“- 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

“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

When we lose, that's another story. I'm talking about the kind of loss that makes your asshole pucker to the size of a decimal point. You've just recreated the worst possible nightmare this side of malignant cancer and you're standing there and you suddenly realise "Hey, I'm still here. I'm still breathing. I'm still alive".

Al Pacino - Walter

“- Curtis: Next time you quit when I say it's time.
- Gerry: Some guys are born to lose.”
Ryan Reynolds - Curtis
Ben Mendelsohn - Gerry

“- Kate: You lost your birthright... in one hand of poker.
- Luc Teyssier: I'm an asshole, what can I tell you?
- Kate: Uh-huh. So that's why he hates you and you hate him.
- Luc Teyssier: Oui... that and I slept with his wife.”

Meg Ryan - Kate
Kevin Kline - Luc Teyssier