The 30 Best Gambling Movies of All Time

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These films are all about high stakes and the tumultuous consequences that come with them

The drama surrounding the world of gambling can suck you in with its tales of big wins, devastating losses and criminal masterminds.

From a cinematic standpoint, we’ve been treated to a host of films that delve into the inner workings of casinos, bookies, and pool sharks. There’s a lot of entertainment to be had when a movie is all about placing bets on horse races, boxing matches, and assorted sports games. And it’s easy to get caught up in the plight of the individuals who find themselves in the crosshairs of the bigwigs that run their own gambling underworld.

Robert De Niro, Adam Sandler, George Clooney, Tom Cruise and a host of other world-class actors have appeared in some of the greatest gambling movies ever put on the big screen. Thankfully, this list goes through the trouble of finding 30 of them and are required viewing for movie buffs everywhere.

30. ‘21’

While 21 isn’t exactly a critical darling, it still pulled in a ton of curious viewers and nabbed the number one spot during its box office debut. The fact that this film’s synopsis is lifted from true events makes it all the more intriguing. Six genius MIT students are trained in the art of card counting and go on to ransack Las Vegas casinos in the most efficient way possible. Their intellect pays off as they rack up millions of dollars in winnings, but their actions bring the wrong type of attention to their gambling schemes. 21 can been seen on Vudu, Amazon Prime Video, YouTube, Google Play Movies & TV, iTunes and Netflix.

29. ‘Bookies’

When a pair of college students who’re sick and tired of losing big on sports bets kick off a bookmaking operation of their own, their fortunes quickly change. But with this quick success comes prying eyes and a whole lot of suspicions from the local authorities, rival bookies and loved ones. Bookies is all about a bunch of young go-getters who hit it big and make a power play that could make them the most powerful bookies in town. You’ll get wrapped up in the manner in which these four young bookies pull off their biggest bet and how they choose to ride off into the sunset. Bookies can be watched via Tubi and Amazon Prime Video.

28. ‘High Roller: The Stu Ungar Story’

Here’s another gambling film that’s based on a true story. And this time, its main focus centers on a gambling superstar that becomes synonymous with the poker scene. High Roller: The Stu Ungar Story follows Stu as he goes from a young gambling prodigy to a legendary pro who ends up claiming the top spot at the Main Event portion of the World Series of Poker. This selection is a fascinating biopic that provides viewers with a deeper look into the world of gambling and how high levels of success can eventually make way for crushing lows.

High Roller: The Stu Ungar Story can be seen on YouTube, iTunes, Google Play Movies & TV, Vudu and Amazon Prime Video.

27. ‘The Cooler’

Bernie Lootz is very efficient at what he does – he works at a Las Vegas casino as a sort of “bad luck bringer” that goes out of his way to jinx gamblers into losing. Shelly Kaplow, the casino’s boss lady, appreciates him and his ability to keep her casino on the winning end of things. But Bernie’s “cooler” abilities start to falter when he comes across a waitress named Natalie Belisario, who he falls head over heels for. Once Shelly takes notice of Bernie’s changed behavior, the plotline within The Cooler blossoms into something you’ll become heavily invested in as it unfolds. 

You can catch this film on YouTube, iTunes, Google Play Movies & TV, Vudu, Amazon Prime Video and Hulu.

26. ‘Rounders’

Matt Damon stars in this movie all about placing big bets and fighting to escape crippling debt. Matt’s character (Mike McDermott) ends up losing a ton of money during a poker game against a Russian gangster. After experiencing such a devastating loss, Mike leaves the poker scene behind due to his girlfriend’s pleas to leave the game behind. But the game comes calling once more when Mike finds out his friend Lester “Worm” Murphy needs to pay off a huge debt to the same Russian mobster that Mike took a major loss to. Rounders follows Mike and Lester as they try to work the system to their advantage and find a way to get one over on the man who’s responsible for their financial misfortunes. 

You can watch this film on YouTube, iTunes, Google Play Movies & TV, Amazon Prime Video and Netflix.

25. ‘The Last Casino’

The Last Casino is kind of like a Canadian take on 21. A down on his luck college professor hatches a get rich quick scheme with the aid of three students of his choosing. After being banned from the casinos within Ontario and Quebec, the professor relies on his card-counting experts to take his place at those casinos and gamble their way to big money. The drama surrounding the professor’s debts and the ways in which his young protégés attempt to wipe them way makes this film a supremely absorbing experience.

The Last Casino can actually be seen on Vimeo.

24. ‘The Gambler’ (1974)

One’s addiction to gambling can be immensely severe. An English professor by the name of Axel Freed knows this sentiment all too well. The Gambler (1974) follows Axel as his life spirals out of control due to his out of control gambling habits. Things reach a fever pitch once he recklessly gambles away a huge sum of his casino earnings, which proceeds to put his life in danger.

