6 Gambling Documentaries You Should Watch Now

Cover Images for Documentaries Now Place Your Bets and Bet Raise Fold

Hollywood has done a remarkable job of glamourizing what gambling really is. Sure, casinos are a mesmerizing wonderland of overindulgence, but it’s not all fame and glory.

I’m sure you’re familiar with the rags to riches stories to which I’m referring. Maybe you’re more interested in the down and out sports bettor that finds himself on the wrong side of the mob only to find redemption as the final horn sounds.

Regardless of your favorite genre of film, one fact remains:

You have little idea what the gambling life really is.

That is unless you have really lived the life of a professional gambler or have dealt with the woes of problem gambling.

Documentaries Provide A Look Behind the Curtain

The gambling industry has been enjoying a steady rise in popularity and profits for the last 20 years. Filmmakers have also taken notice.

For the novice gambler, these documentaries may miss. However, gambling enthusiasts will find these six gambling documentaries as educational as they are entertaining.

These gambling documentaries will draw you into the lives of gamblers from many walks of life. You can see first-hand the manic highs and lows that come from problem gambling. You’ll float away to day-dreamland on the private jet of the high roller. You can even trudge through middle America with the carefree gambler.

1 – Now Place Your Bets

Now Place Your Bets is a 2017 documentary from the mind of James Bernardo. The film, which features recognizable characters like Pete Rose, Joe D’Amico, and Professor Richard Davies, takes a more in-depth look at the role Las Vegas played in the rise of sports betting as a legitimate industry.

This may be the premier documentary surrounding the world of sports betting. Specifically, it focuses on the rise in the popularity of sports betting in Las Vegas and the United States, where sports betting has always been legal.

By using photos, archival video footage, and face to face interviews with people on the front lines of the sports betting boom, the filmmaker does a beautiful job peeling the curtain on an industry worth more than $100 billion.

Also, the documentary investigates how Vegas played a significant part in the long road that occurred before the sports betting craze. You’ll also gain insight as to exactly how Las Vegas became the mecca for sports bettors in the United States.

Finally, Now Place Your Bets examines how sports betting has embedded itself into the culture in America. Sports betting has become a massive part of not only the gambling world but the fabric of our society.

2 – Inside: Underground Poker

The 2012 documentary Inside: Underground Poker features a cast of colorful characters. I was quickly drawn to the exciting names like Mikey Tats, Brad the Conductor, and John the Banker.

Producer Jon Bulette dives into New York City’s underground poker scene and the fascinating impact that illegal gambling has on player’s lives.

The documentary follows a man, Brad the Conductor, who has turned organizing these illegal poker games into a career. He’s always trying to stay one step ahead of state and federal gambling authorities who would rather shut him down.

The underground poker scene has presented a nightmare for those trying to put an end to such games.

Bulette does a remarkable job of providing a window into the lives of those involved in New York’s underground poker matches and the effect the games have had on their lives.

The filmmaker drew me in by sitting down and asking the right questions. I found myself rooting for these guys. It’s a rare look at the impact felt by the families of these men, and the film was surprisingly emotional.

Isn’t that why films are made?

To feel something.

You may also enjoy seeing the organizers of these games scramble to facilitate players’ creature comforts, including food, drinks, and, of course, women.

Inside: Underground Poker is an obscure and entertaining glimpse into this secretive world.

3 – Bet Raise Fold: The Story of Online Poker

Online poker exploded onto the gambling landscape like nothing I’ve seen. The 2013 documentary Bet Raise Fold: The Story of Online Poker revolves around the genesis of real money online poker, its evolution, and the response by authorities in the United States.

Director Ryan Firpo launches the film with players from around the country, shedding light on the lasting consequences of decisions made by the federal government. The actions of the authorities left a surprising number of people without their money.

In fact, the United States government has clamped down on over $500 million from people around the world as a result of these poker rooms. Three of the people directly impacted by these seizures are interviewed in Bet Raise Fold.

Firpo also explores the legal implications of online gambling in the United States — specifically, how the DoJ (Department of Justice) has continued to take action towards online gambling companies.

4 – Gambling Addiction & Me – The Real Hustler

For Gambling Addiction & Me – The Real Hustler, we head across the pond to the UK. This 2012 film by Alexis Conran gives a personal view of an often private matter.

Conran sets out to find answers as to how gambling addiction landed his own father in jail. He searches to find any evidence whether he could possibly go down the same dark trail.

Gambling Addiction & Me is a real-life look at the wreckage caused by addiction. Alex Conran provides a seldom seen or even discussed perspective on this cunning disease.

You’ll walk with Alex as he searches for understanding and the reasoning behind his father’s actions. The documentary follows a man on the quest for an answer to one question:

What pushes people over that fine line between recreational gambling and gambling addiction?

Several gambling addicts join Conran for interviews. This provides heartbreaking tales of how everyday people like me and you have lost it all.

By all, I don’t mean their bankroll. I think most gamblers have been there. I’m talking about losing it all; houses, spouses, family, careers, all of it.


Alex also draws an essential correlation between the online casinos and the vast increase in the number of people that suffer from gambling addiction.

He ultimately finds himself working with organizations that are trying to shed light on the topic and providing resources for those afflicted.

5 – FRONTLINE: The Fantasy Sports Gamble

Frontline: The Fantasy Sports Gamble is a 2016 collaboration between PBS and The New York Times.

Fantasy Sports Gamble is considered by many in my circle to be among the most forethinking documentaries in the gambling community.

The targets of the documentary are 2 specific sites: DraftKings and FanDuel.

Both companies facilitate fantasy sports betting here in the United States. You’re likely familiar with each company.

However, do you know how they make their money?

Frontline: The Fantasy Sports Gamble gives you an open look at exactly how they operate.

Legal because gamblers were not betting on actual contests, daily fantasy sports quickly became a hugely popular game across the country.

In most areas of the United States, gambling, including sports betting, is strictly prohibited.

But it’s perfectly legal to engage in fantasy sports.

It’s legal because the powers that be have classified it as entertainment. Since it’s mostly unregulated, the door was flung open, and mountains of money began pouring in — all without having to pay any gambling license fees or affiliated gambling taxes.

6 – A Kid’s Game: The Story of Online Poker

A Kid’s Game: The Story of Online Poker is an exciting examination of the daily lives of the best young online poker players on the planet. You get not only a peek into their careers, but also into how online gambling has impacted their lives.

Many people take issues with real money online casinos because of their availability to young people and specifically children. The documentary features several interviews with several players who admit they began playing online poker before they were legally of age to do so.

You are also shown how these players leveraged those early lessons into a successful gambling career. Of course, you are also shown the darker side of online poker. One example shown is what it’s like when one of these young players suddenly loses their bankroll in a game.


I love how much attention the gambling industry and the people that continue to grow gambling has gotten. Sitting down and spending an hour or two learning about the lives of fellow gamblers or about any aspect of my favorite pastime is always an easy sell.

Hopefully, we will continue to have fantastic content brought our way going forward. Meanwhile, take advantage of your downtime and enjoy one of the above gambling documentaries.

Chances are you have the time to watch all six in the coming weeks.