The Best Gambling Documentaries Of All Time

Written by: Webster Lupton , Casino, Gambling, and Sports Journalist
8 minute read
Best Online Gambling Documentaries

Only a few captivating informative films stand out among the many gambling documentaries online. Naturally, I decided to tackle this issue and create a useful list of the best gambling documentaries for new and experienced players.

I’ve spent hours and hours watching good and -really- bad docuseries to come up with the best catalog. They all share a common thread, a valuable lesson that every player should learn. I will explain it later in this article.

Let’s not waste any time and jump right into the list and uncover the ultimate online gambling documentary up to date.

Top 6 Exciting Gambling Documentaries Online

Most of us who love odds and betting know the risks. So those documentaries about gambling that demonize the industry are a no-no on this list.

The hallmark of a good documentary is an exciting narrative intertwined with a valuable gambling lesson. A lesson that will enhance your knowledge or take you on the road to search and learn it on your own.

Let’s get to it.


Inside The Edge: A Professional Blackjack Adventure Documentary Film

The most thought-provoking and detailed gambling documentary you can enjoy is “Inside the Edge.”

The filmmaker Chris Buddy is a college friend of an elite blackjack player called KC. Buddy travels around the United States, filming KC’s journey at every casino he can find.

The documentary is entertaining because it shows you the highs and lows of gambling across different states. It also shows you how brick-and-mortar casinos will do anything to win. They will use the most ruthless tactics to keep advantage players from beating them.

The film has detailed blackjack information, including KC’s system to bet, double down, and eventually beat any casino in his way.

You leave knowing that it is a grind but also that there are formulas that will help you win big. It’s an excellent documentary.

  • Our rating: 8.0/10
  • Topic: Blackjack
  • IMDB rating: 7.2/10
  • Duration: 1 hour & 56 minutes
  • Where to watch: YouTube

Bet Raise Fold: The Story Of Online Poker

If you are like me and used to love sitting in front of the TV watching poker on ESPN in the early 2000s, this gambling documentary is for you.

It’s basically a time machine for those of us who used to love playing poker in our youth, trying to become the next Daniel Negreanu.

The film talks in detail about the boom period of online poker, its downfall, and the new era. The documentary gives you some nostalgia while highlighting how much things have changed.

The storytelling comes in the voice of Tony Dunst, a professional poker player who earned a TV deal as a World Poker Tour commentator.

Unlike most documentaries about gambling, this film looks professional and well done.

  • Our rating: 7.9/10
  • Topic: Poker
  • IMDB rating: 7.3/10
  • Duration: 1 hour & 41 minutes
  • Where to watch: YouTube

The Best Of It

“The Best of It” follows the life of four high-stakes sports betting gamblers, or what is commonly known as the wise guys.

The documentary centers around Boston, Shrink, Dink, and Banker. These individuals have fought to survive in the cutthroat realm of professional betting.

Each of them has a structure, and each of them has a different lifestyle. Many are married, while others are completely alone on their journey. It gets personal and insightful.

However, the biggest lesson is they all have different betting systems, and they all put in the work. All four wise guys take their sports betting efforts as a full-time job. They talk about how every detail matters to become and stay a winner.

  • Our rating: 7.0/10
  • Topic: Sports Betting
  • IMDB rating: 7.1/10
  • Duration: 1 hour & 58 minutes
  • Where to watch: YouTube

The Player: Secrets Of A Vegas Whale

Trish Regan is a reporter trying to tell the story of a player that beat several casinos for $15 Million in the early 2010s.

The player in question is Don Johnson, a high-stakes gambler who used math and rules to tip the scale in his favor.

Johnson went to the thirsty Atlantic City casino scenery and capitalized on their desperate need for attention.

Atlantic City was losing popularity as other states opened casinos to gain revenue. Knowing that the casinos could use his name to get back on the map, he negotiated unique rules that put him in an unusual favoring situation.

The documentary is clear by saying that a thing like that happens once in a lifetime. Yet, the lesson here is Don Johnson continues searching for an edge over the casinos daily.