The Gambler (1974) can be seen on YouTube, Google Play Movies & TV, Vudu, Amazon Prime Video and iTunes.

23. ‘The Cincinnati Kid’

Poker extraordinaire Eric Stoner has made it his mission to become the best poker player in town. Known around the local poker scene as “The Cincinnati Kid,” Eric decides to challenge someone even better than him – a fellow poker master by the name of Lancey “The Man” Howard. After getting set up with Howard for a winner takes all poker games, Eric discovers that the odds are being fixed in his favor. This revelation pushes Eric to defy such a dishonorable victory and show everyone that he can win the match through his skills alone. The Cincinnati Kid shows that there’s an honor to be had, even in the high-stakes world of big-money poker games. 

This film can be viewed on YouTube, iTunes, Google Play Movies & TV, Vudu, and Amazon Prime Video.

22. ‘A Big Hand for the Little Lady’

On an annual basis, the town of Laredo, Texas becomes the epicenter for the most important poker game in the state. Five of the wealthiest men in the area come together to risk it all while an interested crowd watches them with bated breath. An ex-gambler ends up wandering into town in the midst of the big poker game and finds himself going right back to his former addiction. When things become too tough to bear for the latest addition to the game, the ex-gambler’s wife steps in to take his place and defy the odds as she takes on her wealthier opposition.

A Big Hand for the Little Lady can be seen on YouTube, iTunes, Google Play Movies & TV, Vudu and Amazon Prime Video.

21. ‘Lock, Stock and Two Smoking Barrels’

If you’re looking for a gambling film that has a lighter edge to it, then this pick should elicit a few laughs. Lock, Stock, and Two Smoking Barrels is a British crime/comedy that stars Jason Statham and Vinnie Jones. The plot revolves around four friends who decide to put all their cash together and enter a major poker game against a big-time crime boss. That crime boss takes the win under dubious means, which forces the main man who convinced his crew to enter the game to pay up or be forced to give up his father’s pub as collateral. In order to pay that debt, the four friends get in way over their heads when it comes to acquiring those funds through illegal means. And that’s when plenty of hilarity ensues. 

Lock, Stock and Two Smoking Barrels can be viewed on YouTube, iTunes, Google Play Movies & TV, Vudu and Amazon Prime Video.

20. ‘Hard Eight’

Hard Eight features three A-list actors that you might not have expected to see in a film such as this one – John C. Reilly, Gwyneth Paltrow and Samuel Jackson. When a professional gambler by the name of Sydney runs into a fellow gambler named John, Sydney takes John under his wing and teaches him how to truly be successful in the world of gambling. This process seems to go well at first, but things take a turn for the worst when both men come into contact with a local prostitute and a sketchy casino patron.

Hard Eight can be seen on Crackle, YouTube, Google Play Movies & TV, Vudu and Amazon Prime Video.

19. ‘Owning Mahowny’

Philip Seymour Hoffman plays the part of a bank employee named Dan Mahowny that lives a double life. He comes off as a hard-working man and a loving boyfriend to his closest associates. But in reality, he’s actually addicted to gambling and feeds his addiction by stealing money from various bank accounts in order to fulfill the debts owed to his main bookie. Eventually, Dan’s gambling troubles start to become much too hard to hide. Dan’s bank account thievery and gambling debts then threaten to cost him the other life he fought so hard to keep intact.

Owning Mahowny can only be seen through physical means on DVD.

18. ‘Mississippi Grind’

Mississippi Grind plays out like a gambling road trip tale that takes viewers on a wild ride through the South. When Gerry ends up meeting a gentleman by the name of Curtis (played by Ryan Reynolds), Gerry deems him his new lucky charm. So much so that Gerry takes Curtis on the road with him as he taps into his good luck during their gambling tour around the South. Gerry hopes that with Curtis by his side, he’ll be able to hit it big at a high-stakes poker game in New Orleans. Mississippi Grind is the perfect road trip film that just so happens to be tied to big money bets and a nail-biting poker game.

You can check out this film on Amazon Prime Video, YouTube, Google Play Movies & TV, Vudu, iTunes and Netflix.

17. ‘Bugsy’

Bugsy is not only a cinematic peek into the glitz and glamour seen within the world of gambling, but it’s also a fascinating biopic that’s all about legendary New York mobster Benjamin “Bugsy” Siegel. After moving from the big city to Hollywood, Bugsy ends up finding love and success from his underground gambling rackets. Soon after, he develops an idea around a gambling epicenter that people from all over the US could come and place their bets. That gambling haven ends up being Las Vegas, a place that’s attributed to Bugsy’s forward-thinking approach. This biopic delves into everything that made Bugsy what he was and how he helped develop Las Vegas into what it is today.

