11 Best Gambling Movies of All Time

Jamie Casey

July 12th, 2021

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Many of the best gambling films follow a similar path to one another. They often depict a very specific genre on a low budget and tend not to be instant hits, but they enjoy an indelible place in the minds of anyone that enjoys the excitement of taking a gamble.

Only one on this list of gambling films has been inducted into the National Film Registry and just two took home awards at the Oscars – but perhaps a lack of recognition is key to a movie becoming a cult classic?

Whether any more of these gambling movies will be preserved by the Library of Congress remains to be seen – it’s doubtful – but in the meantime you can start crossing them off your ‘ones to watch’ list on Netflix, Prime, YouTube or wherever you get your film fix.

1. The Gambler (1974)

   

   Aptly named, The Gambler tells the story of a university professor – played by a compelling James Caan – who has an addiction to casino gambling. As the film continues, we see Caan’s character plunge into self-destruction and his mental state become increasingly precarious.

   As his borrowing becomes steadily worse and his need for thrills threatens to endanger his life, the film builds to a steady crescendo and brilliant climax.

   A classic gambler movie, this one came out in 1974 but even today it serves as a pretty severe warning against addiction – of any kind – and to always gamble responsibly. Don't bother with the 2014 re-make starring Mark Wahlberg, the original is where it's at.

2. Uncut Gems (2019)

   

   One of the best gambling movies on Netflix for sure. Adam Sandler puts in a career-best performance as Howard “Howie” Ratner, a bungling New York City jeweller who just can’t resist the risky business of high-stakes sports betting.

   Far from a typical Adam Sandler film, Uncut Gems is darker than it is comical – although it’s not without its wit – and Howie’s chaotic descent into financial turmoil and knack for associating himself will dodgy characters make for a tense viewing.

   NBA betting plays a central part of the storyline, with former Boston Celtics and Brooklyn Nets centre Kevin Garnett excelling in a support role, playing a fictionalised version of himself (the film is set in 2012, when Garnett was a star player for the Celtics).

   The intensity may be exhaustive for non-gamblers, but those of us who enjoy the thrill of sports betting will be able to sympathise with Sandler’s character, however much of a degenerate gambler he may be. This movie provides another stark reminder that you should never gamble more than you can afford to lose.

3. High Roller: The Stu Ungar Story (2003)

   

   Released just a few months before Chris Moneymaker won the 2003 World Series of Poker main event, this movie – titled ‘Stuey’ and ‘High Roller’ in some countries – came out a little too soon to cash-in on the poker boom of the mid-2000s.

   Despite a low budget and written and directed by A.W. Vidmer, who has no other film credits on his resume, this is a well-crafted biographical movie portraying, in its entirety, the life Stu Ungar, the only three-time Wold Series of Poker winner.

   No high-octane thriller, the film chronicles the descent of an intelligent young man with great promise, who becomes addicted to drugs and gambling funds those habits by his phenomenal poker playing skills. As devastating as it is entertaining, for many High Roller: The Stu Ungar Story will be something of an undiscovered gem.

4. Molly’s Game (2017)

   

   Renowned screenplay writer Aaron Sorkin, best known for A Few Good Men, The West Wing and Moneyball, made a fine debut as a director with Molly’s Game. Based on her memoirs, this fast-paced 2017 release relays the true story of Molly Bloom’s exclusive underground poker club for wealthy high rollers.

   What makes this movie stand out from the others on the list is the lead character being a female in the male-dominated gambling business, but Jessica Chastain's portrayal of Bloom is as masterful as they come. Idris Elba also excels in the support role, while cameo appearances from Chris O'Dowd and Joe Keery (Stranger Things) add a welcome touch of humour.

   The film will leave you wondering which celebrity poker players actually took part in the games Bloom hosted in LA and New York in the late 2000s, and this article by The Ringer goes someway to establishing who the ‘Poker Princess’ had in her phonebook.

5. Rounders (1998)

   

   If The Stu Ungar Story hit the big screen a few years too early, Rounders is simply ahead of its time. Featuring a baby-faced Matt Damon and youthful Edward Norton, this 1998 release is the tale of a law student burning the candle at both ends by playing poker at night to fund his tuition fees.

   Rounders was filmed long before online poker had become a global phenomenon and so the backdrop to this film is seedy New York clubs with a single visit to the Taj Mahal’s card room in Atlantic City.

   A dark movie with a stellar cast – relatively low budget despite John Malkovich and Martin Landau having large roles – the script has you cheering for Damon’s ‘good guy’ character from the outset. You will not need to be a poker player to appreciate the storyline, but if you are you will enjoy the authenticity of the poker scenes.

