- Tension breakers are few but quite welcome. They're mostly provided by Dignam.
Dignam: This is unbelievable. Who put the fuckin' cameras in this place?
Police Camera Tech: Oh! Who the fuck are you?
Dignam: I'm the guy who does his job. You must be the other guy.
- During Sullivan's first meeting with Queenan and Dignam:
Queenan: Congratulations on passing the detectives' exam, and welcome to the Special Investigation Unit.
- Costigan witnesses a Sikh shopkeeper nonchalantly respond to a couple Providence mafiosos pitifully trying to shake him down.
Mafioso: I cannot do this anymore. Please don't let me go back empty-handed. Please don't do this. I want to help you.
Shopkeeper: Come to my store next Friday, I'll give you the money.
Mafioso: This is Friday, Babu.
Shopkeeper: You keep on calling me "Babu". It's Singh, motherfucker.
Mafioso: I'm trying to help you.
Shopkeeper: You keep telling me I'm your friend. You don't even know my fucking name.
- Ellerby to Sullivan (without a pause and in a jocular, good natured tone)
"I'm gonna go have a smoke right now. You want a smoke? You don't smoke, do ya, right? What are ya, one of those fitness freaks, huh? Go fuck yourself."
- Ellerby through the whole scene is pretty hilarious. When talking about nabbing Costello, he grabs his crotch as he says "...and he are going to get him!!!!" Also, during the Chinese exchange, Ellerby is excitedly shouting "PATRIOT ACT!!! PATRIOT AAAAAAACT!!!!! because of the surveillance now allowed. Double points for it coming from unabashedly liberal Alec Baldwin.
Dignam: This shithole has more fuckin' leaks than the Iraqi navy.
Ellerby: Go fuck yourself.
Dignam: I'm tired from fuckin' your wife.
Ellerby: How's your mother?
Dignam: Good, she's tired from fuckin' my father.
- Sullivan goes to meet with Frank in a porno theater (with Costigan attempting to tail him). The guy sitting in front of his is obviously masturbating, and getting louder. Just as it sounds as if he's about to cum, he stands up and shows his dick to Sullivan... only for it to turn out to be Costello with a black flesh-colored dildo sticking out of his pants!
- The cranberry juice scene. Just sheer shocking brilliant comedy.
Man: Do you have anyone inside Costello's organization now?
Dignam: Maybe. Maybe not. Maybe fuck yourself.
- After Barrigan shows up and saves Sullivan's ass, Sullivan looks at him and then, almost innocently, blows his head off.
- The "F*ing Short Version" of the movie. Even when trimmed down to nothing but the various F-Bombs in the film, it is still nearly three minutes long.
- The guy throwing the toy duck at Costigan.
- Costigan kneecaps a criminal
I thought you were supposed to go into shock! I'm not in shock! It fuckin' hurts!
- The lecture about dumping bodies in the marsh from Costello to Fitzy.
Costello: Are you soft, Fitz? When I tell you to dump a body in the marsh, you dump him in the marsh. Not where some guy from John Hancock goes every Thursday to get a FUCKING BLOWJOB!
- Fitzy has a spot of black humor after they kill Queenan: "That cop was tough. We were excessive with the cop."