Top 10 Gambling Documentaries

Gambling is fascinating, so it was inevitable that documentaries would be made on various aspects of the hobby.

With an old and rich history behind it, there have been countless stories of the complexities in the industry and the people who dared to take risks and win.

Real people going through real struggles, be it from fame, addiction, or risk, are what put a human face behind the industry, which is often looked at as a vast and untouchable entity.

The media also portrays the hobby in many different ways, but they are hardly true stories. 

Let’s take a back seat and get an insight into the gambling universe through these 10 documentaries.

10. High Roller: The Stu Ungar Story

[Source: amazon.com]

People who love competitive poker have definitely heard of Stu Ungar. Being one of the most recognizable faces of the sport in the 80s and 90s, this documentary delves deep into the life and mind of the legend himself.

The short film takes into account everything from his meteoric rise to his eventual death and brings us the complete story of the man behind the legend.

It talks about his charisma and exceptional talent, which made him a hero to many, the darker aspects of life that the fame brought, like his tumultuous relationships, and Ungar’s slow descent into addiction.

The documentary also captures his later decline, where he struggled with relapse and rehabilitation and a declining gambling career. In the end, the documentary is a bittersweet look at the brilliance of Stu Ungar and takes the audience through the rollercoaster journey that was his life.

9. Out of Luck

[Source: toddsoliday.com]

We have seen the boom in the lottery in the past decades, and Out of Luck is a documentary that focuses on just that. The short film threw out facts and made arguments that made people take a backseat and really think about the state of lottery games, especially state-owned ones.

The documentary talks about the studies that show that most of the people who buy lottery tickets are from a lower socio-economic background, and they make up most of the profits. Facts like nearly 80% of the profits come from the same 15% of players go to show how deeply lotteries have affected the poor and uneducated.

The show also brings in gamblers who participate in these lotteries to tell their stories and how they deal with addiction.

There are also several experts who bring facts and data to the documentary, making it perhaps the most thorough study ever done on lottery gambling. The film also asks the question of whether or not it's okay for a state to run gambling operations to get money.

8. The Player: Secrets of a Vegas Whale

[Source: amazon.com]

We are always quick to admire high rollers who stroll into the casino and bet tons of money without breaking a sweat. The Player is a documentary showcasing the life of one such gambler named Don Johnson.

He is one of the most successful blackjack players in the world.

This select group of high rollers, also known as whales," bet enormous amounts of money, and Johnson was one of the most recognizable among them.

The documentary goes through his humble beginnings and how he got started with gambling. You also see how he transformed into such a prolific blackjack bettor and garnered success.

Viewers go through his calculations, strategies, and negotiations as he goes through various casinos in Vegas and Atlantic City, increasing his odds and winning millions. You can also see the high life in person that is so often relegated behind closed doors.

7. Frontline: The Fantasy Sports Gamble

[Source: imdb.com]

With the advent of fantasy sports betting, companies were experiencing a significantly high number of bets even when laws were being enacted to crack down on it.

The New York Times assisted this project by going to the roots of online sports betting and giving us an inside look at these multi-million dollar operations.

At a time when governments were playing catch up to the industry, this documentary goes deep into this unregulated and free for all world.

The Frontline series has been running for many seasons, and this deep, insightful look comes to us on season 34, episode 3. The documentary also looks into the taxes, licensing fees, and profits made by the companies that came from entertainment.

For a thorough and deep understanding of the sports betting world both in the US and abroad, The Fantasy Sports Gamble is a must-watch. The murky waters of people betting on actual players being put in fictional scenarios are as intriguing as it gets.

6. Sports Betting: Billy Walters

[Source: amazon.com]

Anyone even remotely interested in horseracing has heard the name Billy Walters before. Known as the most successful sports bettor in Vegas, Walters has made big moves and won even bigger amounts, reportedly winning $3.5 million in a single superbowl bet.

The famous 60-minute episode goes through his childhood and how he started betting, from simple street bets to being feared by the biggest sportsbooks in Vegas.

CBS News takes us right to him, and we get an insight into the life and mind of this legendary gambler from his own mouth. The short documentary shows us how he perceives odds and bets accordingly with his intricate handicapping methods.

With three decades of successful betting behind him, where he reportedly never lost a single bet, this documentary is a must-watch for sports bettors as you hear how the most successful sports bettor got his start and created his legacy.

