The Best Gambling-Themed Movies to Watch

Gambling movies have slowly become some of the best films ever to be released. While they often don’t have the same action and explosions as major box office hits, they are still definitely worth watching.

Some are Oscar winners, others put famous names on the map, and some are so unbelievable that it is hard to believe they are based on actual events. This list will go through some of the best gambling movies to watch right now. 

21

21 is a true, albeit embellished, story about a group of MIT students who not only learned to count cards but developed a system that won them millions of dollars for over a decade without being caught.

While there can be moments with a bit too much action, there is a lot of math and talk about the science behind gambling. There are also a couple of twists that you may or may not see coming. Either way, it’s a brilliant gambling-based movie.

Ocean’s 11

While the originals are good, the Ocean’s franchise skyrocketed in popularity due to the remakes. George Clooney and Brad Pitt are crooks and conmen that lead an ensemble cast in robbing a casino. Not only that, but the casino is owned by Clooney’s ex-wife’s new man.

The movie has action, intrigue, an edge-of-your-seat story, a cast that clicks together, and is topped off with a number of genuinely funny moments. The sequels, while not as great as the original, are also very entertaining to watch.

Molly’s Game

Molly’s Game is based on the life of a former Olympian hopeful, Molly Bloom, who travels to Los Angeles after a career-ending injury and finds herself as an assistant to a businessman who runs illegal poker games for the rich and famous.

This whirlwind journey sees Molly begin running games for Leo Di Caprio, Ben Affleck, Matt Damon, sports and music stars, and multi-millionaires from across the US and the world. She even gets tied up with the mob at one point.

This is undoubtedly a nail-biting film as the stakes ramp up, both in the game and Molly’s real life.

Rounders

Rounders is not only one of the best representations of what it was like to be a professional poker player in the 90s, but is also the movie that got Matt Damon hooked on the game he still plays regularly today.

Damon is not the only star in the movie either; John Malkovich joins him, John Turturro, Martin Landau, Famke Janssen, and Bill Camp. It’s a bit grimy, a bit arrogant, but a must-watch for poker-lovers and newbies alike.

Hard Eight

Hard Eight tells the story of a lonely, unassuming man trying to survive in the lights and misery of Las Vegas. While he lives in the shadows, his life is turned around when he encounters people who genuinely need his help.

Hard Eight is less glamorous than most movies associated with gambling, casinos, and Las Vegas, but it’s undoubtedly more real. There is also a scene by the legendary Phillip Seymour Hoffman that is iconic at this point, and it’s worth watching this movie for this scene alone.

Uncut Gems 

A bit of a strange movie is Uncut Gems. Adam Sandler plays the role of a gambling-loving jeweler who smuggles a rare and incredibly expensive opal out of Ethiopia, which he will use to pay back gambling debt.

What unfolds is a race to find the opal before Sandler’s loan sharks start playing hardball. Sandler is often criticized for playing goofy characters in movies that are flops, but Uncut Gems is, ironically, a diamond in the rough.

California Split

California Split is a 1974 gambling movie featuring Elliot Gould and George Segal, two gamblers who find friendship after being beaten up by card players when they win and take their money.

The movie was the first non-Cinerama movie to feature 8-track audio, and it has been widely praised, mainly by Vulture.com, as the best gambling movie of all time. It has drama, a few heartwarming moments, and of course, comedy.

Rain Man

While Rain Man isn’t necessarily a film about casinos or gambling, there is an incredibly famous and extensive casino scene where Dustin Hoffman and Tom Cruise attempt to win the money needed to pay back some debts.

As mentioned, it isn’t a gambling movie, but the casino scenes are amazing, the story is fantastic, and whether you are a gambling movie lover or not, Rain Man is a must-watch.

Casino

Casino is a 1995 epic crime drama that features a cast consisting of Robert De Niro, Sharon Stone, Joe Pesci, Don Rickles, Kevin Pollak, and James Woods. Directed by Martin Scorsese, it is the eighth collaboration between Scorsese and De Niro.

De Niro, a man working for the mob, is asked to oversee the Tangiers casino. The film explores the difficulties of the casino, the involvement of the Mafia, and his relationships with the other characters. The film is loosely based on real people and events, but they are highly glamorized for the big screen.

The Sting

The Sting is a 1973 caper film starring Robert Redford and Paul Newman, two grifters who begin an elaborate and complicated plot to con a mob boss, played by Robert Shaw.

The film was a massive success at the time; it was nominated for 10 Oscars at the 46th Academy Awards and won seven, including Best Picture, Best Director, and a Best Actor win for Robert Redford; it was also the catalyst for reigniting Newman’s career.

Tricheurs

A simple film, Tricheurs, tells the story of a man and woman who realize that no matter how hard you try and how smart you are, the only way to beat the casino and win some serious money is to cheat.

The foreign film was praised for its storytelling, showing what would happen if you get too greedy, spend your life constantly on the hunt for more, not knowing when to stop and enjoy what you have.

Even if you aren’t a gambler yourself, these are not only some of the best gambling movies of all time but some of the best movies of all time in general. Find the time to watch every one of them; you won’t be disappointed.