Movies have captured the imagination of billions around the world with their ability to either show us things we couldn’t have imagined, or the opposite, present ordinary, everyday activities in a new and exciting light. One of those regular activities we’re all familiar with is gambling. In real life, playing roulette or blackjack is hardly a glamorous affair – most of us tend to play live casino on our phones in bed or while waiting for the bus, and even when in physical casino most of us don’t casually sip on a shaken-not-stirred martini while revealing a straight flush at the poker table. But movie characters can not only make gambling look very cool, but also frame it within a narrative in which it’s life or death – sometimes literally!

Today, we’ve decided to honor these high-stakes cinematic gambles with our very own top 10 list! Before we start, however, it’s important to set some ground rules. First of all, in order to classify as a “casino movie” in our book, the film must be intricately and inseparably tied to casinos or poker. Unfortunately for “The Hangover”, just having one really iconic and meme-able gambling scene doesn’t count! Of course, movies that feature gambling or make it a central plot point have priority, but we’ve also included movies that only focus on the inner-workings of casinos without any of the main characters gambling. Last, but not least, these movies are not ranked on their objective quality as movies, but rather on how well they represent the details of casinos and gambling (“well” in this case not necessarily meaning realistic, just entertaining and interesting).

Without further ado, let’s get right into the list!

10. Bugsy (1991)

The real life story of Bugsy Siegel (the man often credited with turning Las Vegas into the casino haven it is today) is fascinating, and absolutely worthy of a movie adaptation. We’re talking about an assassin who rose through the ranks of the mob, becoming a mafioso superstar before deciding to go straight with a legitimate casino, only to die after succumbing once more to his dark impulses. You couldn’t ask for a better story! Unfortunately, this wasn’t what director Barry Levinson wanted to make a movie about. He wanted a love story.

The movie sadly skips over most of Bugsy’s life, starting in 1941 – way after he had built his infamous reputation in both New York and Hollywood. Not even the creation of the Flamingo, Vegas’ first major casino resort, is focused on much. Instead, the core theme of the movie falls squarely on Bugsy’s passionate affair with Virginia Hill, a fellow mobster who stole his heart even though he was already married.

  • As such, “Bugsy” becomes less “The Sopranos” and more of a dark, criminal romance.

Of course, that isn’t necessarily a bad thing. Critics and fans alike enjoyed the movie when it came out, and its unique visual style earned it two Academy Awards. We’re not saying it’s a bad movie, by any means. We’re just bummed out that the focus was not on what we consider to be the most interesting part of Bugsy’s life. But who knows, maybe one day we’ll see a phenomenal Netflix crime series or a 3 hour long Scorsese movie about him which does the full legend of the wicked mobster justice!

9. Ocean’s Eleven (2001)

The movie which made heist films cool again! Just after being released from prison, professional thief Danny Ocean (George Clooney) decides that the only lesson he’s learned in the slammer is “go bigger” – which we bet many gamblers can relate to. He reveals he’s hatched a plan to rob three of the biggest casinos in Las Vegas in the same night, making off with a grand prize of $150m in cash. To achieve his goal, he connects with ten of his former associates, each specializing in a different field and, of course, each played by an A-list actor. Brad Pitt, Matt Damon, Casey Affleck, Don Cheadle and many more join Clooney in an unprecedented A-list cast, especially for 2001!

You might be asking yourself “Hey, if the movie is so good, why is it only at #9?” That’s because, unfortunately, gambling isn’t much of a focus of the movie. Which makes perfect sense, it wouldn’t be a great look if Danny and his Eleven put the heist on hold to play a few hands of blackjack, right?

  • What does make the movie special, however, is the attention to detail when it comes to the world of gambling.

Ocean is robbing three very real casinos (the Bellagio, the Mirage and the MGM Grand), and while obviously the method he concocts to rob them wouldn’t work in reality, the Nevada gambling regulations they refer to are very real, as are the many of the little details added to the movie to bring Vegas to life. For example, Brad Pitt’s character Rusty is introduced teaching some actors how to play poker, which is actually a genuine occupation for professional poker players in Vegas. They don’t make all their money off of winning pots, after all!

