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Casino Watchlist – 10 Gambling-Themed Movies You Ought to Watch

By: Will ConningtonNovember 2, 2018

If you are a fan of casino games, then finding a good gambling movie is often the best recipe for a relaxing evening – and you might even learn a thing or two. The best gambling movies should offer us a balance between popcorn fun and some deeper insights into the real-life casino world. There is quite a choice out there, so picking the top 10 titles was not an easy task – without further ado, here are the best gambling movies we can offer you!

You would be surprised – or not! – by the number of well-known actors that are also avid casino fans. It is perfectly natural that many of them have graced the big screen taking part in gambling-related movies. You will see many familiar names, including Kevin Spacey, Matt Damon, Justin Timberlake, Daniel Craig, Will Ferrel, Andy Lau, Philip Hoffman, George Clooney, Robert Redford – well, the list goes on for quite a while.

1. Casino Royale – License to Make a Killing Win

You simply can’t have a top gambling movie list without including the James Bond classic. The decorum, the rush, the high-stake games… and the masterful performance of the one and only Daniel Craig, of course. Casino Royale has established itself as one of the most influential gambling movies in recent decades due to its sheer scope – even though the 1967 version still holds its own even to this day!

The blend of Agent 007 and the casino world is somehow too perfect. The James Bond franchise has always shown us the lavishness of high society, and the 2007 rendition has the necessary budget to give us quite the visual treat. James Bond taking on an international terrorist during a poker tournament – it’s simply a match made in heaven.

The Casino Royale gambling scene has become extremely popular – without walking into any spoilers, we are speaking about the final poker match for the evening. It has captured viewers’ attention because it does a lot of things right – and just the right things wrong. Experienced poker players might scoff at the simplified way that some of the moves are presented, but Casino Royale actually has a solid foundation of detailed research and real player feedback. Ultimately, this is another beginner-friendly introduction to the world of advanced poker.

2. 21 – The (in)Accurate Portrayal of the MIT Blackjack Team

Kevin Spacey’s role as Micky Rosa, a professor from the Massachusetts Institute of Technology running his own blackjack team, was not one of his most memorable performances. However, the movie gathered huge attention in the gambling community as it brought attention to the phenomenon of the MIT Blackjack team on which it was based. The organised card-counting team which terrorised casinos in Las Vegas with their (borderline) legal advantage play during the 80s and 90s has left a significant mark in casino history.

21 is not a completely faithful adaption of the reality of the MIT blackjack team, which was rather more business-orientated and mundane. It does offer a fascinating glimpse into the system of counting cards which allowed the eager math students to make a reality of every casino player’s dream – gaining an edge over the House! That’s right – even though card-shuffling machines have restored the assertion that the House Always Wins, for more than a decade, the best card players actually managed to turn statistics on their head made a steady profit out of blackjack.

You will get your share of thrills and chills with 21, since the adaptation has emphasised the adventure aspects of the whole venture, and even added some romance to the mix. This is the only Kevin Spacey gambling movie you will find, even though in reality there was no actual involvement of professors in the MIT team – so he shouldn’t really be in it at all!

3. The Sting – It Has Aged Well

One of the timeless classics that fans of gambling movies tend to go back to. Much like Ocean’s Eleven, this is more of a heist movie, but it tackles heavily with sports betting and the gritty reality of organised crime during the 1930s. Don’t go away – the movie itself was produced in 1973, so it is not that retro.

Robert Redford takes center stage in this gambling movie as Johnny Hooker, an experienced Illinois grifter (which means a type of con-artist). His partner in crime is Henry Gondorff, portrayed by none other than Paul Newman. The iconic duo takes on the crime boss Doyle Lonnegan (Robert Shaw), choosing horse-racing as the field of battle.

The movie features a rather convoluted plot filled with twists and turns. Considering the memorable characters and the historical setting, it’s little wonder that it has gained a cult following and is still extremely popular to this day.

4. God of Gamblers – Fans of Asian Cinema Rejoice!

For a long time, Macau has been considered the greatest rival of Las Vegas. That’s why you shouldn’t overlook Chinese gambling movies. The top pick of the bunch is, without the shadow of a doubt, the 1989 classic God of Gamblers.

The movie follows the adventures Ko Chun, portrayed by beloved veteran Chow Yun-fat (Donald Chow). Ko Chun is the eponymous God of Gamblers, a world-famous player famed for winning all manner of games of chance. An accident wipes away his memory and leads to an unlikely team-up with the rather mediocre gambler Little Knife – fans of Chinese cinema would immediately recognise him as Andy Lau, one of the most successful faces of Asian cinema with more than 160 movies on his CV.

The plot here is actually a rather good one, so we will try not to spoil too much. Memorable characters, intense games and some action-packed scenes mean that there is something for everyone here. The movie was so successful, that is spawned numerous sequels, parodies and re-boots, with the latest entry being the From Vegas to Macau trilogy – which has, sadly, turned out rather more mediocre than the illustrious predecessor.

5. Owning Mahowny – The Serious Take

If you are looking for a realistic approach to the dangers of gambling, then Owning Mahowny is your best bet. Playing casino games is a great hobby, but it is important to gamble responsibly, as addiction has proven to be a serious problem over the years.

Owning Mahowny follows the misadventures of Dan Mahowny, a stellar bank manager who suffers from a gambling addiction. On the surface, his career is going great and he is in a stable relationship. However, every week Mahowny goes on a trip to Atlantic City, where he uses money stolen from the bank for lavish casino adventures. It’s not hard to guess that very soon, things start to unravel, and our unfortunate protagonist has to face the consequences of his mistakes.