Bugsy can be viewed on Crackle, Vudu, Amazon Prime Video, YouTube, iTunes, and Google Play Movies & TV.

16. ‘Win It All’

Eddie Garrett has really done it now. After agreeing to keep an eye on a duffel bag full of money for a friend that’s heading to prison, Eddie gives in to his gambling demons and ends up using the money to indulge his addiction. Sadly, that decision ends up putting Eddie in some deep debt. His troubles quickly worsen once Eddie finds out his friend is getting out of prison sooner than expected. This forces Eddie to find a way to gamble his way into getting all his friend’s duffle bag money back in full.

Win it All is a Netflix exclusive.

15. ‘Dinner Rush’

Not only does Louis Cropa run a successful restaurant alongside his star chef son, but he also handles part-time bookmaker duties on the side. Louis’ fine dining establishment attracts a number of shady characters, including two gangsters whom one of Louis’ chefs is indebted to. Dinner Rush delves into one particularly busy evening at Louis’ restaurant when those two gangsters and a host of other eccentric personalities converge there all at once.

This film can only be seen and obtained via DVD.

14. ‘Holy Rollers: The True Story of Card Counting Christians’

This documentary covers one of the most popular and well-funded blackjack teams in the US of A. It just so happens that these gambling pros are also heavily devoted, churchgoing Christians. Holy Rollers: The True Story of Card Counting Christians offers an inside look at the rise of this blackjack juggernaut team and how they move within the gambling and religious circles they frequent.

You can catch this documentary on Tubi, Amazon Prime Video, Vudu, YouTube, iTunes and Google Play Movies & TV.

13. ‘The Color of Money’

Paul Newman and Tom Cruise star in this film that’s all about the game of pool. Newman plays the part of former pool hustler “Fast Eddie” Felson, who decides to make a comeback to the game he once dominated. However, he does so by taking on the role of a teacher as he leads a young pool player to greatness. That player is Vincent Lauria (played by Tom Cruise), who goes on to learn the in’s and out’s of proper pool playing and scamming. But when Eddie and Vincent’s partnership falls apart, they eventually end up on opposite ends and confront each other in the game they both love so much.

The Color of Money can be seen on YouTube, iTunes, Google Play Movies & TV, Amazon Prime Video, Vudu and MAX GO.

12. ‘Ocean’s Eleven’ (2001)

It’s always a rare case when the remake of a film ends up surpassing the original. The 2001 version of the 1960 Rat Pack film ends up being a far superior rendition that features a who’s who of Hollywood A-listers. George Clooney stars as Dapper Danny Ocean, a thief who’s up to no good just hours after being released from his parole. He puts his big casino heist plan into motion alongside a top-notch crew. That ragtag group of fellow thieves consists of familiar faces such as Brad Pitt, Matt Damon, Don Cheadle, Bernie Mack, etc.

Ocean’s Eleven (2001) can be viewed on YouTube, iTunes, Google Play Movies & TV, Vudu and Amazon Prime Video.

11. ‘Uncut Gems’

Adam Sandler is known for starring in some…well, questionable comedies. But his role in Uncut Gems reminded everyone that he’s a force to be reckoned with when he’s given incredible material to work with. Adam takes on the role of a lovable NYC jeweler who loves playing it big when it comes to betting. When he makes one of the biggest bets of his life, his world starts to cave in around him as debt collectors come calling. Uncut Gems follows Adam’s character as he looks to keep his life intact as his high-risk gambling endeavors threaten to tear it all apart.

Uncut Gems can be seen on Amazon Prime Video, YouTube, Vudu and Google Play Movies & TV.

10. ‘Molly’s Game’

Molly’s Game is based on the true story of Molly Bloom, a world-renowned Olympic-class skier. Molly’s athletic career is certainly noteworthy, but her side gig garnered even more interest once it was made public. Molly just so happened to be running an exclusive poker game ring for an entire decade that welcomed celebrities, business tycoons, and even mobsters. After being arrested during a massive FBI sting, Molly comes into contact with a criminal defense lawyer and relays more of her enthralling life story to the viewing audience.

Molly’s Game can be seen on YouTube, Google Play Movies & TV, Vudu, Amazon Prime Video, and Netflix.

9. ‘Casino’

Casino is high atop a list of films that are most popular amongst followers of the gambling scene. Robert De Niro, Joe Pesci, Sharon Stone, and Don Rickles are just some of the major names attached to this 90s cinematic classic. Casino follows Sam “Ace” Rothstein, a mobster who takes on the job of running a casino owned by his overseers. Things go well at first, but his reckless enforcer, con artist ex-girlfriend, and a slew of dirty politicians disrupt his casino’s operations and eventually put his life in danger. You can check out

Casino is on YouTube, iTunes, Google Play Movies & TV, Vudu, Amazon Prime Video, Hulu, Sling TV, and the Starz app.

