29 Best Gambling Movies to Watch Before You Die (Updated)

Tearing yourself away from the Casino can be tough, especially if you're on a hot streak, but you'd do well to enjoy some leisure time every now and then to recharge the batteries.

And there’s no better way to spend your leisure time than watching gambling movies about your favourite real money games.

Don’t know where to start? No worries.

Here is a list of 29 of the best gambling movies to keep your mind while you count your winnings.

29. Molly’s Game (2017)

Molly’s Game is one of the most recent gambling movies on our list, and it's a great crime drama to boot.

It is based on an autobiographical book called Molly's Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World!

The film tells the story of Molly, who runs two underground poker games attended by celebrities and criminals alike.

However, her life takes a sharp turn when the FBI discovers her gambling secret.

The story may have started as a book, but it became one of the most successful gambling movies of the decade. And it's all based around one of the most popular card games of all: poker.

28. Casino (1995)

Rated R for sex, drugs, and violence, this gambling movie with Robert De Niro and Sharon Stone will show you the truth behind the glitz and glam of a Las Vegas Casino.

27. Mississippi Grind (2015)

Before he starred in Deadpool, Ryan Reynolds took part in another blockbuster, Mississippi Grind.

The road film is about two gamblers: Gerry, who loves poker but doesn’t have much luck with it, and Curtis, who seemingly brings luck to Gerry. Together, they travel to New Orleans in hopes for a life-changing win against the best poker players in The Big Easy.

26. Gambling (2004)

If you’re looking for something serious to watch, well, Gambling might be the right film for you.

It’s a real emotional roller coaster of a story with a sprinkle of high-stakes gambling.

25. The Gambler (2014)

Mark Wahlberg stars in this remake of the 1974 classic film.

This gambling film tells a story about a literature professor with a simple outlook on life: you either have everything or nothing at all, a philosophy that he takes with him to the casinos.

Unfortunately, his gambling addiction leads to a massive debt to the owner of an underground gambling ring, as well as a notorious loan shark.

Fed up with his excuses, the gambling ring owner gives him a week to pay off his debt with cash - or his life. Desperate to keep living, the professor enlists the services of a few of his students to help him find the money.

Maybe they'll get extra credits.

24. Casino Royale (2006)

James Bond, the world’s most famous secret agent, has just gotten his status as a 007 agent.

His first mission for MI:6 has James Bond taking on a weapon dealer in a high-stakes match of Casino Royale.

In Casino Royale, there's more than just money on the table. But then, it's a James Bond movie, after all.

23. Lock, Stock and Two Smoking Barrels (1998)

From one of Britain's favourite directors, Guy Ritchie, this was one of the best gambling movies in the history of British film.

Set in England, an overly-confident card player enlists three of his best friends to aid him in pulling off a heist in order to pay off a gambling debt that he owes to a crime boss after he loses £500,000 in a fixed game of three-card brag.

Lessons learnt from this movie: 1. Don't gamble with crooks. 2. It is possible to have an English accent that doesn't sound like English.

22. The Cincinnati Kid (1965)

We all love a classic - and this gambling movie is a good one.

Steve McQueen stars in this all-American drama set during the Great Depression. He sets out to prove to other poker players that he is the best the world has ever seen.

Of course, to be the best poker player, you have to beat the best players, so he challenges veteran Lancey 'The Man' Howard in an attempt to take the title.

21. Owning Mahowny (2003)

What would you do if you had access to a multi-million dollar account and a love for high-stakes gambling?

Bet it all, of course.

You'll win it back eventually, right? If not, at least you'll have a reputation for being involved in one of Canada's most infamous bank-fraud cases. People will make movies about you.

20. 21 (2008)

Wouldn’t it be nice to win every time you play? Especially in the casinos of Vegas. And why not with one of the most popular card games of all? Blackjack!

21 is about a group of MIT college students, who form a blackjack team led by their professor. They use a card counting system that helps them fleece multiple Vegas casinos in order to win big and pay off their tuition fees. However, things go pear-shaped when the Vegas Casinos catch on to their scam. One of the best gambling movies in modern film.

What will happen now?

19. Let It Ride (1989)

Let's go bet on a few ponies!

In this gambling comedy, a cab driver hears a rumour about a horse that cannot lose - and wins big. Lured in by the easy money, he catches a gambling addiction.

18. Two for the Money (2005)

If you’re a football star, an injury can end your career in seconds.

That’s what happens to Brandon Lang.

Luckily, he keeps on working in the industry. His knowledge of the game and skill for choosing winners earns him the attention of one of sports betting's most prolific consultants who takes him under his wing.

17. California Split (1974)

Bill Denny is a casual gambler who meets Charlie Walters at a gambling club.

Impressed by Charlie's life as career gambler, Bill gambles more and more, getting into debt with his loan shark and eventually pawning everything he owns in order to take a trip to Reno for a high-stakes poker game and chase his dream of winning big.

16. Hard Eight (1996)

Sydney is a veteran gambler who feels most at home at casinos.

Towards the end of his life, he meets a younger man who is broke and has no luck at all. Sydney sees an opportunity to leave a legacy and takes John under his wing, teaching him all there is to know about the gambling business.

