Best Gambling Documentaries: Taking a Look Behind Curtains

  • Learn about gambling through the eyes of filmmakers
  • We collected documentaries on shocking stories, historical winners and more
  • Pick one of our seven favourite documentaries on gambling
best gambling documentaries

What better way is there to learn about gambling stories than from the best gambling themed documentaries? We collected seven great productions from the past years that will give you a great understanding of gambling both offline and online. 

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Gambling has inspired so much in our pop culture. From famous Hollywood movies through songs and saying, the thrill and excitement gave a base to many ideas. Of course, gambling enthusiasts know that the casino and gambling world is often over-romanticized in movies. From time to time, great productions come out to educate and to entertain. Documentaries on gambling show us some details and insights that we hardly have access to. Moreover, it is always great information if you gamble yourself. The topics of course vary. In this industry, we have countless inspiring but also concerning stories. When taking a dive into the best gambling documentaries, expect some shocking revelations. Filmmakers aim to share the stories of great players, exciting stories, problems of addiction and insights into the industry and technology. This article will guide you through all of these with a rich picking of some great movies to watch. 

Popular themes of the best gambling documentaries: 

From the mid-nineties, documentaries on gambling started to become more and more fruitful. Of course, Las Vegas was the number one inspiration for such movies. Back in the day, when brick and mortar casinos were our only options, this peculiar world started to attract not just gamblers but filmmakers. Popular topics feature uncovering schemes and cheats, the mafia’s involvement, and some of the most famous and luckiest players in popular casino games. The best gambling documentaries give off some great detail not only on the objective truth but feature real people’s stories. After the online casino boom from the early 2000s, new themes appeared. The many changes in the industry inspired documentaries solely on online gambling in the US, and also some serious topics on addiction and potential harms. Let’s take a look at the top films you should watch if you gamble! 

Drawing Dead: The Highs & Lows of Online Poker (2013)

2013 film Drawing Dead is a documentary film about the highs and lows of online poker from two very different perspectives: a professional poker player worth millions, and a gambling addict. Director Mark Weeks also narrates the story. The director has his own experience with online poker, hence the inspiration. While Drawing Dead is not exactly impartial, it shows us a very interesting contrast between a success story and someone who never really had the chance to succeed. The film talks about the history of online poker in a new light making it definitely worth watching – of course with a critical eye. 

Bet Raise Fold (2013)

Bet Raise Fold was also released in 2013 and it is quite similar to Drawing Dead concerning the themes they explore. The film gives a great and detailed view of the online poker landscape. The reason we love this film is that it managed to explore the online poker world by following three very different protagonists. The shooting of the film started in 2010, therefore the infamous Black Friday 2011 happened during rolling cameras. Named by the poker community, the 2011 Black Friday refers to a  United States federal criminal case against the founders of the three largest online poker companies. Bet Raise fold is definitely one of the best gambling documentaries when exploring the world of online poker. After watching the film, try your luck on Intertops Poker

Gambling Addiction & Me – The Real Hustler (2012)

This docu is for sure a favourite. While the topic is a very personal and dark matter, it is 100% recommended to watch. Star of BBC Three’s hugely popular The Real Hustle, Alexis Conran is an expert poker player and a man thoroughly at home in a casino, Alexis enjoys the thrill that comes with gambling. For him, gambling is a fun and leisure activity, his father suffered from addiction. Gambling Addiction & Me aims to explore the tipping point where gambling turns into an unhealthy activity, educating all of us on how to avoid it. In this documentary, Alexis travels around Britain, to Las Vegas and to Athens, meeting from a variety of experts through gambling addicts. 

Breaking Vegas: The True Story of the MIT Blackjack Team (2004)

The story of the MIT Blackjack Team is fascinating. It inspired many fictional films, yet this documentary tries to explore the story while staying outside. The MIT Blackjack Team was a group of students and ex-students from the Massachusetts Institute of Technology, Harvard University, and other leading colleges who used card counting techniques and more sophisticated strategies to beat casinos at blackjack worldwide. The team and its successors operated successfully from 1979 through the beginning of the 21st century. Their story inspired many over the years, in a previous article see a detailed story

Inside: Underground Poker (2012)

This documentary is quite different, yet the shocking revelations of the underground poker scene make it outstanding. Documentary – Inside Underground Poker – November 27th 2012. Filmed in New York City for the National Geographic TV channel – A series of underground poker games filled with danger, allure and adrenaline. One of the top games is run by Mikey Tatts who has cultivated a roster including business owners, drug dealer, pimps and professional rounders.

A Kid’s Game: The Story of Online Poker 

This documentary places online poker in the US to a new perspective. It covers a variety of topics associated with being a professional poker player. Including the most money won/lost in a day, how they handle big losing sessions. Also, how their friends and family handle them playing poker for a living, and many more. Many professional players feature in this film, if inspired, take a peek at their life on Intertops Poker!

Our best gambling documentary: Now Place Your Bets (2017) 

Last but not least, probably the best gambling documentary so far: Now Place Your Bets. The film had great success after its release, and quite rightfully so. A very in-depth and detailed overview of how legal sports betting in the US became a billion-dollar industry. The film features many personal interviews, original footage and photos. It guides us through the timeline and key events that shaped the sports betting industry into what it is today. With the rise of online sportsbooks in the US, it is even more interesting the learn about the background and fully understand the development of this scene.

The reason this film is truly outstanding is due to the number of important people they managed to engage. They feature pioneer oddsmakers, casino operators, bookmakers, professional gamblers, journalists and historians who witnessed these events. Furthermore, Now Place Your Bets also targets the psychological and motivational aspects of gambling. Top choice for sure! 

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