Surveillance Guy: Who the fuck are you?
Dignam: I'm the guy who does his job. You must be the other guy.
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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Revealing: When Costello's men drive off, after throwing Queenan off the top of the building, the state troopers are firing at the van. One back window is shot out, then in the next shot of the van the other window is shot out and then the same one is shot again so the one window is shot out twice in the same scene.
Continuity: When Costello and French encounter the cops, the first shot shows the cops' car turning their lights on. In a new shot a second afterwards the lights on the middle and right side cars are out and they are turning them on again. On yet another new angle, the lights on the car on the left turn from off and on again in a split second.
Continuity: In the scene after Queenan dies, when Sullivan picks up his phone, the number Sullivan calls Costigan in isn't the same as the one from which Costigan calls back, even though it's the same mobile (silver and blue vs. Costigan's red phone for Costello's gang). When Sullivan calls, the number begins with something like "617-854" and when he sees Costigan calling back, it's "617-177".