15. The Hustler (1961)

The Hustler will soon celebrate its 60th anniversary.

This was the movie that rocketed Paul Newman to stardom as he played an ambitious pool shark named Fast Eddie Felson. In his quest to be the best pool player to have ever lived, he goes under the tutelage of Brett Newman, who teaches him how to beat the best players and make a big time.

14. Ocean's Eleven (2001)

The best movies always get remakes - and this one has a star-studded cast. Anything less would have been unacceptable.

Here, George Clooney plays Danny Ocean who is fresh out of prison and wants revenge on the casino owner who had him locked up in the first place. That’s why he gets a crew together and plans to rob three casinos in one night. But did the casino owner get his comeuppance?

Matt Damon, Brad Pitt, and Julia Roberts also starred in this film. Danny Ocean and his crew went on to appear in two more gambling movies in the series.

13. A Big Hand for the Little Lady (1966)

This one is all about gambling and high-stakes poker in the Wild West.

Five of the richest men in Laredo gather for their annual poker game. Nothing keeps these high-rollers from their game and one of them even postpones his daughter's wedding to make sure that he's sitting at the table. Think about that the next time life gets in the way of your love for gambling and poker.

12. The Cooler (2003)

We all know that one guy who has the worst luck when it comes to gambling. Such guys should do themselves a favour and stay away from the gambling tables.

However, in this movie, casinos found a use for them. Once in a while, they'll hire such a man and send him in the direction of a player who's taking the house for too much money and have his bad luck infect them. They call these guys 'the coolers'. But what happens when a casino's favourite cooler becomes a lucky charm?

11. Fear and Loathing in Las Vegas (1998)

If you're going to the gambling mecca known as Las Vegas, don't hold back. Fill your trunk with every intoxicant known to man, get your buddy to ride shotgun, let the top down, and take a long trip into the recesses of your own mind.

I'll always remember this movie for that scene where the two main characters are trying to get into the hotel lobby, legless on their ether high. Classic.

10. Lucky You (2007)

The ladies love a winner...as long as he's winning.

9. Croupier (1998)

If you love gambling but don't have the skill for it, you could get a job as a croupier. At the very least you would get to see others win - and live vicariously through them.

This was the story of Jack Manfred, played by Clive Owen, up until he realized that he was witnessing golden material that he could use for his book. Inspiration comes from everywhere.

8. Bookies (2003)

College life is tough. Three students find that their student loans can't afford them the life that they want to live, so they start a business as bookies. Their booming business soon attracts the attention of local authorities as well as rival bookies in the same territory.

7. Kenny Rogers as The Gambler (1980)

"Don't ever count your money while you're sitting at the table."

This is just one of the many lessons that Brady Hawkes passed on to a young up-and-comer about the game of cards.

6. All In: The Poker Movie (2011)

Americans have been using poker to chase the American Dream for decades.

This is the gambling movie for you if you want to know all about the history of poker including how politicians have fought against the right of adults to choose how they spend their time and money.

All In shows how a professional poker-playing community went on to become a nationally televised sport, endorsed and played by celebrities such a George Clooney and Matt Damon.

5. The Good Thief (2002)

Gambling and law-breaking are always going to be closely associated. Here’s why - when some gamblers are in the red, they resort to crime to stay afloat. It makes the clean players look bad, but at least it makes for good stories.

In The Good Thief, an ageing gambler aims to rob a casino but the odds are stacked against him, as someone has spilt the beans about his plans. They just don't make drama/thriller movies like this anymore.

4. Dinner Rush (2000)

Dinner Rush follows the story of a father-and-son duo who own an Italian restaurant and have vested interests in the gambling world.

On one eventful night, they are hosting a cop, rival bookmakers, and a demanding food critic. The plot thickens faster than soup as the night draws to a climactic end. One of the great crime thriller gambling movies.

3. Killing Them Softly (2012)

Killing Them Softly is a story about an amateur crook who is hired by a poker player to rob an illegitimate game hosted by Mafia bosses.

However, these bosses are men of pride who aren’t going to let this insult go unpunished.

2. Saint John of Las Vegas (2009)

If you have a problem with something, it may be wise to avoid it.

In Saint John of Las Vegas, Steve Buscemi stars in a story about a gambling addict who moves away from Las Vegas. However, when he finds himself falling into old patterns, he realizes that he can't keep running away from his problems.

1. Holy Rollers: The True Story of Card Counting Christians (2011)

And now for the last in our list of the best casino movies of all time.

Have you ever been in a casino and sat next to a pious-looking gentleman with his hands to the heavens, praying for a good hand? He may just be a Holy Roller, part of a blackjack team made up entirely of church-going Christians.

But how can they justify their love for high-stakes gambling under the strict rules of their faith? If you want to find out, this gambling movie is for you.

_{This article was first published in 2019.}

AUTHORGiovanni Angioni

BioPolitical scientist, and gambling expert, I have spent the most part of the last ten years writing about the casino and poker industry. As a professional journalist, I work with FOX News, La Repubblica, the Economist, Politico, and PokerNews. As a gambler, I won money pretty much anywhere in Europe. As a gambling editor, I'll help you do the same.