Real loss is only possible when you love something more than you love yourself.

Sean

Will: Do you like apples?
Clark: Yeah.
Will: Well, I got her number. How do you like them apples?

My boy's wicked smart.

Morgan

Look, you're my best friend, so don't take this the wrong way. In twenty years, if you're still livin' here, comin' over to my house to watch the Patriots games, still workin' construction, I'll fuckin' kill you. That's not a threat. Now, that's a fact. I'll fuckin' kill you.

Chuckie

I can be in the NBA. I'm tall, I like to wear shorts. Hook! Hook! Dunk! Dunk! Baby, I'm all about three points.

Skylar

If you ever disrespect my wife again, I will end you. I will fucking end you. You got that, chief?

Sean

See you Monday. We'll be talking about Freud and why he did enough cocaine to kill a small horse.

Sean

Skylar: You were hoping for a goodnight kiss.
Will: No, you know. I'll tell ya, I was hoping for a goodnight laid, but I'd settle for a good night kiss.
Skylar: [Bursts out laughing] How very noble of you.
Will: Thank you. But I was, you know, hoping for a good night kiss.

Morgan: Man, I can't believe you brought Skylar here when we're all fucking bombed and been drinking. What the fuck is she gonna think about us?
Will: Yeah, Morgan, it's a real rarity that we'd be out drinking.

Skylar: Maybe we could go out for coffee sometime?
Will: Great, or maybe we could go somewhere and just eat a bunch of caramels.
Skylar: What?
Will: When you think about it, it's just as arbitrary as drinking coffee.

You're sitting on a winning lottery ticket and you're too big of a pussy to cash it in.

Chuckie

And why does he hang out with those retarted gorillas, as you called them, because any one of them, if he asked them to, would take a fucking bat to your head, okay? It's called loyalty.

Sean

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