Best 10 Gambling Movies of All Time

Dec 19, 2019 Artyom Ustinov
Film directors often find inspiration for their movies in casinos across the world. While some of them have featured casino rooms in only a scene or two, others have made movies that revolve around the world of gambling.
If you’re a movie buff who wishes to explore the thrills of gambling and also learn about its risks, you’re in the right place. We’ve made a list of the top 10 movies that have entered the history and are regarded as the best gambling movies of all time.

1. Rounders

Rounders is widely regarded as one of the best gambling movies ever. It tells a story of a reformed gambler played by Matt Damon who gets dragged back into the world of gambling in order to help his friend, Edward Norton, pay off his loan shark debt.

The final poker duel between Matt Damon and Teddy KGB, played by John Malkovich, entered history as one of the best poker scenes ever filmed.

Rounders

2. 21

21 is based on a book written by Ben Mezrich, and it follows a true story about six MIT students who were trained to count cards and won millions from various casinos. While there are many fictional scenes, the movie perfectly depicts how money corrupts and how quickly the team falls apart.

It features stars like Kevin Spacey, Laurence Fishburne, Liza Lapira, and Jim Sturgess in the leading role as Ben Campbell who joined the team to pay for his tuition for Harvard Medical School.

21

3. Casino

With stars like Robert De Niro, Sharon Stone, Joe Pesci, and Martin Scorsese as the director, Casino quickly climbed the list of the best gambling movies of all time.

The movie follows the story of Same Rothstein, played by De Niro, and talks about the issues he faces running a casino, the involvement of the Mafia in the gambling business, and how his life changed over the years together with the city of Las Vegas.

Casino

4. Rain Man

Rain Man follows the story of two estranged brothers, Charlie Babbitt (Tom Cruise) and Raymond (Dustin Hoffman) who are reconciled after a long trip across the country.

Charlie is only interested in the money and getting the fortune his father had left in his will, while his brother Raymond, an autistic savant and expert in counting cards, only wishes to have a relationship with his brother.

While gambling plays only a small part in the movie, it shows how family ties are more important than easy cash, making it one of the must-watch movies.

Rain Man

5. The Gambler

The Gambler hit the big screen in 1974 and told a story of Axel Freed, a literature professor who has a gambling addiction. On the outside, Axel lives a normal life and is admired by his family, but what nobody knows is that his addiction has gotten him into serious debt with a local loan shark.

The movie beautifully depicts the dangers of gambling and shows how Axel, even after getting enough money to pay off the loan shark Hips, succumbs to his addiction and sinks in deeper into the world of gambling.

The Gambler was remade in 2014. The remake features Mark Wahlberg in the leading role and Rupert Wyatt as the director.

The Gambler

6. The Cincinnati Kid

The Cincinnati Kid is an American drama film from 1965 based on a novel by Richard Jessup. It follows Eric Stoner, also known as the kid, who is passionate about poker and driven to establish himself as the best poker player of his time.

To achieve that, he sets on a journey where he will have to challenge Lancey Howard, the best player, and strip him off his title. The movie features Steve McQueen, Edward g. Robinson, and Ann-Margret, and is directed by Norman Jewison.

The Cincinnati Kid

7. Ocean’s Eleven

While Ocean’s Eleven is directly related to gambling, the movie revolves around casinos, their day-to-day operations, and, of course, how to rob them. The movie was made in 2001 and tells a story of Danny Ocean, played by George Clooney, who assembles a crew to rob not one, but three casinos at the same time.

Apart from Clooney, the movie features many other Hollywood superstars such as Brad Pitt, Matt Damon, Andy Garcia, and Julia Roberts, and due to its sheer popularity also has several sequels worth checking out.

Ocean’s Eleven

8. High Roller: The Stu Ungar Story

Unlike many other movies on our list, High Roller: The Stu Ungar Story is a biography of Stu Ungar who was, and still is, regarded by many as the greatest Texas Hold’em poker player in history.

The biopic portrays Stu’s life from early years to his third victory at the WSOP Main Event that happened a year before his death and includes all the joys and hardships of life that come with being a professional gin and poker player.

High Roller: The Stu Ungar Story

9. Two for the Money

Two for the Money takes us away from the world of casinos and tells us what happens behind the curtains of sports gambling.

It tells a story of a college football star who takes a job handicapping football games after suffering a career-ending injury. After major success, things quickly go south for him, and he is left reevaluating his ability to predict games and ends up relying purely on luck.

The movie was released in 2005 and it features Al Pacino, Matthew McConaughey, and Rene Russo as the leading roles.

Two for the Money

10. Owning Mahowny

Owning Mahowny is a movie about the dangers of gambling addiction. This Canadian masterpiece follows a bank employee called Dan Mahowny, played by Philip Seymour Hoffman, who is a compulsive gambler and keeps sinking deeper and deeper into the world of gambling.

The movie depicts the domino effect gambling has on his life as he starts skimming millions of dollars from the bank he works at to fuel his gambling problem.

Owning Mahowny
Artyom Ustinov

Artyom is Head of White Label & Turnkey Solutions and has been working in complex B2B/B2C sales, as well as business development and management consulting in iGaming for more than 10 years.

Together with the Key Account Management Team, he has helped over 100 start-ups and experienced gaming companies to launch their projects with SoftGamings.

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