5. The Best of It

[Source: imdb.com]

Rivalries in gambling seem all too common, with big-name celebrities in the sport coming together to challenge each other during world-class events. The Best of It is a documentary featuring four such gamblers and their stories of making it big in this competitive hobby.

The documentary also delves into the psyche and personal lives of these gamblers, which very few documentaries have ever done. The ups and downs in their lives that came with gambling led them to take on a new life by themselves.

We also see the sheer numbers game that sports betting can be at the very top and how gamblers have to take in every detail.

By putting people who love and cherish the sport enough to put it at the forefront of their lives, The Best of It gives us a raw insight into the world of high-stakes betting. It is definitely a must-watch for both rookie and experienced sports bettors.

4. Bet Raise Fold

[Source: imdb.com]

A lot of us may not remember how quickly online poker came into the gambling scene and took over a sizable chunk of the gambling industry. Bet Raise Fold goes through all the proceedings that led up to the online poker boom and the events succeeding it.

The documentary provided all the reasons why online poker took over and brought forward the story of three individuals who used the sport for their own benefit, like helping support their families and traveling the world, just to name a few.

It also took us through the aftermath of all this, including the infamous "Black Friday" event where the US government banned all online poker sites.

For an in-depth look at the birth, rise, and subsequent stumble that online poker experienced, Bet Raise Fold is an excellent watch.

The short film also lets viewers see the rise of new stars online who would change the poker scene forever and leave a lasting impact that we feel to this day.

3. Gambling Addiction and Me: The Real Hustler

[Source: habwin.com]

Although gambling is an exciting and glamorous activity, as with anything, it can take quite a toll on you if not regulated. Gambling Addiction and Me is a raw and unapologetic look at how the hobby can be destructive when it becomes an addiction.

We follow the story of Alexis Conran’s father, who has to take on his inner demons and face his gambling addiction.

The deeply personal and harrowing journey does have a silver lining in the form of redemption and a better life. The documentary also has several people fighting their addictions and their stories, which adds to the deeply human element that the story wants to portray.

Writer Conran might be portraying a very emotional story, but none of it is inaccurate, and he also puts his biases aside to showcase how casinos are working on preventing people from getting addicted to gaming.

2. Breaking Vegas

[Source: imdb.com]

The MIT Blackjack team is one of the most recognizable elements in the recent history of gambling, and their escapades remained shrouded in mystery for decades. Breaking Vegas is a documentary that targets the team’s every move and brings forward the challenges the infamous team faced throughout the time they were active.

Throughout the short film, we see how these expert mathematicians exploited the loopholes in casinos throughout the US.

We also get an in-depth look at card counting and how the team employed the tactic to amass millions by managing and adjusting their bets. The documentary dives into the tactics that casinos employed to break these players as they became famous, be it in the form of surveillance and security or mind games.

The documentary then questions the audience about whether card counting is a skillful display of tactics or gets into the territory of cheating. Being a hotly debated topic, the film lets you come to your own conclusion and is an entertaining watch-through and through.

1. The Legend of Jimmy the Greek

[Source: imdb.com]

The entire sports betting community owes a lot to James "Jimmy the Greek" Snyder, a sports commentator and pioneer of gambling in the US. Snyder’s life is put on display from his first appearance in the NFL pregame show to his controversial remarks and finally his contributions to gambling.

Snyder’s early life is put on display as you see the young and charismatic commentator break down games and analyze them to make accurate predictions of events.

As he grew popular, his tactics and predictions would give rise to a substantial community of sports bettors who followed in his footsteps and made gambling on sports more mainstream among the US public.

In the short film, you see everything from his contributions to legitimizing sports betting in the US to his controversial remarks and subsequent fall, which came quickly afterward.

His impact on future generations of sports bettors is also discussed, and you see how betting on sports went from a taboo to an occasional and acceptable form of entertainment.

Conclusion

Unlike movies, documentaries are often an excellent way to not just be entertained but also be informed. In an ever-evolving industry like gambling, you simply cannot afford to miss the hype of new events.

Knowing the origins of the various ways of gambling and how they got started also lets you make future predictions and stay ahead of the curve in terms of new tech or features that might come about.

So what are you waiting for?

Pick up any of these documentaries that you like and get some snacks ready. It’s about time you took a break from life and took some time to relax and watch an entertaining story unfold before your very eyes!