Top 10 Gambling Movies of All-Time

Every time you buy a ticket at the theatre, you question yourself will it be worth the money and time? There’s always a risk when picking a movie, but gambling movies always include inherent drama because, by definition, they are always about risk.

You don’t get joy and excitement from watching someone be cautious and safe, but there is a lot of thrill in watching someone put everything on the line.

Gamblers in casino movies are always going for that one big score. So if you are looking for the best gambling movies, then you are at the right place. Below are our recommended top 10 gambling movies about casinos, along with their cast and plot.

10. Croupier (1998)

Croupier is a 1998 British movie directed by Mike Hodges and starring Clive Owen and Kate Hardie as main characters.

In the story, Jack Manfred is shown as a struggling novelist in London. To pull off his minimum necessities, he sells his car and, using his father’s South African connections, gets a job as a croupier at the Golden Lion Casino, which happens to be a second-tier casino in London. He had previous training in South Africa.

Jack doesn’t like playing, but since he is good at being a croupier, he dives into that role. His girlfriend Marion, who also happens to be an ex-police officer, doesn’t like his job despite the considerable money it’s bringing to the household.

The casino has some strict policies like no gambling for staff, no relationships with other casino employees, and no consorting with gamblers.

Although Jack cannot cheat, he is not against bending these employee rules according to his needs. As time passes, Jack allows an alter ego, “Jake,” and allows Jake to do things he would never be able to do himself.

Jack, when asked by Jani, a gambler he likes, to be the inside man for a planned heist at the Casino, Jack thinks it is straightforward. Even a professional like him fails to predict the cards he will be dealt.

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9. 21 (2008)

21 is a 2008 American movie directed by Robert Luketic and starring Kavin Spacey, Jim Sturgess, Kate Bosworth, and Laurence Fishburne as main characters portraiting a real story of the MIT blackjack team.

Ben Campbell is a brilliant student at M.I.T, Boston, striving to succeed. He wants to become a doctor and a scholarship to transfer to the Havard School of Medicine. Ben knows he cannot afford the fees for the four to five years of schooling at Havard as he was from a poor, working-class family.

One evening, Ben’s unorthodox maths teacher Micky Rosa introduces him to a club of five – Jill, Choi, Kianna, and Fisher trained by Professor Rosa in the skill of card counting.

Intrigued by the desire to make money, Ben joins this small group of people on weekend trips to Las Vegas, where they would win hundreds of thousands of dollars in blackjack by just using their skills of code talk and hand signals.

Initially, Ben wanted to make only the money he needed for his schooling at Havard. But Ben lives up to Jill’s prediction and becomes corrupted. He gets clouded by greed and arrogance, letting his feelings in the way and endangering the group on the radar of a brutal casino security enforcer, Code Williams.

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8. Ocean’s Eleven (2001)

Ocean’s Eleven is a 2001 American heist comedy directed by Steven Soderbergh with George Clooney, Brad Pitt, and Matt Demon as the main characters.

After being released from prison, Danny Ocean violates his parole and travels to California to meet his partner and friend to propose a heist. Then the two go to Las Vegas to propose the plan to wealthy friend and former casino owner Ruben Tishkoff. The plan was to rob the Bellagio, the Mirage, and the MGM Grand casinos simultaneously.

Although Ruben is reluctant to get involved at first, he quickly agrees as soon as he sees it as a chance to take revenge on his rival, Terry Benedict, who owns all three casinos. They recruit eight former colleagues and criminal specialists.

Next, they conduct surveillance at the Bellagio to learn about the casino staff’s security, routines, behavior, and building infrastructure. They even prepare a dummy vault precisely similar to the original one.

On the night of the execution, they accurately carry out the plan. They trick Benedict and his bodyguards into thinking they flew with half the money making the guards chase them in a van. In the meantime, they arrive as a SWAT team and steal all the money right under Benedict’s nose without realizing it.

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7. Molly’s Game (2017)

Molly’s Game is a 2017 American biographical crime drama written and directed by Aaron Sorkin. The movie stars Idris Alba and Jessica Chastain as lead actors.

Molly Bloom is a world-class Mogul skier who is expected to go and win in the Olympics. She was severely injured in a quality event for the 2022 Winter Olympics, ending her career. She moved to Los Angeles to make a fresh start rather than attend law school. There Molly finds interest in running a high-stakes poker game for extremely wealthy celebrities.

This is how an influential poker hostess was born. She ran the world’s most exclusive high-stakes poker game for over a decade until she was finally arrested. Her only support or ally was her defense lawyer Charlie Jaffrey.

