20 Greatest Gambling Films That Are Truly Epic

Taking a break from playing the slots or a card game can be challenging, especially if you are a winning streak. But, if you need a break to recharge or even just need to try and get inspiration to get your winning streak back, there is no better way to do so then by watching a movie about casinos and winning (or losing!) it all. Here are 20 of the greatest movies about gambling to watch this weekend.

1. Casino Royale (2006)

Played by the dashing Daniel Craig, James Bond is back as our favourite 00 Agent. On yet another dangerous mission, he is up against the banker of the world’s terrorists. In the ultimate and stressful showdown, Bond is in a fight for his life at a high stakes poker game in Montenegro. Everything is on the line, and he must win all his money back by defeating Le Chiffre, played by the actor Mads Mikkelsen. If he succeeds in taking down the terrorist’s banker, does that mean James Bond can save the world and stay safe himself?

2. The Hustler (1961)

Pool hustler “Fast” Eddie Felson, played by Paul Newman, is the frontman in this Academy-Award-winning film. Fast Eddie mixes talent with a reckless attitude as he starts small, taking lower-skilled players on before moving on to tackle the top billiards player Minnesota Fats (Jackie Gleason). Despite losing, Fast Eddie is still determined to win, and quickly becomes obsessed with it. He eventually falls in with an experienced gambler Bert Gordon (George C. Scott) as well as a lonely woman, Sarah (Piper Laurie). Will Eddie be able to take on Minnesota and win despite the outside distractions?

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3. Ocean’s Eleven

11 guys. 150 million dollars. One amazing heist. Danny Ocean (George Clooney) concocts a scheme to rob, not just one, but three of Las Vegas’ biggest casinos: The Bellagio, the Mirage, and the MGM Grand casinos, all owned by the ruthless Terry Benedict (Andy Garcia). Of course, the robbery won’t be easy, and assembling the right team of men is essential to achieving their goal and walking away with millions. However, as they get deeper into the scheme, they start to realize that maybe they aren’t all trying to get the same thing. Will they be able to overcome their differences and pull off the biggest Vegas scam of all time without getting caught?

4. Casino Tycoon (1992)

Set during World War II, Casino Tycoon follows a young graduate named Benny (Andy Lau) who flees to Hong Kong after the Japanese invasion. He immediately heads to Macau—a gambling haven. Once there, he quickly meets and impresses a businessman who has connections with the organized crime world. As Benny works his way up through the ranks of the seedy underbelly of Macau, he gets into a lot of trouble along the way.

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

High Roller: The Stu Ungar Story is one of the best biographical gambling movies you can watch. Stu “Stuey” Ungar (Michael Imperioli) plays a high-roller poker player. As the only poker player to win three WSOP Main Event Tournaments, Stuey seems to have it all going for him… until he doesn’t. This film shows the sometimes painful breakdown of a man who once had it all. It depicts not only the insane highs but the terrible lows. The journey of Stu Ungar’s rise to fame, and then dramatic fall is tragic at times, but it is also a must-watch film.

6. Rounders (1998)

A young Matt Damon plays law student Mike McDermott who dreams of one day winning the World Series of Poker. He can’t resist the countless New York private clubs that host high-stakes poker games. At an underground game hosted by a Russian mobster, Teddy “KGB” (John Malkovich), Mike loses his entire bankroll of $30,000 in just a single hand of Texas hold ‘em. Embarrassed and shaken, Mike promises his girlfriend Jo (Gretchen Mol) that he will quit poker for good and concentrate on his studies. And for time, he keeps to his word, until his childhood friend Word (Edward Norton) is released from prison and racks up thousands of dollars of debt in Mike’s name. With KGB after him, Mike now must return to the world of poker to pay off the debts… and survive.

7. The Gambler (1997)

James Caan plays Axel Freed, a popular college professor who seems to have everything going for him. The only catch – he is addicted to gambling. His wins and losses yo-yo back and forth; he wins big on the one hand, just to lose it all on the next. As he becomes addicted to getting that next big win, he sinks lower and lower into debt. He borrows money from everyone he knows: girlfriend, rich mother, and even a loan shark. Unable to pay off his debts, Axel’s life further deteriorates when his girlfriend leaves him, and his mother disowns him. With the mob on his tail, he decides to play one last hand to win it back his dignity.

