Will: Whoa, hold it, man. Come on, there's an old gambling superstition. It says that if you walk into a casino backwards you'll have good luck.
Carlton: Will, you poor public school casualty. Everyone knows there is no such thing as luck. There's only the astute mastery of probability.
Will: Have it your way, man.
[As Will walks into the casino backwards, Carlton is distracted and crashes into a waiter]
Will: Wow, you know, Carlton, you are lucky. That could have been an asteroid.

Brett: You know, I hope you don't mind my saying it, but you sure look good. How was Heaven when you left it?
Vivian: [giggles]
Philip: Anybody ever tell you, you sure look sexy when you deal?
Brett: We all have. We're not here because of the way she shuffles cards, you know what I mean?
Philip: Gee, it's chilly in here. I'd hate for my wife to catch cold.
[After Phil drapes his jacket over Vivian, the men at her table walk away]

Will: Come on, don't act like you never done it before. [Mrs. Pullman blows on his dice]
All right, my lucky drawers is riding high, put your money on me or kiss it goodbye! Just like it's supposed to be! Give it to me again. Can I get an amen?
Brett: Amen.
Will: Yes, sir. All right.
Carlton: Will, please, the book says there's no way you can win. If I were you, I wouldn't touch those dice.
Mrs. Pullman: Posse out, short stuff. Robin's on a roll.
Will: All right, here we go. Hoagies, cheese steaks, chicken on a spit, seven come eleven 'cause I'm too legit to quit!

Geoffrey: Two pairs, kings and queens.
Ashley: Three aces. Sorry, Geoffrey. You're $94 in the hole. Should we play again?
Geoffrey: I think not.
Ashley: Are you mad at me?
Geoffrey: Of course not, Miss Ashley. You play very well. Where did you learn? A back alley in Calcutta?

Crowd: [singing] Go Will, Go Will, Go Will...
Carlton: Will, you're insane. Quit while you're ahead.
Will: Yo! Man with the bald head. Yo. Tell me what they said!
Mr. Cummings: Seven!
Will: Go Will.
Crowd: Go Will, Go Will, Go Will...
Will: Here we go! Here we go! Eleven! Hey! Now, who's hotter than Madonna in a pointy bra?
Crowd: You are!
Will: Just checking!

Mr. Cummings: May I have everyone's attention, please? It's time for the raffle. A cash prize of $1,000. And the winner is number 10225.
Carlton: [gasps]
Hilary: Carlton, did you win?
Carlton: No, I didn't play and 10225 is my lucky number.

Ashley: Honest, Geoffrey, it'd make me feel a lot better if you'd just take your money back.
Geoffrey: No, thank you. A gentleman always accepts his losses gracefully.
Ashley: Okay, Geoffrey, but you're sure we're still friends?
Geoffrey: Of course, Miss Ashley. [faint smile]

Will: Okay, I just don't understand why you're making such a big deal about this money. I mean, it ain't like I took the Benz drag racing down Sunset at 4:00 in the morning.
Carlton: Tattletale.
Philip: Will, I'm making a big deal because every year the club picks a charity and donates that money to that charity.
Will: But, Uncle Phil, look, if it's supposed to be my money how come I can't do what I wanna do with it? And I don't wanna donate it to the L.A.P.C.
Philip: Will, donating that money is a tradition and a tradition isn't something to be thrown away on a whim.
Will: Whoa, hold up. You calling a red leather suit with matching seat covers a whim?
Philip: Will, you're being awfully selfish. Obviously, you haven't learned a thing since you've been here. We've all been blessed. And donating to someone less fortunate than yourself is not an option, it's a responsibility.
Will: I hear what you're saying, Uncle Phil, you're right.
Philip: Keeping money that isn't yours is wrong. Very, very wrong.
Ashley: I know. I know.

Will: Hey, Ashley, honey, what's up?
Ashley: Would everyone just get off my case? I want to give him the money back, but he won't take it.
Will: Whoa, puberty's in the house.

Ramon: Hey, you looking fine today.
Will: Thanks I did a little something different with my hair.
Ramon: Hey, here's your boom box. I re-wired it. It works fine now. You owe me 50 cents.
Will: Man, 50 cents? That's real reasonable.
Ramon: Hey, a happy customer is a loyal customer.
Will: How much for the shoe shine?
Ramon: $150. Hey, I gotta make up the differences somewhere. How else am I gonna get to basketball camp?
Will: All right, well, hey, let's just get out of here before Linda Blair's head starts spinning around.