The best way to mentally prepare yourself for an upcoming trip to Las Vegas or your weekly game with the boys is watching a great gambling movie. Not only will it give you the basis for a perfect poker face and controling your emotions, it’ll get you excited for the feel of plush carpet beneath your feet, the slot machine lever in your palm, and the quiet thwack of playing cards snapping between your fingers. This is a top list for the 15 best gambling movies of all time. If you’ve already seen them you’ll agree with me, and if you haven’t then what are you waiting for? Start watching them right now and get yourself hyped up!
15. 21 (2008)
This movie has one of the most recognizable titles and most notorious gambling premises out of all the gambling movies on this list. Based very, very loosely on a true story, 21 follows the story of the MIT Blackjack Team, a group of students who developed a system to beating casinos at real money blackjack and won insane amounts of money over the span of many years. This team helped establish advantage play as a means of making a profit from casino games, and gives inspiration to those hoping to make a living off professional gambling.
Receiving a rating of 6.8 out of 10 on IMDb, this movie’s failings may have come from its hiring white actors to play a widely diverse team, or taking many artistic liberties to embellish the story. Regardless, this movie has helped establish a class of gambling movies made in the late 2000s. It’s worth a watch, at least so you can take part in a discussion on whether or not it does the true story justice.
14. Owning Mahowny (2003)
Another movie based on a true story, Owning Mahowny tells the story of a banker with access to deep pockets and casinos which enable his all-consuming gambling addiction. IMDb rewarded this film with 7.2 stars, taking into consideration Philip Seymour Hoffman’s convincing and sometimes heart-wrenching performance. Committing bank fraud in order to support his unhealthy need to gamble, Hoffman’s character, Mahowny, must reconcile his ways with the life he wants to live. And while the audience can’t help but root for him, they may also feel the urge to cheer on the detectives who are struggling to sort out one of Canada’s most notorious cases of bank fraud.
This movie isn’t about the glitz and glam of casinos, it’s about the practice of gambling and the toll it may take on unsuspecting victims. This movie has big hair, big glasses, and shoulder pads galore – enough to transport you back in time and experience the event as if you were really a part of it.
13. The Cincinnati Kid (1965)
Steve McQueen is known and loved for his rebellious, bad-boy persona and The Cincinnati Kid is no exception. Set during the depression, this movie has become a nostalgic nod to the past and pulls a ranking of 7.3 stars from IMDb. The Cincinnati Kid supersedes the category of gambling, becoming a part of the American film canon. McQueen plays none other than “the Kid”, and his character is a rambunctious young gambler looking to make a name for himself. He has to beat Edward G. Howard’s character, Lancey, the biggest name in poker, in order to establish himself. In this movie, the audience follows his dangerous journey to becoming the best, which takes its detours as the Kid navigates his way around tempting and beautiful women along with men who are out to get him. Watch this film, take in the impressive performance, wild gunshots, and gambling culture, and get the inspiration to get out there and make a name for yourself as a fearsome opponent.
12. Hard Eight (1996)
Also rated 7.3 out of 10 on IMDb, Hard Eight makes up a part of the arsenal of gambling movies made in the 90s. Starring big names like Philip Baker Hall, John C. Reilly, Gwyneth Paltrow, and Samuel L. Jackson, this star-studded movie doesn’t disappoint. It covers two sides of Vegas culture, with the shiny lights and endless money of the casinos, as well as the down and dirty side of prostitution, crime, and extortion. This film is dramatic and violent but also has a hilarious quality tacked on by the cluelessness of some characters. With Hard Eight, you feel the hope as Sydney picks up John from the slums and makes a proper gambler out of him, and then it all takes an interesting, sharp turn for the worse when a woman’s wiles are introduced into the mix. The movie is fun to watch, and you may even learn a thing or two from Sydney’s lesson on how to become a proper, moneymaking gambler.