8. The Cincinnati Kid (1965)

Even though this is an older film, it still deserves its spot on some of the best gambling movies ever. Set in the 1930s in New Orleans, the movie follows the story of Eric “the Kid” Stoner, a young poker player who is determined to make a name for himself as the best poker player in town. Up until this point in his journey, The Kid has been successful bouncing from town to town, winning hands. However, when he arrives in New Orleans, he meets the legendary card-shake Lancey “The Man” Howard, played by Edward G. Robinson. The movie ends with a final poker showdown between these two legendary players.

9. 21 (2008)

Based on true events, 21 follows the story of MIT student Ben Campbell (Jim Sturgess). Short on cash to pay his tuition bills, Ben decides to team up with some of his fellow students, who are led by Professor Mickey Rosa (Kevin Spacey). By using their math skills to count cards and scam casinos, the team of crafty students is able to win a massive pile of cash in Las Vegas. Ben starts to lose sight of his goals after being seduced by his teammate, played by the beautiful and smart Kate Bosworth. As his successes begin to pile up, Campbell starts to realize how high the stakes are, especially after he has unpleasant run-ins with casino enforcer Cole Williams, played by Laurence Fishburne. Will Ben be able to extract himself from the world of poker, or will he jeopardize his future and education?

10. The Sting (1973)

Robert Redford plays a small-time con man, Johnny Hooker, who usually doesn’t try to rock the boat too hard. However, when he accidentally steals from the vindictive crime boss Doyle Lonnegan (Robert Shaw), Doyle immediately retaliates by killing Johnny’s partner. Johnny now is after Doyle, trying to avenge his partner’s death, but not through murder, but instead by hitting Doyle where it will really hurt him: his wallet. Johnny joins forces with a veteran con man Henry Gondorff (Paul Newman) to pull off the greatest con of all time. Even though the stakes are high, the potential payout makes it worth the risk. Now, the only question remains is, will they succeed?

11. Casino (1995)

Las Vegas is home to many nefarious and questionable individuals, which means illegal things often fly under the radar. The seedy underbelly of America’s playground attracts two mobsters, Ace Rothstein (Robert De Niro) and Nicky Santoro (Joe Pesci), who want to leave a lasting mark at the casinos. Set in the ’70s and ’80s, the two mobsters are the ones who are running the casinos. Instead of trying to beat the odds, they are the ones who set the odds. For a time, everything seems to be going according to plan, until Rothstein marries Ginger, a drug-addicted hustler played y Sharon Stone, as well as thoughtless actions committed by the aggressive and violent Mafia boss Nicky Santoro (Joe Pesci) that destroys the empire they were creating.

12. Lock, Stock, and Two Smoking Barrels (1998)

Card-shark Eddy (Nick Moran) has been hustling for years. After learning about an illegal high-stakes card game, he immediately signs up. The card game, hosted by “Hatchet” Harry (P.H. Moriarty), is fixed by the crime boss, and Eddy discovers that he owes 500,000 pounds. Desperate for cash, he overhears his neighbours talking about a scheme against some neighbourhood drug dealers. Together with three of his friends, Eddy launches his own messy and poorly planned heist in an attempt to raise money to pay back Harry. Their journey takes them to unexpected places and through a series of strange events.

13. Ocean’s Thirteen (2007)

As the third instalment in the Ocean’s series, we meet back up again with Danny Ocean (George Clooney) and his crew members. After Willy Bank (Al Pacino) double-crosses one of their members, Reuben Tiskhoff, the gang knows they must act to save him. Once again, the original eleven team up to take down a seemingly unbeatable force. This time, the goal is to destroy Bank’s reputation as the sole hotelier to have earned the prestigious Royal Review’s Five Diamond award at not just one of his properties, but all. Will Ocean and his crew have it in them for one last battle?

