“- Henry 'Razor' Sharp: Didn't you lose twenty thousand dollars betting here?
- Billy 'The Kid' McDonnen: Yeah, well, who loses the SuperBowl four times in a row?”

Sylvester Stallone - Henry 'Razor' Sharp
Robert De Niro - Billy 'The Kid' McDonnen

“- Jack Fuller: If you stop betting, you never have to lose.
- Joy McNally: I'd bet on you, Jack.”
Ashton Kutcher - Jack Fuller
Cameron Diaz - Joy McNally

“Oh, I don't lose. People who bet on me to lose lose. And they lose big.”
Al Pacino - Willy Bank

“Most gamblers, when they go to gamble, they go to win. When we go to gamble, we go to lose. Even when we win it's just a matter of time before we give it all back.”
Al Pacino - Walter

“In the casino, the cardinal rule is to keep them playing and to keep them coming back. The longer they play, the more they lose, and in the end, we get it all.”
Robert De Niro - Sam "Ace" Rothstein