The Greatest Gamblers from Fiction

by Tim | May 05, 2022

The Greatest Gamblers from Fiction

The cinematic world is filled with incredible gambling features that often glamourise the experience for the big screen. In these movies, we get a glimpse of the good, the bad, and the downright ugly parts of the gambling industry.

If you’ve ever taken a break from the best online slots to try your hand at the poker table or slot machines at a brick and mortar establishment, then you’ll know that there really are some interesting characters out there.

Hollywood has produced some compelling and convincing roles in its films. Whether you only play online casino games like mobile slots or you hit the floor at your local casino regularly, you’re bound to have watched many of them.

Let’s take a look at some of the legendary fictional characters that loved to gamble.

Alex Freed: The Gambler (1974)

Axel Freed is a seemingly normal professor played by James Caan in The Gambler. However, his students, parents and girlfriend don’t realise that he just happens to be addicted to gambling. He eventually gets into serious debt, and first, his girlfriend lends him money, then his mother, and finally, it all comes crashing down when the bad guys come looking for their payments. Caan plays the role perfectly, and he leaves viewers uncomfortable, unsettled, and in disbelief that through all his troubles, he keeps on gambling. This is an honest and epic gambling movie depicting a realistic character who shows how everything can go wrong when people aren’t responsible with their gambling activities.

Charlie Waters: California Split (1974)

 A man dropping cards between his hands on a dark background.

This is another excellent gambling movie that was released in the same year as The Gambler, but where The Gambler was often uncomfortable, California Split is humorous while dealing with the shady underbelly of the gambling world.

Elliott Gould plays Charlie Walters, a gambler who teeters on the edge of committing serious crimes; however, Gould’s performance is carried off with such humour and aplomb that he will have you eating out of his hand by the end of the film, rather than condemning his often questionable decisions.

Bret Maverick: Maverick (1994)

Now, this certainly isn’t a film based completely on gambling. It is actually a rowdy Western with the usual gunfights and cowboys, along with a slight twist. The main character, Bret Maverick, played by Mel Gibson, is a card-playing conman. He tricks his way into playing high-stakes poker tournaments where he wins huge stacks of cash and gets into the usual trouble that you’d expect in gun-toting saloons in the West.

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

Dustin Hoffman plays Raymond Babbitt in this movie about the relationship between two estranged brothers. Raymond has the uncanny ability to recall remarkable things, and his brother, played by Tom Cruise, uses his skills to count cards, compile big stacks of chips, and eventually attract unwanted attention from the staff at the casino.

It’s the performances from both Hoffman and Cruise that took this movie to great heights, and their troubled relationship is at the heart of this excellent film that all gamblers should take the time to watch.

Teddy KGB: Rounders (1998)

A “rounder” is someone who travels from place to place and state to state, looking for high-stakes cash games to take part in. While Matt Damon plays the lead role in this movie, it’s actually the Russian poker shark, Teddy KGB, played by John Malkovich, who steals the show.

Malkovich offers an excellent performance that is highly entertaining to watch, and his mobster character took the film to its lofty levels.

Danny Ocean: Ocean’s 11 (2001)

The word “robbery” spelt out with Scrabble pieces on $100 bills.

Ocean’s 11 is less a tale of caution than an adrenaline-fueled casino heist gone wrong. Danny Ocean is the mastermind of a group of accomplices looking to pull off three simultaneous heists on Las Vegas’s biggest casinos.

Played by George Clooney, Danny Ocean is brash, charming and offers plenty of humour to the film. Clooney is the perfect man of action for this high-octane film that is supremely entertaining and rewatchable.

Dan Mahowny: Owning Mahowny (2003)

Philip Seymour Hoffman was the actor behind Dan Mahowny in the 2003 film Owning Mahowny. Mahowny is a Canadian bank employee who manages to embezzle $10 million from the bank for his gambling addiction. These increasingly large transactions start to make people within the company highly suspicious.

However, Mahowny has a single-track mind that leads only to gambling. His character is simultaneously incredibly likeable while being rather off-putting too, and Seymour Hoffman perfectly portrays the highs of Mahowny’s successes and the depression that comes with his failures.

Alan Garner: The Hangover (2009)

The Hangover was one of the funniest movies to come out of Hollywood in the early 2000s, and the character of Alan Garner was one of the biggest drawcards. Played by Zach Galifianakis, Garner is the cause of most of the trouble that the cast of The Hangover find themselves in, and his hapless character is as hilarious as it is frustrating.

After drugging his friends, they manage to lose $80,000 dollars, which they now need to find to pay back a gangster. Luckily, Garner comes to the rescue with his adept play at the blackjack table, and despite being the reason they are in the mess in the first place, he manages to help his friends out so they can pay off their debts.

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