11. The Gambler (1974)
The Gambler is the second movie on this list to touch upon the destructive qualities of a gambling addiction. Rated 7.3 stars on IMDb, this film tells the story of Axel Freed, a literature professor who loves to gamble. At first it is just a hobby but as time continues, he finds that he needs to borrow money from friends and family. Eventually he finds that his only option is to take out a loan from some very dangerous men. Throughout the film, you follow Freed as he tries to find the money needed to divert these men and save his own life in the process. For those looking to watch a film about gambling and not for the thrills and giggles of Vegas life, this is a great movie night option, though maybe not for a family viewing. It also serves as an ominous warning against the dangers of falling into an addictive pattern of gambling. Maybe it’s just the dose of realism you need before heading to a casino with your life savings in hand.
10. A Big Hand for the Little Lady (1966)
No movie list is complete without a salute to the Wild West. This classic style Western is all about high stakes, the luck of the draw, and retribution. Receiving 7.4 out of 10 stars on IMDb, this movie is perfect for someone looking for a mix of gambling and a battle of the wits. The story starts with the territory’s five richest men dropping everything and everyone to meet for their annual poker match. One of the players even left his daughter’s wedding for the game, so you know the stakes are going to be mighty high. Everything is going as it should be until an out-of-towner buys in. To know what raised stakes and deception follow, you’re going to have to watch the movie for yourself. Make a bowl of popcorn or a batch o’ baked beans, and press play.
9. Rounders (1998)
Rounders is a movie straight out of the late 90s, with a brilliant, young Matt Damon at the forefront. His character, Mike McDermott, has to reconcile the responsibilities of day-to-day life and his lifelong dream of playing in the Poker World Series. He attends law school, has a cute girlfriend, and plays poker on the side until a round of Texas Hold’em goes horribly awry. He tries to stay on a straight path until his friend, played by Edward Norton, gets out of Jail. He returns to the world of poker to save their lives, playing risky games with high stakes – a real life or death situation. The film culminates with an all-or-nothing match, and everything is on the line. This movie is a great pick for realistic games and table banter. If poker is your game, then this may just be the perfect movie to play to your tastes. Check out our recommended Top 7 Best Poker Movies Ever.
8. Fear and Loathing in Las Vegas (1998)
Based on Hunter S. Thompson’s novel of the same name, this 7.7 star-rated movie has become a staple in the diet of American film. About more than just the gambling side of Sin City, Fear and Loathing in Las Vegas is about the culture that attracts so many people to the infamous city. Riding passenger seat on the psychedelic journey of Duke (Johnny Depp) and Gonzo (Benicio del Toro), you feel the first person film technique take effect as they attempt to subdue the drug-induced monsters in their heads with even more unpronounceable substances. Both confusing and hilarious, this film will take you on a trip as you try to figure out what just happened and what kind of crazy antics these colorful characters are going to get themselves into next. Over the years, this film has become a cult classic, and unless you want to feel like you’re missing out on all the inside jokes during your next Vegas visit, I highly suggest you give this movie a watch.
7. The Hangover (2009)
One of the highest grossing films about gambling, The Hangover has everything from babies to mobsters to a tiger belonging to Mike Tyson. Receiving 7.8 out of 10 stars on IMDb, this movie tells the story of three unlikely friends who are trying to piece together the hazy details of the night before in order to find their fourth friend. Their deadline grows increasingly shorter as the missing friend’s wedding approaches. The Hangover is a raunchy, gut-busting comedy that can lighten the mood of any room. My only suggestion is to make sure you give it a good look through before sitting down and watching it with the kids. It’s definitely a great way to mentally prepare yourself for what you might go through after a bender in Las Vegas. If there’s one lesson to be learned from this movie, it’s always know what’s going in your drinks – also, don’t mess with Mike Tyson’s tiger.
6. Ocean’s Eleven (2001)
If there’s one movie about gambling that everyone will know about, it’s Ocean’s Eleven. Rated 7.8 on IMDb, this movie tells the tale of a complex heist being planned and performed. George Clooney plays the lead, going after world-famous Las Vegas casinos such as the Bellagio and MGM Grand. Other performances by Brad Pitt, Matt Damon, and Julia Roberts make this an impressively star-studded cast and their performances don’t leave you wanting. Showing the precarious underbelly of casino security, the audience of this film will hold their breath and subsequently feel the excitement stirring as each phase of the plan is being executed. There is also something to be said for the fact that this movie can portray a heist without too much guts and gore. It’s a great family flick for those who have a long enough attention span. And the best part about this movie is that you never know what will come next – if you haven’t seen it yet you’re missing out!
