Sean: Thought about what you said to me the other day, about my painting. Stayed up half the night thinking about it. Something occurred to me... fell into a deep peaceful sleep, and haven't thought about you since. Do you know what occurred to me?
Sean: You're just a kid, you don't have the faintest idea what you're talkin' about.
Will: Why thank you.
Sean: It's all right. You've never been out of Boston.
Sean: So if I asked you about art, you'd probably give me the skinny on every art book ever written. Michelangelo, you know a lot about him. Life's work, political aspirations, him and the pope, sexual orientations, the whole works, right? But I'll bet you can't tell me what it smells like in the Sistine Chapel. You've never actually stood there and looked up at that beautiful ceiling; seen that. If I ask you about women, you'd probably give me a syllabus about your personal favorites. You may have even been laid a few times. But you can't tell me what it feels like to wake up next to a woman and feel truly happy. You're a tough kid. And I'd ask you about war, you'd probably throw Shakespeare at me, right, "once more unto the breach dear friends." But you've never been near one. You've never held your best friend's head in your lap, watch him gasp his last breath looking to you for help. I'd ask you about love, you'd probably quote me a sonnet. But you've never looked at a woman and been totally vulnerable. Known someone that could level you with her eyes, feeling like God put an angel on earth just for you. Who could rescue you from the depths of hell. And you wouldn't know what it's like to be her angel, to have that love for her, be there forever, through anything, through cancer. And you wouldn't know about sleeping sitting up in the hospital room for two months, holding her hand, because the doctors could see in your eyes, that the terms "visiting hours" don't apply to you. You don't know about real loss, 'cause it only occurs when you've loved something more than you love yourself. And I doubt you've ever dared to love anybody that much. And look at you... I don't see an intelligent, confident man... I see a cocky, scared shitless kid. But you're a genius Will. No one denies that. No one could possibly understand the depths of you. But you presume to know everything about me because you saw a painting of mine, and you ripped my fucking life apart. You're an orphan right?
Sean: You think I know the first thing about how hard your life has been, how you feel, who you are, because I read Oliver Twist? Does that encapsulate you? Personally... I don't give a shit about all that, because you know what, I can't learn anything from you, I can't read in some fuckin' book. Unless you want to talk about you, who you are. Then I'm fascinated. I'm in. But you don't want to do that do you sport? You're terrified of what you might say. Your move, chief.
Why shouldn't I work for the N.S.A.? That's a tough one, but I'll take a shot. Say I'm working at N.S.A. Somebody puts a code on my desk, something nobody else can break. Maybe I take a shot at it and maybe I break it. And I'm real happy with myself, 'cause I did my job well. But maybe that code was the location of some rebel army in North Africa or the Middle East. Once they have that location, they bomb the village where the rebels were hiding and fifteen hundred people I never met, never had no problem with, get killed. Now the politicians are sayin', "Oh, send in the Marines to secure the area" 'cause they don't give a shit. It won't be their kid over there, gettin' shot. Just like it wasn't them when their number got called, 'cause they were pullin' a tour in the National Guard. It'll be some kid from Southie takin' shrapnel in the ass. And he comes back to find that the plant he used to work at got exported to the country he just got back from. And the guy who put the shrapnel in his ass got his old job, 'cause he'll work for fifteen cents a day and no bathroom breaks. Meanwhile, he realizes the only reason he was over there in the first place was so we could install a government that would sell us oil at a good price. And, of course, the oil companies used the skirmish over there to scare up domestic oil prices. A cute little ancillary benefit for them, but it ain't helping my buddy at two-fifty a gallon. And they're takin' their sweet time bringin' the oil back, of course, and maybe even took the liberty of hiring an alcoholic skipper who likes to drink martinis and fuckin' play slalom with the icebergs, and it ain't too long 'til he hits one, spills the oil and kills all the sea life in the North Atlantic. So now my buddy's out of work and he can't afford to drive, so he's got to walk to the fuckin' job interviews, which sucks 'cause the shrapnel in his ass is givin' him chronic hemorrhoids. And meanwhile he's starvin', 'cause every time he tries to get a bite to eat, the only blue plate special they're servin' is North Atlantic scrod with Quaker State. So what did I think? I'm holdin' out for somethin' better. I figure fuck it, while I'm at it why not just shoot my buddy, take his job, give it to his sworn enemy, hike up gas prices, bomb a village, club a baby seal, hit the hash pipe and join the National Guard? I could be elected president.
Chuckie: I didn't get on Cathy last night.
Will: Why not?
Chuckie: I don't know.
Chuckie: Why didn't you give me none of that nasty little hoochie-woochie you usually throw at me?
Cathy: Oh, fuck you and your Irish curse, Chuckie. Like I'd waste my energy spreading my legs for that Tootsie Roll dick? So go home and give it a tug yourself.