Basically, despite the fact that casino games aren’t an essential part of the movie, “Ocean’s Eleven” is a blast whether you’re a gambler or not!

8. Maverick (1994)

Not all casino movies need to be entirely about gambling – sometimes, getting to the casino is half of the fun! Set in the Old West, Maverick (based on the TV show of the same name) tells the story of Bret Maverick (Mel Gibson), who’s a few thousand dollars short of the entry fee to participate in a major poker tournament. He’s got the skills to win it, but that doesn’t mean much when he can’t even get a seat at the table, right? Thus begins his quest, alongside gamblers Bransford (Jodie Foster) and Cooper (James Garner) to scam his way into the remainder of the funds before finally winning the tournament! What could possibly go wrong, right? As it turns out, literally everything.

  • Maverick is the rare kind of casino movie that doesn’t take itself very seriously.

Instead of focusing on the “depravity” of gambling and on the moral bankruptcy of gamblers, it revels in it. Maverick and his companions are objectively bad people who are more than happy to lie, steal, cheat and scam, all in the goal of making off with the $500,000 prize money. They’re not above tricking others or each other, often repeatedly, in order to gain even the smallest advantage in their struggle. Poker is, at the end of the day, a game about bluffing and outsmarting your opponents even in the face of bad luck, and so it’s not hard to believe that the main characters are good at it, given all the schemes they pull before a single card has been dealt at the tournament.

If you’re tired of dark, cynical takes on casino games and are in the mood for watching a few con artists desperately cheat to come out on top while their plans go wrong at every step, then Maverick is going to be your cup of tea!

7. Molly’s Game (2017)

The newest film on our list, and also one of the most recognized by critics and awards ceremonies, scoring five accolades and an additional 19 nominations, most of them for its writing and direction by the legendary Aaron Sorkin (an actor and writer who made this film his impressive directorial debut). Based on the memoir of Molly Bloom (played in the film by Jessica Chastain), the movie tells the story of how she went from an injured athlete into a poker mogul who ran several underground poker tables for the rich and famous – including the mysterious Player X (Michael Cera), a sociopathic Hollywood celebrity who is allegedly based on Spider-Man actor Tobey Maguire.

The movie doesn’t focus too much on the actual game of poker, which is why it’s ranked so low despite being a genuinely entertaining ride that sticks surprisingly close to facts (if embellishing them a bit for dramatic effect).

  • There aren’t many intense high-stakes poker showdowns to be had there, but that’s not really what the movie is about.

The focus is on the organizer, the dealer, not the players – and, quite frankly, it’s a side of the poker world that is barely, if ever, explored. Still, we need to stick to our established rules and guidelines. Perhaps if Molly had cracked her knuckles and taken on Player X in a one on one poker fight at the climax of the movie we would’ve ranked it near the top!

All joking aside, Molly’s Game remains a fantastic look at the seedier side of the gambling world, away from the flashy lights and neon signs of Las Vegas, and is an entertaining ride from start to finish.

6. 21 (2008)

Too many movies on our list have focused on poker tournaments, and while we’re not quite done with them yet, we decided to take a breather and focus on a different game for a change – blackjack, one of our favourites, and the only casino game where being good at math is more important than being lucky! That’s the core principle behind 21, a dramatization of the real story of a group of MIT students who, between 1979 and 2000, managed to win hundreds of thousands of dollars from various casinos around the world. Of course, the movie makes no attempt to portray these events factually, and instead uses a made up cast of characters that go through vaguely similar adventures over the course of a few months.

Look, we’re not saying 21 is perfect. We would’ve liked to see the true story of the MIT students being done justice, and we certainly would’ve liked to see them portrayed accurately (the actual team consisted mostly of Asian-Americans, while the cast of 21 is mostly comprised of white actors).

  • With all that said though, the movie ranks so high on our list because it is the very definition of a guilty pleasure.