The excellent play of Philip Hoffman and the serious tone of the movie have turned Owning Mahowny into one of the must-see titles for any fan of gambling. It is based on real-life events in Canada, where Brian Molony (notice the similarity?) embezzled more than $10 million from his employers to support his gambling habits.

6. Ocean’s Eleven – Don’t Try This at Home, Kids

We can’t miss one of the most famous gambling-themed movies of all time. A star-studded cast, an action-packed plot and a budget over $85 million ensured that Ocean’s Eleven will be remembered. The story follows experienced heister Danny Ocean on his quest to rob the Bellagio, the Mirage and the MGM Grand casinos in Las Vegas. Naturally, those are all real-life brands that provide high-end entertainment for casino fans.

You will see many familiar faces here. The gang includes George Clooney as Danny Ocean, Brad Pitt as his best friend Rusty, and Julia Roberts as his ex-wife Tess. Matt Damon is also part of the gang, making this his second entry into the list. Veteran Andy Garcia, meanwhile, takes the mantle of Terry Benedict, the owner of the three casinos targeted by Ocean’s Eleven.

Ocean’s Eleven is actually a remake of a much older movie with the same name. The 1960 classic also had impressive production values for its time and featured five members of the famous Rat Pack that consisted of actors and entertainers centred around Las Vegas. Frank Sinatra, Dean Martin and Peter Lawford were among the predecessors of Clooney in this franchise.

7. Rounders – High-Stakes Poker to the Max

One of the highest-grossing stars of American cinema has graced the reels while sitting on rather high-stake tables too. Back in 1998, Matt Damon starred in Rounders, one of the early movies exploring the realities of high-stake poker games. Rounders boasted a cast featuring Edward Norton, John Malkovich and the emphatic Gretchen Mol – but failed rather miserably at the time it came out.

However, the poker craze that boomed in the USA during the 2000s actually brought attention back to the movie and turned it into a cult hit. It follows the adventures of law student Mike McDermott, whose dream is to one day appear in the World Series of Poker finals in Las Vegas. Fascinating high stakes games and strained relationships paint a rather gritty picture of the world of high-stakes gambling.

For its time, the movie offered a good mix between realism and action, with a deeper look towards the strain of high-stakes poker, and some fascinating insights for newbies. Of course, nowadays many more people know that in poker, it is more important to play the people rather than the game, but Rounders used to be an entry point for the general public – besides, how often will you see Matt Damon in a gambling movie?

8. Runner Runner – a Partnership We Can Only Dream Of

Following the early look into high-stakes poker offered by Rounders, we move on to a much more rendition that offers us an insight into the twilight years of the poker boom. This is your only chance to see the unlikely duo of Ben Affleck and Justin Timberlake co-starring together – it’s rather hard to guess who the villain is in advance, isn’t it?

Justin portrays Richie Fulst, an avid poker player, while Ben Affleck takes the role of Ivan Block, who runs the biggest online gambling network in the world. Without getting into any spoilers, their chemistry is great, and the duo gives us a fascinating look into the underworld. Legal issues, fraud, statistics – a curious cocktail set in the luscious landscapes of Puerto Rico (even though most of the action is supposed to take place in Costa Rica).

The star ensemble is a guarantee for great entertainment, but the movie is also one of the most informative you will find on the net. The online poker industry was in full bloom during the 2000s, but several big fraud scandals severely hampered its development and forced much heavier regulations upon players and owners. A lot of the details in Justin Timberlake’s gambling movie are based on the life of former accountant Nat Arem, who did use a statistical approach to prove the work of cheats in online poker rooms.

9. Casino Royale (Again) – The Cheesy Classic

The Casino Royale is such a cult title in gambling movie history, that we would like to enter it a second time – however, this time we will take a step away from Daniel Craig’s cold stare and travel back in time to 1967. The original Casino Royale is quite a different beast from the modern remake and deserves its own place in our ranking.

To be honest, this is the most controversial entry to our list. Casino Royale is not a good movie, not by a long shot. It is overindulgent and quite wasteful with a budget that was considered bombastic for its time. The movie did extremely well thanks to the cult James Bond following, but following a bad critical response, it is considered one of the weaker entries in the franchise and David Niven fares rather badly in most Bond actor rankings.

But – and that’s a big but – the movie is fun. Cheesy fun, of the sort best enjoyed during a pizza night with friends. The over-the-top acting and the weird visuals make for a surprisingly good combination if you are looking for something different. The 1967 Casino Royale is also quite different from the 2007 gambling movie. The two titles show just how much the world of gambling has changed over the last few decades – for starters, you will notice that in 1967, baccarat was still considered more mainstream than poker!

10. The House – How to Run a Casino in Your Basement

With Will Ferrell in the starring role, you can rest assured that this gambling movie will be one hell of a ride. This is one of the latest entries in the ranking and offers a much less serious tone that some of the previous entries. In dire need of money to fund their daughter’s tuition, the husband and wife duo of Scott and Kate Johansen decide to follow the advice of their neighbour Frank and launch an underground casino.

Considering the ensemble of expert comedians – Will Ferrel, Amy Poehler and Nick Kroll to name a few – you can probably guess what the genre is. The House is a straight-up comedy, with a few scenes of violence played for laughs as is the norm these days.

The movie offers a cursory glance at the complexity of running a casino but doesn’t delve too deep in the matter, aside from an occasion of card-counting – which has already been explored in much greater detail in 21. Still, it is what you would expect from Will Ferrel’s gambling movie and fulfils its purpose perfectly. If you want to have a good time without things getting too serious, then this is a definite pick.

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