Top 10 Movie Gamblers

Good movies are all about tension. And gambling has always been a great way to introduce tension in spades.

There’s something about high stakes and the chance of loss that gets our adrenaline pumping. And the flawed but likable characters in these kinds of films make us want to root for the underdogs. Whether they are heroes or villains, it is easy to appreciate characters who literally battle against the odds.

Here at The Game Day Casino, we put together a list of our favorite gamblers as seen on the big screen. Let’s dive in.

10. James Bond in Every 007 Movie Ever

The most legendary gamblers are known for staying calm and collected under pressure, and no one in film does that with more poise than James Bond.

Although he has a well-known penchant for casino gambling, Bond takes his biggest risks when he outmaneuvers and outwits villains who are as crafty and resourceful as he is. James Bond is the epitome of keeping your cool despite the odds and deserves to kick off our list.

9. Johnny Hooker in The Sting (1973)

Johnny Hooker is a consummate gambler throughout the entirety of the film The Sting. Many of the tropes about modern gamblers stem from the character played by Robert Redford.

He is likable, charming, difficult to read, and most of all, sorely lacking in money management skills. This is apparent when he blows $15,000 on a single roulette spin. In today’s money, that would be over $300,000!

Still, as reckless as he is, his uncanny ability to climb his way back up earns him a spot on this list.

8. Danny Ocean in Ocean’s Eleven (2001)

It takes all sorts of mettle to pull off something as high stakes as a U.S. casino heist. And no one has pulled off this feat in a film like Danny Ocean.

He plays a dangerous game that most of us would never dare to try. And he does it with all the guile one would expect of a character who has been played by both Frank Sinatra and George Clooney, two of the suavest actors of all time.

7. Teddy “KGB" in Rounders (1998)

Despite a rather glaring poker tell, Teddy KGB is one of the most intimidating gamblers in poker movie history. If anything, his poker tell was a testament to his poker prowess, given the fact that he was a revered player in spite of it.

Although he was arguably the film’s biggest adversary (we’re looking at you, Worm), he still showed immense class when he respected “gamblers’ etiquette" and paid what he owed.

6. Mickey Rosa in 21 (2008)

While he was selfish and callous, there is no doubt that Mickey Rosa was a brilliant gambler. The MIT professor was so great at it that he was able to teach his methods to a slew of his pupils and form them into a team.

Together, they took on the sprawling casinos in Las Vegas and beat them for millions. There are many expert gamblers on this list, but Mickey Rosa is the only one who was so good at it that he decided to coach it professionally.

5. Raymond Babbit in Rain Man (1988)

While this movie isn’t centered on gambling, the gambling scene is one of the most memorable gambling scenes in film. So in our book, that automatically qualifies Raymond Babbit as one of the most memorable gamblers in film.

Let’s be honest, how many of us have sat across from a ruthless blackjack dealer and wished we had Raymond Babbit’s incredible eidetic memory? If I had a $1 chip for every time I wished I had that ability, I’d have $86,000 in chips like Raymond Babbit.

4. Alan Garner in The Hangover (2009)

They say sometimes all you need is a chip and a chair. This adage was never more true than in the hit film, The Hangover. When a group of friends wakes up with nothing but lint, vouchers, and a few chips in their pockets, they must come up with $80,000 to save their friend.

Armed with only a copy of “The World’s Greatest Blackjack Book" and nerves of steel, Alan and his friends head to the casino floor, where he goes on an epic run at the blackjack table, making enough money to bring their lost friend home.

3. Sam “Ace" Rothstein in Casino (1995)

Before he got himself entangled in the sordid web of mobs and casinos, Sam Rothstein was one heck of a handicapper. In fact, his bets were known to shift the odds for every bookmaker in the country.

Being able to look at a situation and accurately assess probabilities is a gift that makes legendary gamblers so great. And as evidenced in the movie, not being able to apply that gift to one’s life outside of the casino is a trait that makes gamblers human.

2. Le Chiffre in Casino Royale (2006)

While James Bond may have a fondness for gambling, Le Chiffre is completely enamored with it. His alias even translates to “The Number".

Le Chiffre is a quintessential example of someone using their immense gambling and math talents away from the felt table. Unfortunately, it was for ignoble reasons that James Bond was determined to thwart.

Fortunately for viewers, however, it makes for a very captivating tete-a-tete watching these two gamblers clash in a battle of wits.

1. Mike McDermott in Rounders (1998)

The discerning, unflappable nature of Mike McDermott acts as a perfect foil for the ice-cold, intimidating presence of Teddy KGB. But what really sets Mike apart is his unwavering dedication to the game.

Teddy KGB’s pockets were significantly lighter after his heads-up game with Mike McDermott, but he didn’t have nearly as much to lose as Mike did.

Even when he’s down on his luck and struggling to make ends meet, Mike never once wavers in his love for poker. He continues to play because he knows that the game is ultimately about making the correct decision more often than your opponents, no matter what is at stake. And he trusts himself to do that even as he metaphorically shoves his very life into the pot against a scary foe.

And that, ladies and gentlemen, is what makes Mike McDermott the ultimate movie gambler.

What do you think of our list? Did we miss anyone? Let us know what you think on our Twitter!

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