Top Five Gambling Movies of All-Time

America seems to love a good gamble and the folks in Hollywood are no different. Audiences have forever flocked to films where the protagonist throws caution to the wind and lays it all on the line, letting luck decide their fate. In fact, several gambling-themed films have become cult classics, and provided viewers some of the most magical moments in movie history.

With that in mind, we present the top five gambling-themed movies in Hollywood history, starting with a film about a horse, of course:

  1. Let It Ride

Let It Ride is a 1989 film starring Richard Dreyfuss as a cab driver who gets tip on a racehorse, wins big, and instead of banking the winnings, decides to let it ride, gambling his way through an unforgettable day at the track.

It’s a classic comedy and certainly a fun ride. Audiences can’t help root for Dreyfuss’ perennial underdog character as he tries to turn his life around and ultimately puts it all on the line time after time.

  1. Ocean’s Eleven

Director Steven Soderbergh’s 2001 remake of the 1960 Rat Pack classic, Ocean’s Eleven is really more of a heist film than a gambling-themed movie. But since the ensemble cast that includes Hollywood heavyweights like George Clooney, Brad Pitt, Matt Damon, Don Cheadle, Andy García, and Julia Roberts plot to rob the world famous Bellagio casino in Las Vegas, it definitely qualifies.

Ocean’s Eleven is a slick and entertaining ride through the high-stakes gambling and casino world and its success spawned two sequels, including 2004’s Ocean’s Twelve and 2007’s Ocean’s Thirteen.


  1. The Sting

The Academy Award winner for Best Picture in 1973, The Sting stars Hollywood royalty Paul Newman and Robert Redford as a pair of grifters who set out to con a mob boss.

It’s a horse-racing con that ultimately helps these sharks sink their teeth into the whale and the film is steeped in the world of gambling and crime during the Great Depression. The movie also won Academy Awards for Best Director and Best Original Screenplay and remains as entertaining to this day as a gambling-themed movie can get.


  1. Rounders

Before Chris Moneymaker won the 2003 World Championship, poker boomed and a generation of online poker players were born, there was Rounders.

This 1998 film starred Matt Damon and Edward Norton weaving their way through the seedy world of underground card games in New York City. It did its best to make poker look cool and as the game’s popularity rose through the early 2000s, the film reached cult classic status, with quotes from its characters still being used almost daily in card rooms around the country, and indeed, the world.

  1. Casino

Martin Scorsese’s 1995 classic about the inner-workings of a Las Vegas casino and the roller-coaster lives of the people who run it is a likely candidate to top most lists of Hollywood’s best gambling-themed movies.


Robert De Niro stars as bookie and casino boss Ace Rothstein with long-time running mate Joe Pesci playing his best friend and mafia boss Nicky Santoro. The film gives an inside look into how things really ran in Las Vegas in the old days, and while the performances of De Niro and Pesci are top notch, they are perhaps surpassed by female lead Sharon Stone. Stone turned in a gut-wrenching performance as Rothstein’s wife that earned her the Golden Globe Award for Best Actress in a Motion Picture – Drama and an Academy Award nomination for Best Actress.

Casino is an epic casino saga that has held up as a Scorsese classic. When it comes to gambling-themed movies, Casino is a must see.


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