5. The Hustler (1961)
This movie launched Paul Newman’s acting career, and for good reason. The Hustler received an 8 out of 10 stars on IMDb, which is no easy feat in the world of movie ratings. A film adaptation of Walter Tevis’s novel of the same name, the drama unfolds to reveal a small-time pool hustler hoping to make it big. Paul Newman, who plays the lead character, “Fast Eddie”, has a hot temper and a lot of pride. He has to prove himself against all odds, and keep his loved ones safe in the process. This movie leaves the casino behind, taking place in other betting establishments such as pool halls and derbies. If you’re looking to watch a movie about the excitement and risk of gambling but don’t want to keep up with the complicated strategies, then you’ve found the one. All there is to do now is press play, sit back, and relax.
4. Casino Royale (2006)
Another box-office hit, this movie is a staple in the James Bond franchise. Being the first 007 feature with Daniel Craig as the beloved figure of Bond, the audience is treated to a more vulnerable portrayal of Bond’s character. The setting takes place all over the world, showcasing gorgeous places like the Czech Republic, the Bahamas, Venice, and Montenegro. This Bond movie makes it as one of the top 5 gambling movies because the pivotal point of the movie hinges on a game of Texas Hold’em. If you’ve ever found yourself sweating out a tough match, you will definitely enjoy watching Bond, James Bond, keeping it cool in spite of every curveball his enemies throw his way. A fun action movie to watch with a little romance sprinkled in along the way, Casino Royale is a movie that you can bet will be well received at any viewing party. Make sure to grab a snack and make a tasty cocktail – and what goes better with a James Bond movie than a martini, shaken, not stirred. Casino Royale is one of the coolest films about casinos and gambling ever.
3. Lock, Stock and Two Smoking Barrels (1998)
Guy Ritchie has such a distinct directing style, and you would be able to recognize that it’s one of his masterpieces in a second. Lock, Stock, and Two Smoking Barrels is no different, featuring violent and bloody high-octane action, characters who are all colorful to say the least, and a circular plot that moves so fast it’ll make your head spin. Rated 8.2 on the IMDb scale, this is one of the best movies to watch when preparing for a fast-paced gambling environment. Set in England, this movie is about four friends who lose half a million quid in a game of three-card brag (it’s British, look it up). In the Ritchie tradition, these unlucky boys are at the mercy of a crime boss and have to find a way to pay their dues. Their medicine of choice: pulling off a huge heist. This fast-paced movie will keep you confused, excited, and laughing because of the idiotic characters. At the very least, it’ll make you think twice before betting money you don’t have.
2. Casino (1995)
This movie comes in at an 8.2 on the IMDb rating scale and it has definitely carved out its own place in the class of movies about gambling. If you’re feeling nostalgic about the roots of Las Vegas, then this movie has it all: casinos, the mafia, and actors Robert De Niro and Joe Pesci at the height of their careers. With lots of action, high stakes, and guns blazing, this movie will tickle your gambling fancy. Robert De Niro is right at home in his role as the owner of a casino, dealing with the destructive aftermath of an enforcer’s unpredictability. Joe Pesci fits this character like a glove, with the outcome of a classic gambling movie. It will make you laugh, cry, and bite your nails all the way down, but no matter what I promise that you won’t be able to stop watching until the very end.
1. The Sting (1973)
Rated the highest with an 8.3 out of 10 stars on IMDb, The Sting is an all-time favorite gambling movie. This film features Paul Newman and Robert Redford, who are two of the most attractive men in all of history. The film takes you on the journey of a young hustler who finds a partner in one of the biggest and baddest con men in the industry. To get revenge for done deeds, they need to beat a corrupt banker at his own game. You guessed right, the game is gambling! As the story unfolds, the con they’re trying to pull over the bad banker gets more intense and increasingly complicated, but Newman and Redford keep cool and are their famously suave selves. Hats off to the director of this film because this thriller will keep you on the edge of your seat the entire time.
