The most legendary fictional gamblers of all time

The most legendary fictional gamblers of all time

Photo: Raka Miftah via Pexels

Gambling has risen in prominence in the cinematic world and has become increasingly glamourised on the big screen. There is an innate sense of excitement about watching the villain of the piece fall apart at the poker table or the lead role holding their nerve to claim the big prize.

We’ve become compelled to watch films that have a strong element of gambling or casino playing running through them. The relationship between gambling and film is deep-rooted. Ultimately, we will see more movies in the future that will tackle the subject of gambling. But what makes a great fictional gambling character?

In this article, we will run through eight of the most legendary fictional gamblers of all time and explain why they deserve such credit. While this is done in no particular order, we will explain how iconic the characters on the following list are regardless of their skills.

Jim Bennett in The Gambler (2014)

This film stars Mark Wahlberg, who plays Jim Bennett, a professor of literature whose life philosophy leads him into the world of gambling.

Unfortunately for Bennett, his casino skills are drawn into question and he ends up owing the wrong people a lot of money – and he has to pay it back within a week or else he will face the consequences. He enlists the help of students to dig him out of trouble, but things just get steadily worse for him. 

While the film’s title suggests otherwise, Bennett is keen to remind us that he’s not a heavy gambler. Wahlberg gave a dynamite display in this film, and those who are after a typical Wahlberg thriller won’t be disappointed.

Le Chiffre in Casino Royale (2006)

A suave James Bond usually takes on the pivotal role at the casino table claiming big wins while sipping on a Martini that is shaken but not stirred! However, the shoe is very much on the other foot in Casino Royale.

Indeed, Le Chiffre is something of a poker specialist. Le Chiffre, who is played by Mads Mikkelsen, invests significant sums in an effort to short an airline company’s stock.

007 is played by Daniel Craig and he tries his all to stop Le Chiffre getting his own way. While Craig comes across as an amateur card player, this film is packed with action and is a thrill from start to finish.

Photo: Gaumont Columbia Tristar Films

Alan Garner in The Hangover (2009)

“What happens in Vegas, stays in Vegas,” the saying goes! There is something intrinsically funny about the dialogue and the hilarity of the hapless characters in The Hangover – none more so than Alan Garner, who is played by Zach Galifianakis.

The movie is centred on three friends fighting a hangover, trying to recover their memories of the night before. In one part of the plot, they try to find $80,000 to pay back a gangster. They end up heading to the blackjack table in Las Vegas, and Garner proves to be very adept at the game, which helps his friends pay off their debts.

Dan Mahowny in Owning Mahowny (2003)

This gambling film is based on the events of a true story, and it revolves around a Canadian bank employee who embezzles over $10m to feed his gambling addiction.

Dan Mahowny, who is played by Philip Seymour Hoffman, the goes on to steal increasingly larger amounts, which makes some people within the company suspicious.

Mahowny is rather single-minded in his attitude towards risk, and he is singled out as being a high roller. Gambling is what makes Mahowny tick, and the film perfectly captures his successes and his depressing failures. It is a fabulous film and will leave you on the edge of your seat!

Bret Maverick in Maverick (1994)

With Western films, there is a common stereotype that involves gunfights and cowboys playing card games in saloons and accusations of cheating flying about.

In Maverick, our man is Bret Maverick, who is played by Mel Gibson. In this film, Gibson is a card-playing conman who uses every possible trick in the book so that he can enter a high-stakes poker tournament.

While this film deviates from the normal Western, it is good solid fun and perfectly captures the adrenaline that arises from gambling.

Raymond ‘Rain Man’ Babbitt in Rain Man (1988)

Based on the relationship between two estranged brothers played by Tom Cruise and Dustin Hoffman, the main focus of this film isn’t gambling.

The term ‘Rain Man’, which is used in modern lexicon, describes someone who has remarkable powers of recall. Hoffman is able to count cards in this film like nobody else, and his skills see him quickly compile big stacks of chips and the unwanted attention of casino staff.

Hoffman and Cruise gave accomplished performances, and you can learn a lot from the film. Perhaps the movie’s longevity and relevance to gambling are its enduring qualities.

Photo: DR

Danny Ocean in Ocean’s Eleven (2001)

Perhaps this is one of the most underrated films celebrated on this list, but George Clooney leaves us in no doubt that he’s a mastermind in Ocean’s Eleven.

Often, characters in gambling films provide sobering cautionary tales of what happens when things go awry. From the early scene in the film where Clooney and Brad Pitt square off at the poker table, Ocean’s Eleven exudes a good deal of charm.

The filmmaker isn’t necessarily interested in the intricacies of gambling, but Ocean’s Eleven is very entertaining and re-watchable.

Teddy KGB in Rounders (1998)

This movie is essentially the gambling equivalent of Citizen Kane. In this film, a ‘rounder’ is known as someone who travels from place to place and is looking to play high-stakes cash games.

While Matt Damon is cast in the lead role, it is the Russian poker shark Teddy KGB, played by John Malkovich, who takes the credit for the most memorable gambler. Malkovich produces an excellent performance and is very entertaining to watch.

Damon doesn’t quite cut the mustard for some, but Malkovich, who comes across as a mobster, is the real star attraction and gives the film some much-needed pizzazz. 


There have been so many gambling-related films over the years, but we are happy with the characters that we have chosen to feature in this list. There were several additional contenders on our shortlist, but when pitched against those above, they didn’t quite make the cut.

What is apparent in all of the characters is a single-mindedness in their dogged pursuit of winning big, and they didn’t care who they hurt or trampled over in order to get their way.

If we were forced to pick our favourite fictional gambling character, then we would lean towards Raymond Babbitt in Rain Man. There are so many enduring features about this film and it would still resonate with a modern audience.

If you’re feeling inspired by these legendary gamblers, why don’t you head over to check out how games such as poker and blackjack work? Once you get an understanding of how bonus offers and game selection work, there’s nothing to stop you signing up to your favourite casino and start playing for real money.

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