Top Gambling Scenes in Movies

by Daniel Bennet

Gambling is an eternal source of Hollywood inspiration. Huge risks, cunning strategies, and seemingly impossible wins all make for edge-of-your-seat entertainment.

Unless you’re fortunate enough to hit it big though, playing the odd game of poker, blackjack or keno online is probably not as dramatic. Gamble movies show us what it’s like to be a high-roller, a low-baller, and everything in between.

If you want to relive iconic casino moments or learn about new ones, check out the top gambling scenes compiled by our expert, Daniel Bennet.

Rounders (1998) - Chew Those Oreos

Matt Damon, John Malkovich and Edward Norton star in what seems to be a cautionary tale. As it turns out, the movie is more about compulsive gambling without consequences. Still, it’s as awesome as it is absurd, with some intense moments at the poker table.

Mike McDermott (Damon) promises to quit the game after losing his entire $30,000 bankroll in a poker round. Cue the shady friend’s gambling debts and bad influence (Norton) throw in a Russian Mobster (Malkovich), and our protagonist is back to his old ways. In the end, he pursues his dream of winning the World Series of Poker.

Arguably, the movie’s best gambling scene is during a round of Texas hold ‘em between Mobster Teddy KGB and McDermott. After some taunting, Damon’s character decides to stake all of his money.

It seems like a bad move as his bankroll continues to dwindle. All the while, Teddy KGB smirks as he eats his Oreos. Suddenly, something clicks, and McDermott realizes the Russian Mobster’s “tell.” He goes on to say:

“And usually I would've let him go on chewing those Oreos till he was dead broke. But I don't have that kind of time. I've only got till morning.”

Interestingly, the jury is still out among poker enthusiasts as to what exactly the “tell” entails. Some say it’s how Teddy splits the cookie, while others think it’s whether he eats the Oreo or not.

Ocean’s Eleven (2001) - The Ace is High

Remaking the original 1960 film starring The Rat Pack couldn’t have been easy. However, with an ensemble cast, including George Clooney, Julia Roberts and Brad Pitt, the movie bagged a whopping $450.7 million at the box office.

A gang of talented misfits led by Clooney’s Danny Ocean and his partner-in-crime, Pitt’s Rusty Ryan, plan an intricate heist. They hit three casinos and settle a few scores at the same time. It’s an epic movie filled with camaraderie, swagger, and Las Vegas charm.

We’re introduced to Ocean and Rusty’s dynamic in a gambling scene awash with so many subtleties that it still sparks debate today. Ryan is teaching a group of actors how to play poker when Danny shows up out of nowhere and joins in on the game.

Rusty uses it as an opportunity to explain the art of bluffing. He’s apparently convinced that Ocean is deceiving the table, who is raising the stakes every round. Citing his friend’s hand as a probable pair of face cards, and not much else, Rusty stays in the game.

Surely enough, his students follow suit. Call after call is made as the pile of chips grows larger. Eventually, Ocean nonchalantly shows his hand as he says he’s “not sure what four nines do, but the Ace is pretty high.”

Whether this gambling scene is about Ocean always getting the best of Rusty or if it’s more nuanced than that, nobody really knows. However, some believe the glance at the end proves that the pair actually swindled the rest of the group.

The Hangover (2009) - The Joker and the Thief

This comedy starring Bradley Cooper, Ed Helms, Zach Galifianakis and Heather Graham became the tenth highest-grossing film of 2009. It even resulted in a trilogy, although the second and third instalments received mixed movie reviews.

Four friends head to Vegas for a bachelor party weekend, but things go awry after Allan unwittingly spikes everyone’s drinks. The next morning, they can’t find their friend, Doug, nor can they remember anything. A series of wacky and hilarious events follow as they search for the last member of their ‘Wolfpack.’

The Hangover casino scene is a comical rip-off of the one in the 1988 movie Rain Man. When the gang needs $80,000 to get Doug back, oddball Alan suggests they hit the blackjack tables. He holds up a card-counting book he read on their way to Vegas.

They descend into the casino lobby looking suave, and Allan watches the cards intently as complicated equations encircle his head. A time-lapse montage shows the chips stacking up, accompanied by Wolfmother’s song, The Joker and the Thief.

The gang quickly disappears when pit bosses start looking suspicious. However, it’s a common misconception that card-counting is illegal when really, it’s just frowned upon.