The Top 5 Greatest Gambling Movies of All Time

Words Top Five Next to Movie Reel With a Poker Themed Background Pattern

When it comes to films about gambling, there are almost too many to name. A lot of them are considered critically-acclaimed classics and are personally some of my favorite films.

Ranging from casino gambling, counting cards, and hustling, this particular genre covers a pretty broad range. If you grew up in Texas on a ranch and were raised by cowboys, it’s pretty inevitable that you’ll be sat down at the dinner table and taught the basics of poker at the very least.

Some of these films you might love or hate, but I’m going to list some of my personal favorites. In my opinion, here are the top five best gambling films of all time.

5 – Casino Royale (2006)

Some of you probably know who James Bond is thanks to owning a Nintendo 64 and wasting away every available hour playing GoldenEye.

My mom had to take mine away eventually because I wouldn’t put down the controller. I fell in love with James Bond, and at the time, Pierce Brosnan was the face of the license-to-kill 00 agent.

His movies were not my favorite, but I can thank him for at least planting the seed of interest in the whole 007 franchise.

Casino Royale is unlike any Bond film I had ever seen. Critics would go on to say that this was “the nearly perfect James Bond movie.”

The plot is great. Daniel Craig plays James Bond, and after receiving a license to kill, British Secret Service agent James Bond heads to Madagascar, where he learns about Le Chiffre, a man who finances terrorist organizations.

After find out that Le Chiffre plans to raise money in a high-stakes poker game, MI6 sends Bond to play against him, gambling that their newest “00” operative will destroy the entirety of this man’s organization.

The game is held at Casino Royale, Montenegro, and watching will definitely keep you on the edge of your seat. This is a film worth checking out if you haven’t seen it. It captures the essence of gambling by contrasting it with the dangers of how these men often gamble with their lives.

4 – Rounders (1998)

This film caught my attention due to the star-studded cast, including Matt Damon, John Malkovich, and Edward Norton.

The plot is fairly straight forward. There’s an underground high-stakes poker world that draws in the main characters with its potential for big money. What people are willing to put on the line—the cheating, the obsession with winning back what was lost, the lengths people are willing to go to in order to do that—is what makes this film stand out.

Rounders, I think, does a fantastic job at capturing this whole scene. John Dahl directed this exploration of New York private clubs devoted to high-stakes poker, with first-person narration from the film’s main character—law student Mike McDermott (Matt Damon).

Mike loses his entire savings of $30,000 to Russian club owner Teddy KGB (John Malkovich) in a hand of Texas holdem. Mike then turns away from cards, promising his girlfriend Jo that he will put all of his focus and attention toward his law school studies and their relationship.

Jo becomes concerned after Mike’s friend and former gambling buddy Worm (Edward Norton) is released from prison. It isn’t long at all before Worm lures Mike back into the poker rooms. Jo moves out, and Mike begins to lose interest in his studies and falls back into what he promised he would stay away from.

Worm has a huge prison debt, and a threatening character wants the money. Mike unfortunately falls into the trap of getting involved in Worm’s debts. There’s a $15,000 debt and a five-day deadline, so we watch Worm and Mike spiral into a sleepless, nonstop gambling binge.

It all ends with a confrontation with Teddy KGB (Malkovich), and for spoiler alert avoidance, I won’t go into how that all plays out. It’s definitely a flick I enjoy watching, and if you haven’t seen it, it’s well worth checking out.

3 – The Gambler (1974)

Here’s one my granddad showed me when I was pretty young. James Caan stares in this film, which they tried to remake in 2014 starring Mark Wahlberg. But as most remakes go, it wasn’t as good as the original.

In this film, we see Caan playing Axel Fred, a New York City English professor. Fred has a wealthy grandfather, a gorgeous girlfriend played by Lauren Hutton, and a loving mother who is a doctor.

From the outside looking in, it seems like Fred has it all. He has the perfect girl, he’s young, attractive, intelligent, and the world is at his feet.

