Greatest Gambling Movies of the Last 20 Years


Gambling movies have been a reliable staple for what seems like forever. So many have been made since the 1960s that it can be tough to pick just a few that help show off the best the genre has to offer. That’s why we decided to focus just on movies that have been released since 1996, which still gives us almost more than we can handle. These are a few of the great gambling movies that have graced our screens in the last two decades that we’d recommend taking a chance on.

The Gambler

This remake of the 1974 film of the same name stars Mark Wahlberg in the title role and also features the talents of 2016 Best Actress Oscar winner Brie Larson. It doesn’t quite manage to pack the same punch as the original James Caan vehicle, but it makes wonderful use of a terrific cast that also features screen legend Jessica Lange, John Goodman and Michael Kenneth Williams from “The Wire.” “The Gambler” is definitely one of the few remakes that is actually worth your time and is absolutely one of the best gambling films of the past several years.

Mississippi Grind

“Mississippi Grind” was a surprise hit last year when it was released directly to on-demand services to an incredible amount of critical acclaim. Ryan Reynolds set up a slow burn en route to taking over the cinematic landscape six months later with “Deadpool.” Ben Mendelsohn was also terrific, coming off his impressive turn in the Netflix original series “Bloodlines.” “Mississippi Grind” is not only the best gambling movie of the past year, but probably one of the best movies of 2015 that you never saw. Do yourself a favor and make sure to see this one as soon as possible, because it’s a modern gambling classic.


Martin Scorsese’s “Casino” is also known as “Goodfellas Do Vegas,” and that’s not necessarily a bad thing, as “Goodfellas” is objectively one of the greatest movies ever. With Robert De Niro, Joe Pesci and Sharon Stone all putting in some of the best performances of their careers, it’s no wonder that it’s considered the best gambling movie of all-time. Stone even received an Academy Award nomination for Best Actress. “Casino” is an epic of excess and stands out as a one of Scorsese’s best in a career that’s loaded with amazing movies.


“Rounders” is the quintessential classic poker movie. This movie came out a year before both “Fight Club” and “American History X,” and was a crucial step along the path to making Edward Norton and Matt Damon household names. In many ways, “Rounders” was largely responsible for the massive resurgence in the popularity of Texas Hold ‘Em poker in the United States – also known as the poker boom – and it quickly became a classic for card players everywhere.