It’s just so over the top and dramatic that there’s no way you won’t be entertained by its high-stakes blackjack games. Most importantly, it’s a movie that unapologetically makes math and card counting cool – and honestly, we’re all for that.

Is it a good movie? That depends on who you ask. But if you ask us, you’ll never be bored watching 21!

5. The Cincinnati Kid (1965)

It’s truly hard to resist a good poker tournament, isn’t it? Unlike Maverick, however, The Cincinnati Kid dedicates almost the entirety of its runtime to that tournament, with only a minimal amount of setup and distractions. The focus is right where it should be: on the cards, and on the people holding and dealing them. Our main character, the Kid (Steve McQueen) is an up-and-coming poker prodigy who seeks to take down and humiliate Lancey Howard (Edward G. Robinson), a world-famous poker player that’s visiting his town. While the first act is focused on establishing the Kid and Howard, as well as the people around them, like the Kid’s friend and dealer Shooter (Karl Malden), the majority of the movie is focused on the tournament as each of the six opponents fall down one by one, until it’s just the Kid versus Howard. Will the young prodigy succeed and make a name for himself, or will his inexperience in the face of a seasoned veteran prove to be his undoing?

  • While you may not have seen “The Cincinnati Kid”, you’ve almost certainly heard the name or seen a reference to it.

“Cincinnati Kid” has become something of a slang term in certain circles for an up-and-comer, especially in poker. Several contemporary movies and TV shows also parodied the intense poker scenes, such as the episode of “The Brady Bunch” titled “The Cincinnati Kids”. Its influence continues to the modern day, with the movie serving as inspiration for one of the storylines in Sin City: A Dame to Kill For (2014) which depicted a young poker player going up against the unscrupulous businessman Howard Roark.

Not only does “The Cincinnati Kid” still hold up as a tense movie for casual fans and poker players alike, but its influence on pop culture is unmistakable and still going strong decades later. How many other moves can say the same?

4. Casablanca (1942)

Certainly the oldest movie on our list, and a good candidate for the world’s first casino movie! Not only that, but it also deserves credit for using the casino as a thematic element central to its narrative, the game of roulette serving to accentuate the movie’s themes about the impossibility of true neutrality. American expat Rick Blaine (Humphrey Bogart) owns said casino/bar in Casablanca, Morocco – a place that attracts a varied clientele appropriate for the height of WWII. French and German officials, as well as refugees hoping to make their way out of occupied territories and into the US. Of course, the story truly begins when one particular client, the wife of a Czech Resistance leader and Rick’s first love, enters the casino to ask for a favor.

Rick professes true neutrality – he wants no part to play in the war, and claims to treat all of his guests equally regardless of which side they’re on.

  • This neutrality is represented by the game of roulette that is often played at his casino, a game that has an equal chance of making any number of the wheel a winner.

However, when a Bulgarian couple seeking money for papers to flee to the US approaches Rick, we learn that his roulette isn’t quite as neutral as he claims, and (in a now-iconic scene) Rick subtly manipulates the croupier to ensure the couple win enough money to buy their papers. Just like his roulette table, Rick himself isn’t nearly as neutral as he claims, and he ends the movie choosing to return to the US to fight in the war.

By modern standards, Casablanca may almost seem primitive, and its themes aren’t exactly what one might call “subtle”. However, it’s worth noting that this movie came out almost 80 years ago, and the only reason it seems primitive to us is because literally thousands of other movies have built upon the blueprint it established. And that’s no small feat!

3. Croupier (1998)

We’re fans of high-stakes poker hands and ingenious plans to beat the casino just as much as anyone else, but what really gets us going – both as gamblers and movie fans – is when a movie is capable of utilizing the casino setting and its games as a narrative device to show us more about the protagonist’s state of mind without telling us. With that in mind, you shouldn’t be surprised that Casablanca ranked so high, or that Croupier ranked just above it!

The movie tells the story of a writer named Jack (Clive Owen), who, after struggling with writer’s block, decides to take on a job as a roulette croupier in a prestigious casino. Jack is good with numbers, winning him the favour of the casino’s manager and the attention of croupiers and gamblers alike. Jack quickly finds that he’s enjoying the job, but not in the way we enjoy writing about the best casino movies – instead, he takes pleasure in the struggles of ordinary people as they lose everything.

