The Top 7 Movies on Gambling (And How Accurate They Are)

Casino Floor, Poker Cards Spread, Movies About Gambling
The good news about Hollywood movies is that they always accurately portray their subject matter and never, ever, take liberties to produce a better film.

Okay, clearly, that’s a lie. In fact, Hollywood is perfectly happy to do a little handwaving and play loose with the facts if it means that movie turns out better in the end.

This is fine, because everyone wants a good movie, even when the subject of the movie is gambling. If multiple hours of watching casino poker games on TV is any indication, it should be exciting enough.

However, Hollywood continues to make movies about gambling and plays with the details when it suits them. Therefore, we’ve compiled a list of the top gambling movies produced by Hollywood and rated them on how accurately they portray the activity.

Of course, compiling any top list of movies leads to a fair amount of debate. This list, pin particular, favors newer movies. This was done on purpose, because gambling as a whole has changed a lot over the years and newer movies are more likely to represent today’s form.

1 – Rounders

Rounders tops the list of movies on gambling for a number of reasons. First, Matt Damon and Edward Norton give gritty, no-nonsense performances that transport you directly into some shady poker rooms across the New England area. Plus, the movie itself is riveting.

Part of the attraction of the movie is just how real it feels. As Damon gets good hands, lousy hands, and everything in between, it’s pretty easy to see yourself in those situations feeling the thrill of a great hand and the disappointment of a poker hand gone wrong. Another part of what makes this movie great are the characters who feel very true to life.

Part of why the movie feels so real is the amount of research the screenwriters (David Levien and Brian Koppelman) did as they wrote the movie, coupled with the actual underground poker rooms Damon and Norton visited (according to ESPN).

In other words, Rounders feels real because a lot of it is based in the real world.

Of course, many of the characters in Rounders play larger-than-life versions of real people the screenwriters met and, this being Hollywood, liberties were taken. Still, despite that, this movie does a great job of putting you in the poker action.

2 – Ocean’s Eleven and Thirteen

Brad Pitt and George Clooney in Ocean's Eleven, Las Vegas Strip at Night
Ocean’s Eleven (and Thirteen) and whatever else comes out of the minds of directors Steven Soderbergh, actors George Clooney, Damon, and Brad Pitt, and others make the list because they are incredibly fun movies to watch and feature gambling in some form.

What Ocean’s Eleven gets right is the location shots of the City of Las Vegas, some of the commentary about casinos (they can be hard to navigate), and they are generally right about the lengths to which a casino will go to be secure while making up a lot of stuff along the way.

In general, Ocean’s Eleven and the sequels are more fiction than fact, but they’re fun. That’s why we keep them on the list. (Quick note: Neither Ocean’s Twelve nor Ocean’s Eight made the list because these movies were about heists, not casino heists.)

3 – 21

21 is the film adaptation of Ben Mezrich’s book Bringing Down the House. Both tell the story of a band of plucky MIT students who win loads of money using the awesome power of math. That description is only slightly hyperbolic.

In fact, the movie shows a mastermind bringing together smart MIT students who can quickly do the mental arithmetic to count cards. Working in teams, these students do end up winning a lot of money from the casinos before they are beaten up, their winnings are stolen at gunpoint, and lives are generally ruined.

The interesting part about 21 is that there are lots of little nuggets that are true about it. For example, the system for counting cards is basically a legitimate way to make money.

This system is described in greater detail in the book and can work if a team is willing to play together to beat the odds.

Unfortunately, the rest of the movie is just a Hollywood heist/revenge movie that’s good for passing an evening.

4 – High Roller: The Stu Ungar Story

Crowd at WSOP tournament, High Roller The Stu Ungar Movie Poster
Stu Ungar was a highly-intelligent, controversial figure in the world of gin and poker. His early childhood as the son of a bookie led to wins in underground card games and eventually three World Series of Poker championships. His role is portrayed by Michael Imperioli (of Sopranos fame) in High Roller: The Stu Ungar Story.

As a movie, it’s a bit all over the place. Critics say that it focuses too much on his achievements while glossing over his drug addiction, gambling addiction, and barely touches on some odious personal habits that undoubtedly got him in trouble (like not following the unofficial rules of poker, which got him in trouble with more than a few players).

With that said, the poker action itself feels real enough to give poker fans something to chew on, but it could definitely have done more to showcase the game. Still, despite all of these flaws, it is a great movie that sheds light on one of poker’s all-time winningest players.

5 – Two for the Money

Two for the Money is a book about the rise and fall of Matthew McConaughey’s Brandon Lang, as he is hired, then betrays, then makes up with Al Pacino’s Walter Abrams before taking a job coaching Little League. If that sounds bizarre, that’s because it sort of is, especially when a very upset C.M. Novian (played by Armand Assante) ends up urinating on Lang for making bad picks.

Even as I type that, I’m having trouble making sense of the plot of this film, and I saw it in the theaters. Regardless, Two for the Money is a biographical tale based on the real Brandon Lang who forewent the exciting life of Little League coach to stay in sports betting and work as a handicapper.

All jokes aside, Two for the Money is a pretty good film that showcases both Pacino’s and McConaughey’s talents. There’s also plenty of little tidbits one can take away about how handicappers work, especially at the beginning of the film before McConaughey’s character essentially decides to give up. Definitely give it a watch.

6 – Casino

Scene From the Movie Casino, Two Red Dice
Casino makes the list because it’s one of the all-time greatest movies no matter the genre, and it also features casinos. This film is a fairly good look into how casinos were run back in the day, though in a lot of ways, the violence was toned down compared to what really happened.

Still, Casino is more a mob film than a true gambling film. We just really liked it and thought it deserved to be on the list.

7 – Maverick

We debated putting this Mel Gibson vehicle on the list, but in the end, it’s just too much fun not to include. This movie really does focus on poker in the Old West in a number of ways.

Although, for the first half, the poker action is largely off camera and only serves to establish the main character’s superhuman ability to take everyone’s money playing the game.

Later, the movie chronicles the main character—Maverick—and his ascension to the final table in a game of poker. He bets everything on the top card of a deck that had been dealt from by a crooked dealer. Of course, Maverick wins and absconds with the money. This movie wasn’t meant to be serious.

But even with all of its silliness, it’s still a decent poker movie and does a pretty good job of pointing out how tells can be a gambler’s downfall. With that said, Maverick is meant to be enjoyed, not imitated for learning poker strategy.

Conclusion

Gambling is a popular subject for the folks in Hollywood. In addition to the seven movies above, there are plenty of other films like The Gambler, Runner Runner, The Cincinnati Kid, the original Ocean’s 11, The Hustler, and Let it Ride. Heck, even Rain Man and The Hangover feature gambling.

In all of these files, screenwriters and directors combine scenes of people playing slots, poker, or betting on sports with action, heists, drama, and even history. All of these seven movies, each in their own way, showcase Hollywood’s take on movie-making mixed with gambling. In the end, all of these movies are entertaining to watch, and some are truer to life than others.

We suggest you watch them all for their own merits. Just stick to Rounders if you want true-to-life and Maverick if you need a good laugh.