10 of the Best Gambling Related Movies

GAMBLING goes hand in hand with drama, with agony or ecstasy riding on one flip of a card, one swing of the boot or a photo finish.

So it’s no surprise to see it at the heart of many a movie. with Hollywood’s finest bringing betting to vivid life on the big screen.

Debates will rage forever about the finest gambling film but here’s my top 10, in no particular order. 

THE HUSTLER (1961)

This Paul Newman classic ticks all the boxes for an essential gambling movie. Although it’s mostly about pool hustling, the film also features poker and a trip to the Kentucky Derby. Fast Eddie Felson, the hustler played by Newman, is obsessed about beating a legendary pool player called Minnesota Fats. He travels across the country to challenge Fats, played superbly by Jackie Gleason, but fails to quit while he’s ahead and ends up losing all the money he has won.

With the help of Bert Gordon, a professional gambler who offers to stake Eddie in return for 75 per cent of his winnings, he eventually gets a second crack at Fats. However, Eddie finds out there are more important things than hustling after his love interest, an alcoholic called Sarah Packard, takes her own life on the eve of the game.

The film won two Academy Awards and sparked an upsurge of interest in pool, a game which had been in chronic decline.

ROUNDERS (1998)

Branded “the best poker movie ever made” by professional Vanessa Rousso, this is the film that helped me fall in love with Texas Hold Em. Having lost $30,000 on a single hand, Mike McDermott (Matt Damon) turns his back on poker and vows to concentrate on his law studies.

But he’s dragged back into the seedy world of underground games when his friend Worm (Edward Norton) gets out of prison and starts hustling again. Worm’s underhand tactics and mounting debts dig them both into a deeper hole, until Mike is left with no option but to enter another high-stakes game with the Russian mobster (an over-the-top John Malkovich) who took the 30 grand from him. 

THE STING (1973)

Set in the 1930s, this classic film with Paul Newman and Robert Redford was based on the real-life capers of con men Fred and Charley Gondorff. The Sting tells the story of grifters Johnny Hooker (Redford) and Henry Gondroff (Newman) as they attempt to pull off the dangerous stunt of conning mob boss Doyle Lonnegan (Robert Shaw).

Full of twists and turns, poker and horse racing play key roles in the complicated plot as the duo use cunning tricks to take Lonnegan to the cleaners. The film, directed by George Roy Hill, won seven Oscars and is widely considered one of the greatest movies ever made.

MISSISSIPPI GRIND (2015)

A modern classic, this movie follows the exploits of gamblers Curtis (Ryan Reynolds) and Gerry (Ben Mendelsohn) as they embark on a spree down the Mississippi river. There’s nothing the boys won’t have a punt on and Mississippi Grand is arguably the ultimate gambling movie as it features poker, pool, greyhound racing, horse racing, roulette, black jack, craps and even basketball. A fascinating examination of addiction, it shows the depths some gamblers will sink to in a bid to stay in the game. 

THE CINCINNATI KID (1965)

Released just four years after The Hustler, this tells a similar tale, with poker replacing pool. Eric Stoner, who goes by the nickname The Kid, is desperate to take down Lancey Howard, a poker player so feared he is known as The Man.

The Kid (Steve McQueen) eventually gets his desired showdown with The Man (Edward G Robinson) but is dismayed when he finds out his friend Shooter (Karl Malden) has been cheating in his favour in his role as dealer. Another dealer takes over and the duel comes to down to one final hand, with everything riding on the last turn of the card. 

13 TZAMETI (2005)

Tells the story of Sebastien, a Georgian immigrant in France who becomes embroiled in a deadly underground gambling event. He steals an envelope belonging to his deceased employer, which directs him towards a job in a secluded house in the forest. But the job turns out to be a series of Russian roulette games, with mobsters waging huge bets on which players will die and survive.

The tension-packed film won an award at the Sundance Festival and was subjected to an awful American remake in 2010 involving Jason Statham and 50 Cent that had many viewers thinking about pointing a gun at their own heads.

CASINO ROYALE (2006)

Originally released in 1967 with David Niven as James Bond, the Daniel Craig reboot for the new millennium is a far better movie. While Niven’s Bond plays Baccarat against his nemesis Le Chiffre, Craig wages war in a high-stakes Texas Hold Em poker tournament.

The stakes grow higher and higher as the tournament continues until it all boils down to a final $115 million hand. The first Bond film with Craig in the lead role, Casino Royale helped reinvent the franchise, earning critical praise for giving the super spy a darker edge. 

CALIFORNIA SPLIT (1974)

Acclaimed director Robert Altman brought to vivid life this screenplay from actor Joseph Walsh, who wanted to write about his own battle with gambling addiction. California Split sees two gamblers strike up a friendship after they are wrongly accused of colluding during a poker game. At the start of the film Bill Denny (George Segal) is just a casual gambler but he becomes more and more obsessed after coming under the wing of Charlie Waters (Elliott Gould).

Bill soon racks up huge debts but tries to dig himself out of trouble by pooling his cash with Charlie to enter a high-stakes poker game. The duo then embark on a memorable night at the casino before finally going their separate ways.

HARD EIGHT (1996)

The debut feature of director Paul Thomas Anderson, this gripping drama examines the complex relationship between aging gambler Sydney (Phillip Baker Hall) and his protégé John (John C Reilly). Sydney teaches John the tricks of the trade in Vegas and helps turn him into an accomplished gambler.

John eventually falls for a cocktail waitress in Reno called Clementine (Gwyneth Paltrow) who also works as a call girl. But he needs Sydney’s help after they kidnap one of Clementine’s punters for refusing to pay up and his mentor’s dark past as a mobster then threatens to ruin their own relationship.

RAIN MAN (1988)

Casino blackjack plays a key role in this comedy-drama about estranged brothers who are reunited in the wake of their father’s death.

The obnoxious Charlie Babbitt (Tom Cruise), expects to inherit all the cash, only to be left with just a car as the rest of the money has gone to a brother he never knew about, an autistic savant called Raymond (Dustin Hoffman). The brothers eventually embark on a road trip together as Charlie finds himself falling deeper and deeper into debt.

But his problems are solved when he puts Raymond’s card counting skills to use at a casino in Vegas, fleecing them for over $86,000 before they are eventually kicked out. The film won four Academy Awards, including best picture and best actor (Hoffman). 

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