  • Just as the roulette odds are always leaning in favour of the casino and against the people Jack serves as croupier, so too does life seem to stack against the people closest to him.

And the more Jack remains at the roulette table, the more detached and emotionless he seems to get.

When talking about Maverick, we mentioned the existence of dark and cynical casino movies that can only look at gambling negatively. Croupier is one of those dark movies, but unlike most of its contemporaries, it does so exceptionally well. True, the movie probably won’t make you rush to the nearest roulette table after it’s over, but the movie makes it clear that, whether you do or don’t, the house always has the edge. And the croupier is just there to take the chips.

2. Casino (1995)

Remember back at the very beginning of the list, when we said that the story of Bugsy Siegel might be best told in a 3 hour long Scorsese movie? Well, Casino is the closest that we’re going to get, and while it tells a made up story, there are several parallels to Bugsy’s story which made us believe Scorsese was at least inspired by it for his own mafia casino tale. Sam (Al Pacino) is running a successful casino that’s a front for the mafia’s money laundering operations. He ends up falling for and marrying a hustler named Ginger (Sharon Stone), despite her dark past (a clear parallel to Bugsy’s marriage to Virginia Hill). A few years later, an investigation into the casino’s skimming and laundering operation quickly begins to spiral out of control, testing Sam’s resolve to both keep his casino and his family safe, and more importantly, close. But can he keep both? Can he keep either?

  • If you’ve ever seen a Scorsese movie, like Taxi Driver, Raging Bull, King of Comedy or Goodfellas, you know exactly what you’re in for with Casino – and we say that in the best possible way, as those are some very, very big shoes to fill.

Does Casino manage to top those movies? No, perhaps not… But it’s hard to hold that against it, we’re talking about some of the best crime movies of all time here. What it does do is stand right alongside them as one of Scorsese’s finest. It does what Scorsese does best: showing us a protagonist who wants more than he has, yet is unable to keep grasp of what he already has as he descends further and further into the criminal underworld. And, in this case, he also does it through the lens of a casino, which, as we’ve discussed before, is an extremely potent metaphor for these kinds of stories.

If you’re a fan of Scorsese, or hell, if you don’t know who he is, but like the idea of crime films, do yourself a favour and watch Casino. You won’t be disappointed! You have Casino.Online’s guarantee!

1. Casino Royale (2006)

How could this not be at the top of the list? Undoubtedly the best James Bond movie ever made, one of the greatest action flicks of the modern age and, of course, a film seeped in gambling and casino culture, as its name suggests! Daniel Craig made his debut as James Bond in a prequel story about Bond’s first assignment after getting 00 status. Said assignment pits him against a “terrorists’ banker” known as Le Chiffre (played masterfully by Mads Mikkelsen) in a high-stakes poker tournament. Should Le Chiffre win, he’ll be able to use the money to fund the activities of terrorist associations, meaning that it’s imperative for Bond to get in the game and score that big win.

At first glance, the concept of an action movie centered around a poker game sounds rather boring, and it’s hard to imagine how it could possibly live up to the glorious opening action scene in which Bond chases down a free-running bomb maker played by parkour legend Sebastien Foucan.

  • But “Casino Royale” masterfully weaves the tension of the poker game with Bond’s own activities as a spy.

In between hands, he must strike deals with covert CIA agents, gather information on Le Chiffre and his other opponents and survive multiple assassination attempts – it’s impossible to have the spy stuff without the gambling stuff, the two “sides” of the movie influence each other at every step. And that is, of course, without mentioning the love story between Bond and his handler Vesper, which shows us exactly how Bond turned into the infamous womanizer with a heart of stone from the past movies.

There’s no doubt about it – “Casino Royale” is a real masterpiece, a gem of casino movies and action films in general. Even if you’re not a fan of James Bond, this is one mission you don’t want to skip – especially if you’re a poker player!

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Jacob Evans Written by Jacob Evans