Best Gambling Movies of All Time

When it comes to movies, Hollywood draws inspiration for numerous sources, including gambling. In fact, there are dozens of classic gambling movies to choose from covering a broad range of gambling-related topics. From big budget movies with an all-star cast, to smaller independent films and biographical stories, there is no shortage of great gambling movies out there. 

The Cooler

The Cooler stars William H. Macy as Wayne Kramer, a man whose bad luck means good things for shady casino owners. He is hired to ruin the luck of players on a winning streak, but this soon changes and he becomes a lucky charm to the very players he is hired to sabotage. This doesn’t sit well with his casino employers and things start to take a turn for the dramatic. Featuring a stellar cast and a superb performance by Macy, this is a fun yet insightful look at the topics of luck and superstitions at casinos.

Rounders

Featuring Hollywood heavyweight Matt Damon in his younger days, Rounders is based on an entrepreneur who resorts to poker to pay his university tuition. Featuring an all-star cast, including Edward Norton and John Malkovich, the film is a stunning portrait of the gambling culture, including the strategy and banter that takes place at the poker table.

The Gambler

The Gambler tells the story of a gambling addict and university professor, played by the brilliant James Caan. The film tackles some serious issues as the titular character’s life plunges into danger as his addiction gets worse. This is a beautiful, intense movie that will appeal to gambling purists and highlights the dark side of gambling and addiction.

The Cincinnati Kid

This classic stars the legendary Steve McQueen. The Cincinnati Kid is an up-and-coming gambler who gets the chance to play high roller of the day, Lancey Howard. As his reputation as serious competitor grows, the Kid meets a love interest and this distraction threatens to blow his chances of winning. Watch not only for the excellent performances by for the thrilling finale.

21

Based on a true story, 21 is a tale of a maths professor, played by Kevin Spacey, who trains a group of talented students known as the MIT Blackjack Team to could cards at some of the biggest casinos in Las Vegas. The movie takes audiences on an epic, incredible journey as the group of youngsters trick their way into some massive wins. Expect lots of thrills and jaw-dropping moments.

Casino

Finally, Casino is likely the most famous gambling movies and stars Hollywood superstars Robert De Niro, Joe Pesci and Sharon Stone. The film depicts the seedier side of Las Vegas, where the mob controls Sin City’s gambling industry.  Casino is a thrilling masterpiece with some incredible performances and some of the most intense and harrowing scenes in film history. Another must-watch for all casino and movie lovers.

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