Best Gambling Movies of Last 25 Years

Every few years, gamblers and degenerates around the world unite over a new mainstream gambling themed movie release. While many of these movies end up playing to the masses and either distort the facts, ignore basic gambling principles, or both, some of them end up being absolute classics. If you are a gambler, you probably have seen most of the movies listed below. Some movies end up helping to launch worldwide trends (see Rounders and the poker boom) while others give insight into the early days of Las Vegas (Casino). From Robert De Niro to Matt Damon, these movies featured some of the biggest stars in all of show business.

There are many movies that date back to the 60s, 70s, and earlier that are also gambling classics, but this article focuses on the most modern of casino film. As the gaming industry advances each year, new casino movies with interesting plot twists will inevitably come to fruition. For now, this is our list of the best, most authentic and real gambling movies of the past few decades.

1) Casino

Casino MovieIt is hard to dispute that “Casino” is the number one gambling movie of all time, let alone the past 25 years. It is loaded with many of the most popular stars in entertainment history, including Robert De Niro, Joe Pesci, Sharon Stone and James Woods. Outside of the overflowing amount of talent in the film, “Casino” also presents one of the most interesting gambling plots available; Old School Las Vegas.

Instead of focusing on the old version of Vegas, known today as “Downtown” or “Fremont Street,” Casino instead highlights the beginning of what is now the modern day Strip area of Las Vegas Boulevard. Many visitors to Las Vegas do not realize just how shady the early years of the town were, and “Casino” does a good job of depicting just how dangerous and cutthroat the industry was.

The movie is unique because it gives insight into the view from both the player’s eyes and management’s eyes. Joe Pesci is repeatedly seen as both the gambler and the house, a dangerous habit that eventually catches up with him. Pesci turns from villain to victim as the movie progresses and the cast of characters vanishes, one at a time, as a result of the fast and dangerous lifestyle that they lived. Casino encompasses everything that is Las Vegas. Below is a short clip from the film that depicts the dangerous lifestyle associated with Las Vegas in the early days.

2) Rounders

roundersRounders is the undisputed number one poker themed movie of all time, and is clearly a top 5 gambling movie as well. Released in 1998, it helped to give legs to the poker boom that would take place in the early 2000’s. If you were new to poker, watching Rounders would both be informational and exciting, as it was partially educational and dramatic at the same time.

The two main characters in the movie did not hurt its popularity, as it featured Ed Norton and Matt Damon. There are just a few basic flaws in the movie, but they are very technical, and do not diminish its overall quality. One of the most intriguing dynamics of this movie is in its realism. It was filmed with realistic underground New York poker games and even in real life casinos, most notably the Taj Mahal in Atlantic City. The movie portrayed the real lifestyle of full time poker players of the 80’s and 90’s and its plot keeps audiences interested from the beginning to the end.

3) Owning Mahowny

owning-mahowny“Owning Mahowny” is in a category of its own among these top gambling movies as it exclusively focuses on the dark side of gambling, and in particular, gambling addiction. In an ironic twist and dose of reality, the main character was played by Philip Seymour Hoffman, who himself died tragically and unexpectedly in an illustration of the dark side of Hollywood itself.

This movie is also interesting because it depicts a true story. It takes place in the 1980’s, when Las Vegas and Atlantic City were the two gambling destinations of choice in the United States. Mahowny himself is from Canada and makes frequent, nerve racking trips to the US with significant amounts of cash. Eventually his gambling problem catches up to him, despite his ability to recoup all of his prior losses. In real life, Caesars Entertainment (specifically, Caesars Atlantic City) too had to pay a penalty for enabling Mahowny to fall into a downward gambling spiral.

4) Ocean’s 11

Ocean's 11 Movie“Ocean’s 11” does not emphasize the players or the casinos themselves, but instead those who seek to take advantage of them and their money. A team of professional thiefs and robbers assembles to take down the powerhouse casino in a very modern setting. While the movie stretches the realm of feasibility, its strong cast of characters and frequent plot twists keep viewers engaged.

The detractor from Ocean’s 11 is found in its follow up releases, Ocean’s 12 and Ocean’s 13, which did not live up to the bar set by Ocean’s 11 itself. Many viewers were quite disappointed in the quality of these sequels, but that is to be expected, as casinos being robbed over and over again will eventually become a tired and played out concept.

5) 21

“21” is the only blackjack themed movie in this list, but like “Owning Mahowny,” it is based on a true story. The movie tells the story of a team of blackjack card counters from MIT, one of the most prestigious universities in the world. Today, some of these card counters remain relevant, like Andy Bloch, who went on to become a well known poker player, most notably during the poker boom.

Kevin Spacey plays the role of team leader to perfection in “21,” and the movie illustrates just how risky and tedious the process of successful blackjack card counting is. The team experiences ups and downs throughout the movie, and while the money is coming in, it shows that being a professional blackjack player is not as easy as it may seem.