Our top 5 favourite gambling movies

May 29, 2023
A massive number of movies deal with gambling in some capacity. You’d be hard-pressed to find someone who hasn’t seen at least one movie that features gambling in some way shape or form.

A massive number of movies deal with gambling in some capacity. Be they gangster films, heist movies, or character studies, you’d be hard-pressed to find someone who hasn’t seen at least one movie that features gambling in some way shape or form. But some movies are better than others; so, this list covers 5 of our favourite gambling movies of all time.

Background: A History of Gambling in Films

Gambling is no longer the stigmatized pastime that it used to be. Perhaps we have digital entertainment to thank for this; nowadays, gambling games are far more accessible than they ever have been. We can access games like crypto roulette, poker, and blackjack, all from our phone or laptop.

Gambling is the subject of a great many films, too. Much of the public has long been fascinated by gambling, for better or for worse; attitudes towards the activity are more or less reflected by the wide array of movies that display it in both a positive and negative light.

5 of our favourite gambling movies

The list below covers 5 of our favourite gambling movies of all time. Gritty, realistic, and deeply compelling, all these films are well worth a watch, even if you’ve never stepped foot inside a casino before.

The Card Counter
Oscar Isaac stars in The Card Counter, a film about a man with a complex, chequered past. In the movie, we learn that Isaac’s character, William Tell, actually taught himself how to play cards while locked up in prison; indeed, Tell’s life turns out to be one defined by impermanence, instability, and chaos (somewhat ironically, given how Isaac himself has reflected on the role these themes play in his own professional and personal life).

Intense, dark, and dramatic, Isaac’s performance in the Card Counter has to be seen to be believed. While the film itself hasn’t quite reached the classic status that some of the other entries on this list has, we can still heartily recommend it to anyone who enjoys a strong, thrilling drama.

The Ocean’s Franchise
Probably best described as hybrids between gangster movies and gambling movies (as well as being among some of the best gangster movies of all time), the Ocean’s franchise sees a group of former Service men work with Spyros Acebos, a man with gang associations, to rob an assortment of casinos… and then end up needing to rob more casinos in the aftermath.

The Ocean’s franchise is also noteworthy for being a comedy; naturally, many films that manage gambling or gang activity tend to be on the darker side. By contrast, the Ocean’s movies are light-hearted and feature strong ensemble casts with fan-favourite actors like George Clooney, Matt Damon, and Brad Pitt.

The Gambler
The Gambler features Mark Wahlberg in a starring role as a professor with, shall we say, a fairly complicated life. Wahlberg’s character, Jim Bennett, is blatantly self-destructive, gambling his money away and borrowing massive amounts from a loan shark. Bennett also pursues a relationship with one of his students, clearly at odds with the standards of conduct and professionalism expected of him in his role as a professor.

As you can probably imagine, The Gambler quickly turns into an absolute roller coaster ride, with one turn after another. The ending is ultimately uplifting, though, and Bennett learns plenty of very valuable lessons along the way.

California Split
Regarded by many as one of the best gambling movies of all time, California Split is a bonafide classic. Dealing with themes like hedonism, freedom, the pressure of societal expectations, and the concept of living a good life, California Split sees two men, Bill and Charlie, pursuing that ever-elusive jackpot while seemingly being thwarted at every turn.

Ultimately, the two men are too different to continue gambling together in the way that they have, and they respectfully go their separate ways after a streak of some real success. Bill manages to escape from the grips of gambling addiction and returns home to continue with his life.

Overall, California Split is an uplifting and heart-warming tale of friendship and personal growth that is absolutely worth a watch.

Casino Royale
Starring David Niven as James Bond, the 1967 version of Casino Royale is, frankly, bonkers. It’s a totally absurdist look at the world of gambling as a whole, and David Niven does an excellent job in his portrayal of 007, and the soundtrack, visuals, and set design are all very entertaining, if a little (read: very) over the top.

While the 2006 remake of the film, featuring Daniel Craig as James Bond, was well-received, the original is, in our opinion, the more entertaining of the two. Despite Craig’s powerful performance, the bombastic, absurd presentation of the original makes it far more memorable, even if it lacks the cool, edgy appeal of the newer remake.

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