8. ‘Rain Man’

Tom Cruise appears in his second gambling movie role as car dealer Charlie Babbitt, who doesn’t have the best relationship with his now-deceased father. After finding out that a massive sum of inheritance money is being left to an autistic brother (played by Dustin Hoffman) he never even knew he had, Charlie gets the bright idea to somehow lift all of that money from his older sibling. This scheme soon leads to Charlie taking his autistic brother on the road with him for a life-changing excursion. All the while, Charlie relies on his brother’s amazing mathematical skills to help him win big at every gaming table they come across during a stop in Las Vegas. This moment then leads to a change in character for Charlie that makes this film a real tearjerker that’s bound to hit you right in the feels.

Rain Man can be seen on Tubi, Vudu, YouTube, Google Play Movies & TV, Amazon Prime Video, iTunes and the Max Go app.

7. ‘Croupier’

The simple definition of a croupier is an individual who’s in charge of running a gaming table. The movie named after that important position follows an aspiring writer who takes on that role in order to support his ambitions. During his time spent as a croupier, he tries his hardest not to get sucked up in the dark world of gambling and fall for a more “attractive” temptation. He eventually succumbs to his dark desires and ends up in a situation far worse than he could have ever imagined.

Croupier can only be seen on Blu-Ray and DVD at the moment.

6. ‘House of Games’

A psychiatrist by the name of Margaret Ford is in the midst of helping a suicide victim confront his troubles head-on. Margaret’s patient is a man named Mike, who apparently works as a bookie. Due to their interactions, Margaret’s interests in the seedy world of high-stakes gambling intensify and lead to her becoming engulfed in the mental trickery that’s utilized in order to win big. But things take a turn for the worst when it turns out that Mike is nothing more than a con man, which puts Margaret into some harrowing situations.

House of Games can be viewed on iTunes, Vudu and Amazon Prime Video.

5. ‘The Sting’

The Sting is a classic film that’s the perfect onscreen representation of what it takes to pull off a major con job. The movie follows two fellow conmen that decide to get revenge on a crime boss who’s responsible for the death of their mutual acquaintance. The two men concoct a fail-proof plan that starts out easy enough but soon gets harder and harder to maintain as unexpected elements enter the picture. A whole lot of big bets, plus plenty of surprising twists and turns come to pass in this film that’s all about pulling one over on an unsuspecting victim.

The Sting can be seen on YouTube, iTunes, Google Play Movies & TV, Vudu, and Amazon Prime Video.

4. ‘Casino Royale’

The most efficient British Secret Service agent the world has ever seen takes on an especially dangerous mission in Casino Royale – take down Le Chiffre, a man who’s actually a financier for terrorist organizations. James Bond goes undercover in order to infiltrate Chiffre’s major poker game, which is secretly being used as a way to acquire even more funds to support his terrorist dealings. Bond goes all in order to put a stop to Le Chiffre’s plans and take down his evil organization in one fell swoop.

Casino Royale can be seen Amazon Prime Video, YouTube, Vudu, iTunes, Hulu, HBO Now, and HBO Go.

3. ‘California Split’

Charlie Waters and Bill Denny are gamblers who come together through a mutual appreciation of their hobby. Charlie goes out of his way to gamble as much as he can in a bid to win the biggest payday there is alongside Bill. Both men are granted lucky wins here and there, but a series of downturns and unfortunate mishaps threaten to destroy their gambling streak. California Split follows both men on their wild journey as they look to truly hit the jackpot.

This film can be seen on Vudu, iTunes and Amazon Prime Video.

2. ‘Bob le flambeur’

Translated as either “Bob the Gambler” or “Bob the High Roller,” Bob le flambuer is a cinematic breakdown of what happens when someone is forced to risk it all. Bob Montagne, the main character of the film, is known as an extremely lucky gambler who’s a big hit amongst the populace. But when things turn dour for him and his good luck subsides, the ones that once loved him the most decide to abandon him. In order to regain his wealthy status, Bob maps out a plan to rob a casino during a, particularly important weekend. But pulling off such a big heist is a lot harder than he expected it to be.

Bob le flambeur can be viewed on YouTube, iTunes, Google Play Movies & TV, Vudu, and Amazon Prime Video.

1. ‘The Hustler’

Remember us mentioning The Color of Money on this list beforehand? The Hustler should be seen first as it is the predecessor to that other highly recommended gambling film. The Hustler charts the early origins of “Fast Eddie” Felson and his days as a notorious poolroom hustler. Throughout the film, viewers will get to see Eddie play against a billiards champion, fall in love with a woman with plenty of emotional baggage and come into contact with an experienced gambler who wishes to take Eddie under his wing. The stakes are truly raised within this classic film when Eddie decides to go all in during a high-stakes matchup.

The Hustler can only be seen via DVD.

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