping Up to Boston", a hit song by the Dropkick Murphys. The Dropkicks are a Boston-based Irish band, fitting for a movie about Irish mobsters in Boston. The song is also the entrance music for Red Sox closer Jonathon Papelbon. See more...
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Surveillance Guy: Who the fuck are you?
Dignam: I'm the guy who does his job. You must be the other guy.
Colin Sullivan: I'm going to need the identity of your undercovers.
Dignam: Blow me, alright? But not literally, though. Unfortunately, there's no promotion involved for you.