6. The Cincinnati Kid (1965)

   

   The Cincinnati Kid chronicles a tense, exciting and dramatic marathon game of poker between a rising young star and a cagey old pro. Steve McQueen is the cool, detached hot shot and his adversary, Lancey Howard, played by Edward G. Robinson, displays nerves of steel, razor sharp instincts and a veteran's poise as the two players probe each other, searching for openings and seeking any advantage, however subtle.

   Both performances are excellent and have good support from a solid cast of veteran actors. The opening scene is riveting, and while the female actresses are a bit too glamorous to be believed and the poker hands are statistically nearly impossible to appear in the same game, the ending of The Cincinnati Kid is unusual and unpredictable which helps cement this poker film as an all-time classic.

7. 21 (2008)

   

   Set in the era when shuffle machines were still a thing of fiction, 21 is the fact-based story about six MIT students who were trained to become experts in card counting and subsequently took Las Vegas casinos for millions.

   The storyline features Kevin Spacey, playing maths professor Micky Rosa, educating a flock of young disciples how to play an optimum and winning Blackjack strategy. Adrenaline-fuelled trickery, betrayal and hedonism follows, meaning the cornerstones of Bringing Down The House, the book the film was based on, are intact but there is plenty of snappy, hip, fast-paced entertaining scenes to colour this big budget production.

   Oh, and a word of warning, if you are not familiar with the phrase “winner winner, chicken dinner” you might find yourself saying it a lot after watching this two-hour flick.

8. Rain Man (1988)

   

   Not a gambling film by design but a ‘road movie’ with a big segment set in Las Vegas, Rain Man earned four Oscars (including Best Picture, Actor and Director) and has become the benchmark for movies depicting characters with autism.

   When you consider the best horse racing films ever made, there would be no Seabiscuit without Phar Lap. Similarly, if there was not a Rain Man, there would probably be no Forrest Gump. It really was a landmark release in film history.

   This Tom Cruise and Dustin Hoffman collaboration is another to show blackjack can be beaten and it signposts the dim view Vegas casinos have traditionally taken on card counters. Every casino scene in the movie is realistic and it is fascinating to see both Vegas and its casinos as they were over three decades ago.

9. The Hustler (1961)

   

   This one has been selected for preservation by the National Film Registry, meaning it is considered culturally, historically, or aesthetically significant.

   A classic any way you view it, The Hustler depicts a small-time pool hustler who travels cross-country with his partner and earns good money via gambling. But his self-destructive attitude and big mouth force him to challenge legendary player ‘Minnesota Fats’.

   Shot and released in an age when online gambling was not even close to being a concept, this is no laugh-a-minute rib-tickler. Instead, The Hustler is a cynical and incredibly cold movie from start to finish.

   There's not an ounce of humour in it, none whatsoever, yet it’s still one of the best sports gambling movies ever made. That said, do not expect a film full of games of pool with trick shots galore either. But if you are a first-timer viewer of this black and white masterpiece, it will have you gripped. It was the movie which turned Paul Newman into a superstar and it is easy to understand why.

10. The Sting (1973)

    

    Three years The Hustler’s junior, The Sting stars Paul Newman and Robert Redford as a pair of old-time scammers who team up to pull off the ultimate con. It is a follow-up to their earlier collaboration Butch Cassidy and the Sundance Kid.

    This time the fix is in, the odds are set, and the boys are ready to play for the big time, both on the screen and behind the camera in this breezy, endlessly entertaining movie classic – set in the mid 1930s – which took the Best Picture Oscar in 1973.

    So full of twists and turns at every unexpected moment, The Sting – which features plenty of poker and a phony off-track betting operation – never stops drawing you into all of its traps. All of it is performed at a fast clip and the performances have all the nuances needed to keep you entertained and in suspense.

11. Casino (1995)

    

    In 1995, for a fifth time, Robert De Niro and Joe Pesci teamed up to make Casino. It had been five years since the pair had taken the world by storm with the acclaimed gangster epic Goodfellas, which was directed – like Casino – by Martin Scorsese.

    Casino is a lesser acclaimed gangster epic with similar themes, narrative, style and casting but, set entirely in Las Vegas, it is possibly the most famous of all gambling movies. Positively gruesome in some places, it's not one for the faint-hearted.

    There are no tense poker hands, no pool hustling, no odds-fixing nor true love story, yet it’s widely considered one of the best Vegas movies.

    The film is a factual tale of greed, deception, money, power and murder. But such is this action-packed depiction of Vegas during the final years of its gangster control, you easily forget gambling is not the theme of the film, it is only the common denominator which brings all the elements together.

    Delve deeper into the brilliance of this Scorsese masterpiece with our full nod to the greatest gambling film of all time.