14. Hard Eight (1996)

Professional gambler Sydney (Philip Baker Hall) is in his sixties when he meets a young man John (John C. Reilly) by chance. John is in a bad spot and has just lost everything in Las Vegas after trying to win money to pay for his mother’s funeral. After taking pity on the young man, Sydney decides to teach him a few tips and tricks, including how to get a free room and dinner for the night. The story progresses, and more than two years down the road, John is still learning from Sydney and living in Las Vegas. By now, he is falling in love with a cocktail waitress named Clementine (Gwyneth Paltrow), who is also a prostitute on the side. John’s relationship with Cleminite starts to cause unrest between the two men, which might put their entire scheme at risk.

15. Rain Man (1988)

Tom Cruise plays Charlie Babbitt, a self-absorbed man who has never cared about anything other than himself. After his estranged father dies, Charlie is stunned to discover that his father didn’t leave him even a penny. Instead, all the money went to Charlies’ autistic brother, who he never really knew. Played by Dustin Huffman, Raymond is heavily focused on academics and is the exact opposite of Charlie. In an attempt to get at least some of the inheritance, Charlie decides to take his brother out on a trip to the west coast. During a stop at Las Vegas, Charlie sees an opportunity to put his brother’s academic talents to good use.

16. House of Games (1987)

Margaret Ford (Lindsay Crouse) is a famous psychologist who wants to assist one of her patients with paying off a substantial gambling debt. However, she quickly realizes she is out of her league. While visiting with her patient Mike (Joe Mantegna) at the same bar where he owes the massive debt, she realizes that there are poker games running, and she has a hidden talent – noticing the “tells” or give-away signs of the opposing poker players. Mike convinces Margaret to use her exceptional talent to help him beat out the other players. While the job seems easy enough, will she be able to succeed?

17. Croupier (1998)

One of the most stylish gambling movies, Croupier is also unconventional. The events of the film follow the main character Jack Manfred who is an aspiring writer and moonlights as a casino croupier, despite not gambling himself. However, the longer he stays on the job, the more he starts to realise that life is a game of chance. As he watches gamblers throw away hundreds and thousands of dollars at the card tables, you start to see his cold and cynical side start to come out.

18. Molly’s Game (2017)

Based on a memoir of the game name, Molly’s Game follows the story of Molly (Jessica Chastain), who is a world-class skier who dreams of competing in the Olympics. However, during a qualifying event, Molly is severely injuring, destroying her dreams. Molly decides to take a year off and moves to Los Angeles and becomes a bottle service waitress, and soon gets involved in underground poker games. As Molly meets more people, she starts to earn vast amounts of money in tips. As she gets further into the world, Molly starts to host her own games that include members of the Russian mafia. Eventually, her tournaments are raided, and Molly has to choose to decide if she wants to become an FBI-informant and risk angering the mob.

19. Win It All (2017)

A Netflix original movie, Win It All, is about Eddie Garrett (Jake Johnson), a parking attendant outside of Wrigley Field who is addicted to gambling. One day, his acquaintance Michael asks him to watch an unopened bag for him while he is in prison and will reward him $10,000 once he gets out. Eddie’s curiosity gets the best of him, and he discovers the bag is full of cash. He can’t resist and begins to gamble with the money and, at first, is successful. However, he starts to lose money and quickly realises he is in too deep and can’t pay back the bag unless he takes drastic actions. Can he make the money back in time before Michael is released from prison?

20. The Grand (2007)

If you are in the mood for something a little lighter and funnier, then The Grand should be your go-to film. It is set in the world of professional poker players and follows the journey of six different players who all reach the final table of the Grand Championship. Woody Harrelson plays Jack Faro, who plays a recovering drug addict who is so unsuccessful at quitting drugs, he decided to move into a rehab centre permanently. He is also a serial husband and has been married an astounding 75 times. He enters the tournament to win the huge prize to help keep his grandfather’s casino open. The other players all consist of hilariously strange people who make the tournament unforgettable.

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