Damn, is Matt Damon cool in Rounders or what? The guy’s a genius lawyer-to-be kicking ass in the courtroom, but then he returns to his grimy back-room poker roots and gets his hands dirty, just to save an idiot friend Ed Norton who can’t stop cheating and getting beaten up by enormous dirtbags who have offices in basements. Damon doesn’t even need to keep the girl at the end — that’s how cool he is.

Perhaps the ultimate cool-guy Matt Damon scene in Rounders, though, is easy to miss: when Damon, in desperation for a bankroll to take down the evil Russian Oreo-ad underground poker boss John Malkovich, tells his mentor John Turturro about bluffing the best player in the world at the time, Johnny Chan, for no reason other than a weird, sexy twist on the classic badass mantra: because Johnny Chan was there.
This undeniable, gnawing need to force other men to back down using only Jack and Shit as persuasion is why the bluff exists. This doesn’t mean it’s a good idea, especially if you’re going to base all of your poker playing on Rounders, as we are. The idea in Rounders is that Damon might be a better player than Chan, he just doesn’t have the bankroll or the prestige. This makes bluffing the perfect, coolest way to win. Because that’s all we really want, isn’t it? To bask in a little Matt Damon poker badassery?
1 Play poker. In Damon’s Rounders story, he’s in a casino, but look: you don’t have that kind of cash to blow right now. You’ll get your enjoyment out of the mad-rush bluff because you’re beating your friends, not because you’ll be able to buy a new Toyota Camry with the winnings. Also: you know how to play poker, right?
2 Know who Jonny Chan is. Not, like, the actual Johnny Chan. He is the champion WSP player. No, the Johnny Chan you’re looking for is the hotshot player at your table. He has a lot of chips, a lot of swag, and he’s likely wearing sunglasses. And you’re going to kick his ass. In poker.