Screenshot From the Movie The Gambler (1974)

The issue is that Axel Fred has a huge gambling problem. We see his life rapidly spiral out of control, consequence after consequence. As with most people that struggle with addiction, even in the face of losing things and putting his entire life in jeopardy, Fred still can’t stop gambling.

Because of debt, he borrows money from his mother, only to lose it all gambling. He’s obsessed with losing, with feeling risk, with placing himself in danger.

I appreciate the honest portrayal of this aspect of gambling. So many movies paint this positive picture around the casino-going lifestyle, so it’s refreshing to have a more honest portrayal. The acting is also superb.

2 – 21 (2008)

I really loved this movie, which is why it made it to the #2 spot on my short list here.

You see the same pattern that you see in a lot of gambling movies. A character is in debt, needs to pay bills, medical expenses, or whatever, and they resort to some form of gambling.

That’s the case here, where we see Ben Campbell, a young and highly intelligent MIT student in Boston who’s chasing the American dream. Coming from a poor working-class background, Ben wants a scholarship to transfer to Harvard school of Medicine in hopes to become a doctor.

He quickly learns that he cannot afford the $300,000 necessary for the  four years of schooling.

One night, Ben is introduced by his unorthodox math professor Micky Rosa into a small and secretive club consisting of five other students. They are being trained by the professor to count cards in hopes of conquering the blackjack tables.

Intrigued by the idea of making quick and easy cash, Ben joins the club and embarks on weekend trips to Las Vegas. Using secret codes and hand signals, Ben is able to make hundreds of thousands of dollars, winning hand after hand at casino after casino.

Ben initially just wants to make enough to be able to pay his tuition, but as it goes with most, he quickly becomes addicted to winning. We see him progressively become corrupted by greed.

He puts his professor, as well as the rest of the group, at great risk when they all become a target for a brutal casino security enforcer by the name of Cole Williams. Williams has a personal vendetta toward their professor, so we watch a series of events undo everything the group has learned and earned.

This movie didn’t get the best reviews by critics, but I don’t care. I loved the film, and maybe it doesn’t deserve the #2 spot on the list, but that’s where I’m gonna leave it. If you haven’t seen it, the film is loosely inspired by the real-life MIT Blackjack Team. Watch and enjoy!

1 – Casino (1995)

This is not only the greatest gambling movie of all time, but this is easily in my top five for favorite movies of any genre across the board.

I fell in love with the Joe Pesci and Robert De Niro dynamic after seeing Goodfellas, but this movie was even better in my opinion. There are so many things that could be said about this film. Directed by Martin Scorsese, this movie is violent, vulgar, but absolutely beautiful all at the same time.

It does a masterful job of portraying the former corrupt workings of Las Vegas casinos. Taking place in 1975, we see the bookie and expert handicapper Sam Rothstein, known as “Ace” to his friends, going legitimate when the Chicago-based Italian Mafia hires him to operate the Tangiers Casino on the Las Vegas Strip.

Despite Sam’s past, he applies for the gaming license, and we watch his ever-changing title become anything but operator of the casino. In amidst of all of the violent chaos, the license is lost. Sam’s best friend from childhood, Nicky Santoro, wants to join the ride and is hired by the Mafia to basically be Sam’s bodyguard.

Screenshot From the Movie Casino

Profits are made in the casino while profits are skimmed off the top by Mafia bosses. Ace has a massive headache throughout the whole movie having to deal with Nicky, who has his own agenda, wanting to become the head mob boss of Las Vegas.

Nicky is reckless, careless, vulgar, violent, and puts everything Sam has in jeopardy. In the film, we see Sam marry Ginger McKenna, a person he knew from the get-go was a hustler and an addict. He’s in denial about her throughout most of the film, always giving her the benefit of the doubt at his own expense.

I won’t go into any spoilers on this one, but this film is an epic worth seeing. Witness what happens when goodfellas from the mean streets meet their wildest dreams of achieving, wealth, power, and everything else that comes along with the lifestyle of the rich and famous.

Conclusion

That’s my list! While these gambling films tend to span from different types of games, I can guarantee that there’s plenty of casino action to witness and enjoy.

Are there any movies you think I left out that should be included here? Let me know in the comments!