25th Hour (2002)

Naturelle Riviera: One minute ago, you were my friend. Are you drunk? Tell me you've been drinking too much. You're fucking drunk.
Frank Slaughtery: I'm Irish. I can't get drunk, all right? I know exactly what I'm saying.

Jakob Elinsky: What do we say to him?
Frank Slaughtery: We say nothin'. The guy's going to hell for seven years, what are going do wish him luck?

Kostya Novotny: Monty, I have beautiful woman, very nice.
Monty Brogan: Yeah, well, I'm not really in the mood for that. I've got a nice girl.
Kostya Novotny: I know, I know. Tonight is a special night. Last night as free man. I pick her out special, just for you.
Monty Brogan: The last girl you picked out special for me had three teeth, all in the back.

Uncle Nikolai: This is my advice to you: When you get there, figure it out who's who. Find the man nobody's protecting. A man without friends. And beat him until his eyes bleed. Let them think you are little bit crazy, but respectful, too. Respectful of the right men.

Jakob Elinsky: I kissed her.
Frank Slaughtery: You what?
Jakob Elinsky: My student. I, I kissed her.
Frank Slaughtery: Who are you trying to be... R. Kelly?

Agent Flood: Shiiit... Mr. Brogan, I do believe you're fucked... royally! shiiiiit....

Monty Brogan: Champagne for my real friends, and real pain for my sham friends.

Monty Brogan: I need you to make me ugly.

Jakob Elinsky: Jesus Christ.
Frank Slaughtery: Yeah.
Jakob Elinsky: Yeah, the New York Times says the air is bad down here.
Frank Slaughtery: Well, fuck the Times... I read the Post.
Frank Slaughtery: EPA says it's fine.
Jakob Elinsky: Well, somebody's lying.

Frank Slaughtery: You know, you're wearing a striped shirt with a striped tie, you know that, right?
Phelan: Yeah, I do it for the ladies.
Frank Slaughtery: Oh - the ladies ever tell you that you look like a fucking optical illusion?
Phelan: Yeah?
Frank Slaughtery: Go away, disappear... come on.
Phelan: I'm outta here.

Uncle Nikolai: I have been in three different prisons, Montgomery. Three different countries. And you know what I learned? I learned prison is a bad place to be.