  • Our rating: 6.7/10
  • Topic: Blackjack
  • IMDB rating: 6.5/10
  • Duration: 46 minutes
  • Where to watch: YouTube

Frontline: The Fantasy Sports Gamble

As with most PBS creations, this documentary discusses a moral dilemma. The question asked by the filmmakers is: “Is Fantasy Sports part of gambling?”

The documentary interviews people from companies like DraftKings and FanDuel. They vigorously argued that fantasy sports have no connection to gambling.

Funny enough, they shot the film before sports gambling became legal in most states. Now those brands are well-recognized sportsbooks nationwide. They no longer care about the betting stigma now that it is legal.

One person advocating that fantasy football is not gambling gave us a funny quote in the documentary. He said: “It’s more like betting on the stock market.” I guess he didn’t hear himself using the word betting while giving us that remark.

Finally, the documentary shows how the NFL was one of the league’s advocates for the anti-gambling bill created in 2006. Now the NFL is in bed with all the gambling companies.

The lesson here is never to allow corporations to bully you morally. In the end, the gambling money seduced the NFL, just like the rest of us.

  • Our rating: 6.5/10
  • Topic: Fantasy Sports
  • IMDB rating: 6.7/10
  • Duration: 54 minutes
  • Where to watch: Public Broadcasting Service (PBS)

A Kid’s Game: The Story Of Online Poker

Filmed during the golden era of online poker, “A Kid’s Game: The Story of Online Poker” captures the journey of at least ten young poker players. These individuals seek to make a living by playing the game.

The documentary could have better video quality, but it shows how easy it was to succeed in poker 10-15 years ago. It also shows how carefree the lifestyle used to be for most of the protagonists.

Current high-stakes cash players like Isaac Haxton and Andrew Robl appeared in the film, yet the rest of the cast didn’t have a happy ending in the industry.

One thing that stayed with me about this documentary was a quote that says: “Most players think they are better than they actually are.

Considering only two players stayed on top of their games, that quote was on point.

  • Our rating: 6/10
  • Topic: Online Poker
  • IMDB rating: 6.7/10
  • Duration: 1 hour & 10 minutes
  • Where to watch: YouTube

The Lesson Behind These Casino Documentaries

Best Gambling Documentaries icon

At the start of this article, I promised a lesson that every player should learn, and here we are. But you know the lesson already. You know it well. Yet, most unsuccessful gamblers just look away and don’t take it seriously. That’s why they are unsuccessful.

The main lesson I learned by watching all these gambling documentaries is that the key to winning and staying a winner vs. losing everything is… bankroll management.

I know it’s a boring lesson. But so is everything you learned at school. That’s why it’s called a lesson.

This is a topic that every gambler discusses in these films. They are emphatic about the connection between bankroll management and their lifestyle choices. When they talk about bankroll, it involves gambling money and how to deal with winning.

Most gamblers will create a bigger fortune than they have ever seen before, only to blow it in the following days by betting recklessly.

Bankroll management is the key to success.

If you like our list of best gambling documentaries, check out our list of gambling movies on Netflix!

Gambling Documentaries FAQ

If you still have questions about the best gambling documentaries, explore our FAQ section!

What are the best gambling documentaries?

“Inside the Edge” and “Bet Raise Fold” are the two best gambling documentaries you can find online.

What is the most popular gambling documentary?

“Inside the Edge” is the most popular and insightful documentary available.

Where to watch gambling documentaries?

Many of the gambling documentaries are on YouTube.

What gambling documentaries can you watch on Netflix?

“The Untold: Operation Flagrant Foul” is an original gambling documentary that you can watch on Netflix.

Webster Lupton

Webster Lupton Casino, Gambling, and Sports Journalist

Webster Lupton is a journalist and expert sports and casino writer with over 30 years of experience. He is a seasoned researcher and a published author that enjoys the outdoors and birdwatching.

Learn More About Webster