11 Best Gambling Movies of All Time

Jamie Casey

March 28th, 2019

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There are many classic gambling movies: too many, in fact, to list. However, we at Gambling.com have trawled through the film archives and picked out what we think are the "11 Best Gambling Movies of All Time." There were many that did not make the list and, of course, you will agree and disagree with some of the choices. However, the following films cover a pretty broad range of ‘gambling-related topics’– everything from casino gambling to online gambling to hustling and more. Most important of all is that they are simply, good movies.

1. High Roller: The Stu Ungar Story

   

   One of the better biographical gambling movies around, the affectionately-named Stuey features Michael Imperioli playing Stu Ungar, a high roller famed for being the only poker player to ever win three WSOP Main Event tournaments. A.W Vidmer’s spectacle is no high-octane thriller but shows the breakdown of a man who once had everything. The film portrays the gambler’s whole life, from beginning to end, showing the hedonistic highs and terrible lows. Eventually losing most of his money on horses, the story of Stu’s meteoric rise to the top of the gambling world and then dramatic fall is as devastating as it is entertaining.

2. The Cooler

   

   William H. Macy plays an unusual character in Wayne Kramer’s movie. Macy is the ‘cooler’ of the title – a man whose luck is so bad that casinos employ him to stand at the table of punters on hot streaks. Without fail, their luck changes and the casino’s house edge is restored. However, when the cooler’s own fortunes change he suddenly finds himself being the lucky charm of every gambler in Vegas – much to the chagrin of the casinos that employ him. A fun premise that’s backed up by a superb central performance, this is a great insight into casino gambling superstitions and the concept of luck.

3. Seabiscuit

   

   Though not focused on online gambling or casino gambling, Seabiscuit tells the charming story of a jockey’s, a trainer’s and a horse’s rise from rags to riches. Jeff Bridges plays a depressed individual down on his luck but with one possible redeeming feature in his life; Seabiscuit, an apparently useless horse found by a cowboy trainer (Chris Cooper). Tobey Maguire plays the unlikely jockey who goes on to steer Seabiscuit to numerous victories in one of the great underdog stories of the twentieth century. This is about as stirring a true story as you’ll find anywhere.

4. Rounders

   

   Featuring a youthful Matt Damon, Rounders is the tale of an entrepreneur who pays for his university fees by winning at the poker table. The film is full of famous faces, with John Malkovich and Edward Norton also making appearances. The movie’s showdown culminates in a dazzling high stakes game, with Malkovich playing the irrepressible poker baron that Damon must try and defeat. The film is carried along by brilliant performances – Norton, in particular, is spectacular – and authentic depictions of poker strategy and table banter that few other gambling movies render so successfully.

5. The Gambler

   

   Aptly named, The Gambler tells the story of a university professor (played by a compelling James Caan), who has an addiction for 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. This is one for the gambling purists, who will be able to identify regularly with the character on screen. It also serves as a pretty severe warning against addiction – of any kind.

6. The Cincinnati Kid

   

   Another film with a host of good performances, The Cincinnati Kid, starring Steve McQueen, tells the story of an up-and-coming gambler who pits his wits against the high roller of the day, Lancey Howard. Played with verve by Edward G. Howard, Lancey agrees to take on McQueen, seeing as the Kid had made his name only in backroom games with little serious competition. The Kid is further hampered by a series of distractions – not least a beautiful girl – which threaten to topple his chances. The film culminates with both players raising their stakes and, in an exciting finale, one of them thrillingly coming out on top.

7. 21

   

   Based on a remarkable true story, 21 is a modern classic of the casino gambling movies genre. Set in the era before online gambling had set down its stall, this is the tale of a maths professor (Kevin Spacey) training up a group of talented students to count cards in the major casinos on the Vegas strip. What follows is a thrilling tale of adrenaline-fuelled trickery, betrayal and hedonism that wouldn’t be believable if it hadn’t actually happened. Anyone out there with even a passing interest in casino gambling, blackjack and card counting will enjoy this exciting ride.

8. The Hustler

   

   A classic any way you look at it, The Hustler is a tale set in an era when online gambling was about as close in reality to mankind living on Mars. Paul Newman’s “Fast” Eddie Felson is the upstart with an attitude trying to pit his pool skills against the legend that was Minnesota Fats. A chastening experience soon sees him out of pocket and down on his luck, and only the ruthless mentoring of manager Bert Gordon can take him anywhere near where he once was. This is one of those gambling movies with its heart right in the origins of the pool-halls and backrooms that US gambling was built on.

9. The Sting

   

   The star duo of Paul Newman and Robert Redford – who combined so successfully over the course of their careers – play two con men, one a beginner and the other a professional. Together they target a high-flying criminal boss who loves a good gamble and who is after Redford’s character from the outset for a previous swindle. Gambling movies rarely have as many twists and turns as you’ll find here, as the ‘long con’ gets ever more complicated and the danger levels for both protagonists reaches a crescendo. Finally, a dramatic denouement provides an ample payoff for a truly nail-biting, suspense-filled thriller.

10. Casino Royale

    

    There are two versions of Ian Fleming’s story, but without doubt the most accomplished is director Martin Campbell’s take, starring Daniel Craig. Set at breakneck speed, the story follows James Bond as he takes on another villainous figure, this time in the form of the poker-playing, torture-inflicting Le Chiffre. The most memorable scene in the movie – and one of the most unforgettable scenes in recent film history – centres on an incredible showdown at the felt in Monte Carlo when Bond takes on his adversary in an all-or-nothing game. The pace is furious, Eva Green is sumptuous and the poker – simply jaw-dropping.

11. Casino

    

    Perhaps the most famous of all gambling movies and a sweeping classic that’s on most film buffs’ Top Ten All Time Favourites lists, Casino is the epic tale of mob-controlled casino gambling in Vegas. Robert De Niro and Joe Pesci star, the first as a casino owner with mafia ties and the latter as a psychotic enforcer whose increasingly erratic behaviour starts to threaten both their lives. Throw into the mix the seductive charms of Sharon Stone, some towering support performances and some of the most harrowing and memorable scenes in film history, and you have the perfect combination for a classic great.