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6. Mississippi Grind (2015)

Mississippi Grind is a 2015 American comedy drama movie written and directed by Anna Boden and Ryan Fleck. The movie features Ryan Reynolds, Ben Mendelsohn, and Sienna Miller as leading characters.

Down on his hardships, Jerry, a struggling gambler and real estate agent, teams up with a younger gambler Curtis in a casino in Dubuque, Iowa. Gerry proposes to Curtis a gambling trip down the Mississippi, climaxing in a casino in New Orleans. Gerry goes on to gamble in each Casino, where he loses and asks for money from Curtis.

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5. Rounders (1998)

Rounders is a 1998 American drama movie directed by John Dahl and stars Matt Demon and Edward Nortan as lead actors.

Mike McDermott (Matt Damon), a law student, loses his entire savings to Russian club owner Teddy KGB. Then he decided to give up gambling and turn his attention toward studies and his live-in girlfriend, Jo. She was worried about the time when Mike’s old gambling mate Worm would come out of prison.

It was pretty evident of her to be worried as it would Worm only a couple of minutes to pull Mike back into the gambling world and casinos. Mike eventually does that too. When Jo finds out that Mike has again started going to poker clubs, she moves out, and Mike begins to lose interest in his studies.

The Worm has a prison debt, and the threatening Gama wants his money back. Mike gets involved in Worm’s debt. When Gama demands his enormous amount of money in a five-day deadline, the two old gambling buddies set out on endless gambling without sleep. This gambling binge goes downwards, leading them to face Teddy KGB.

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4. The Cincinnati Kid (1965)

The Cincinnati Kid is a 1965 American drama movie directed by Norman Jewison and features Steve McQueen, Edward G Robinson, and Ann-Margret as leading actors.

The movie is based in 1930’s New Orleans when there were no online casinos, and everyone was gambling in local rooms. Eric Stoner, or the Cincinnati Kid in his known circle, was an upcoming gambler, especially in poker. When Lancey Howard, known as the best in poker, comes to town, the Kid wants to play him and win so that people might know his name, and it would add a lot of glory to his name.

The Kid’s friend Shooter arranges the game. In the build-up to the game, the Kid faces many hurdles as his girlfriend, Christian, wants more commitment from him. The Shooter’s sluttish wife lets out that she is willing to cheat on Shooter just like she cheats on everything.

William Jefferson Slade tries to blackmail Shooter into designing the game in the Kid’s favour as he wants to get back at Lancey, and all of this ends with a bang.

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3. California Split (1974)

California Split is a 1974 American drama-comedy movie directed by Robert Altman and stars Elliott Gould and George Segal as leading actors.

Ben Gilly and Charlie Walters become friends at the gambling table after getting beaten and robbed by a card player whose money they have won. Charlie is an experienced gambler constantly looking for the next big score. Bill is a full-time magazine writer and not a committed gambler.

The more the two hang out, the more Bill gets addicted to the gambling lifestyle. He wants to live a life like Charlie, especially hang out with prostitute friends like Barbara Millers and Susan Peters. In his quest for a gambling life, Bill becomes a debt to his loan shark.

He gives up possession, including his car, to fund a bus trip to Reno. On the way, Charlie spots the man who robbed them at the film’s beginning and gets some revenge. On their way home, Bill and Charlie pool their money, and Bill wins. Bill starts to think he is on a hot streak, so he keeps playing and winning more. But how does all of it end?

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2. The Gambler (1974)

The Gambler is a 1974 American crime drama movie directed by Karel Reisz and features James Caan, Burt Young, and Paul Sorvino as leading actors.

Axel Freed, an English professor at New York College, is a gambling addict. His gambling has left him in massive debt. He owes a lot of money to his loan shark. When Billie, his girlfriend, comes to know Axel is in such debt, she questions her wisdom in being with him. Axel tells her that he loves the dangers of his life.

To take care of his finances, Axel tries to bribe a star player of his college team to give up the match and also pays him money. The student accepts. He spends the night celebrating when he wins the match, and the money after his team gives up 10 points.

He sleeps with a prostitute, but because of his weird behavior, she thinks he is crazy and slashes him with a switchblade, which starts another round of drama.

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1. Casino (1995)

The Casino is a 1995 American epic drama movie directed by Martin Scorsese and features Robert De Niro, Joe Pesci, and Sharon Stone as leading actors.

Bookie and handicapper Sam Rothstein, also known as Ace to his friends, conforms to the law when the Italian mafia hires him to the Tangiers Casino on the Las Vegas Strip. Ace makes a success of the Casino.

Now the mafia bosses can take profits off the top while making the business seem entirely legitimate. Ace’s success is jeopardized by his childhood friend Nicky and his wife, Ginger McKenna, which adds another twist to the epic gambling movie you must see.

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