Five Gambling Documentaries You Shouldn’t Miss
By
Kevin Lentz
Writer at Casinos.US Updated: 09/02/2024
Kevin has been involved in the gambling industry since the ‘80s. From winning tournaments to casino management, he’s ultimately done it all. Throughout the years, he’s written for various iGaming publications on topics such as the legal landscape of online casinos and strategies behind winning. His favorite game is blackjack.
Top Gambling Documentaries
Look, I’ve been in the casino business my whole adult life. I’ve spent the last thirty years managing table games and slot departments, even poker rooms, and in the previous few years, we’ve added Sports Books to the mix.
What I think a lot of people don’t understand about the business is its sheer highs and lows, the stupefying amount of time some people spend thinking about it, the dark side of it, and, because it happens increasingly behind closed doors in private salons, the sheer luxury, glamour, and opulence that casinos are willing to shower on their high-end guests.
Now, you’ll note that I didn’t say these are the best gambling documentaries, but these are the ones I bring up again and again when guests ask me about sports betting, card counting, or poker. They are the ones I tell them to watch when they ask about high rollers or the toll that gambling can take on some. I hope you will like them as much as I do.
- 🎬 What Are Five Great Documentaries About Gambling?
- 🎬 The Player: Secrets of a Vegas Whale
- 🎬 Bet Raise Fold (2013)
- 🎬 Inside The Edge (2019)
- 🎬 The Best of It (2016)
- 🎬 Gambling in Las Vegas (2006)
- 🎬 The Trouble With a Gambling Documentary
What Are Five Great Documentaries About Gambling?
When you sit down to watch a gambling documentary, you want to peel back the covers and understand what is really going on, to come away with a sense that you have learned something new.
Something that you never understood before, and especially when we watch shows about gambling, we want to feel like we are there, like we are part of the action, like we made that wager ourselves.
I like to think that all these gambling documentary recommendations meet that criteria and showcase a world that is both fascinating and a little bit scary.
The Player: Secrets of a Vegas Whale (2014)
This one is a keeper because it not only shows you the over-the-top spectacle that is Las Vegas when they believe you to be a million-dollar sucker but also how some smart suckers have managed to take these over-eager casinos for a ride.
Have you ever wondered how much you need to gamble to control the button for the Bellagio fountains? Have you ever wondered if you could quietly beat the casinos at their game own game while they wine and dine you and put you up in $50k suites? This is the film title you will be telling your friends about.
Bet Raise Fold (2013)
You can’t tell the story of gambling in the 21st century without telling the story of the online poker sites and their subsequent boom and bust in the early 2000s. And Bet Raise Fold does that very well. Shot through the eyes of three players, this gritty inside-the-action film shows you what it was like to be a poker player in 2004 or 2005.
But then, on Black Friday 2006, the US government basically shut down internet poker. This catastrophe is best viewed by how it affects these players and shown in a way that allows you to see the devastation and pain it causes at an individual level. It’s a great story and one that leads directly into today’s expansion of internet sports books and gambling with some salient lessons.
Inside The Edge (2019)
Any film that has James Grosjean, Michael Shackelford, John Chang, Arnold Snyder, and Tommy Hyland is going to be on our must-watch gambling documentary list. But this one actually manages to show both the highs and lows of card counting. KC, the counter protagonist in this film, also shows the intense loneliness and stress that comes from pursuing this nomadic life on the road.
But Inside the Edge doesn’t blink at showing both the casino and the counter’s tactics, some of which border on illegal, and the cat-and-mouse game that is played out at casinos all over the country every day. For that reason, we think anyone interested in either card counting or what goes on behind the scenes at casinos will love this film.
The Best of It (2016)
There are people who live, eat, and breathe sports betting — I mean, they are consumed with it. Some of these people actually find a way to make a living at it. But as you might imagine, it takes a special kind of person to spend their entire adult life making their living wagering on sporting events.
This movie was made pre-PAPSA, so we don’t get to see how the money lines at the best online casino sites here in the US might have changed their strategy, let alone the dozens of more sports books online offering juicy lines in some states. Maybe they should follow up on it now with the advent of all the internet sports betting. But we do get to see the good, the bad, and the ugly behind serious, professional sports bettors trying to make a go of it in Las Vegas.
Gambling in Las Vegas (2006)
This gambling documentary by Louis Theroux is another hard look at high rollers and the casinos that court them. But unlike The Player, these folks haven’t got an angle. But they remind me very much of the same type of players I’ve run into over the years. So much so, in fact that I will break down and rewatch it every now and again.
I think more than anything, it demonstrates the need to be very aware of the dangers of gambling addiction and the fact that casinos who, in some cases, should know better, often enable marginalized and vulnerable individuals by playing to their vanity and need to feel seen, to be viewed as important. It’s not always an easy watch, but it is a rewarding one.
The Trouble With a Gambling Documentary
The trouble with gambling documentaries is that they are made for a certain audience. A hard-hitting film on addiction and loss will be loved by some and booed by others. A movie about the luxury and opulence of Las Vegas may be panned by those pointing out poverty and homelessness in the city. A documentary about sports bettors may only confuse slot players or casual gamblers with its terminology.
Even a great film that shows both sides of the gambling issue may come under fire due to it being such a hot-button topic. But whether you believe gambling to be a societal ill or can’t get enough of casino life, we hope you will find some entertainment and even some knowledge in our list of the top five gambling documentaries. And that one of them will show you a side of gambling you’ve never witnessed before.
