Best Gambling Documentaries оf All Time

Gambling is one of the most popular pastimes in history with people around the world engrossed in playing cards, pulling slots and betting on sports. From the world’s largest gambling cities like Macau in China, Las Vegas in the USA and Monte Carlo in Monaco, the explosion of online gambling and top gambling sites has only increased participation.

Casinos themselves are fascinating places where high rollers and penny slots players alike rub shoulders in a highly-charged atmosphere where people can land life-changing amounts of money. In this piece we are looking at the best gambling documentaries of all time to pull back the curtain on this practice which dates back to the Old Stone Age…

• Louis Theroux: Gambling in Las Vegas
• Gambling Addiction & Me: The Real Hustler
• The Best of It
• Bet Raise Fold: The Story of Online Poker
• Inside The Edge: A Professional Blackjack Adventure Documentary Film
• Out of Luck
• 30 For 30: The Legend of Jimmy the Greek
• The Player: Secrets Of A Vegas Whale

Louis Theroux: Gambling in Las Vegas

Louis Theroux – acclaimed British-American documentary-maker – took his unique style of interviewing to Las Vegas in 2007 to delve into the world behind the myths of casino culture and produce this documentary about gambling. Vegas was the fastest growing city in America at the time and Theroux wanted to explore the pastime and people that have made it an internationally renowned resort city with the nickname ‘Sin City’.

He bases himself at the Las Vegas Hilton – now known as the Westgate Las Vegas – which was once the biggest hotel in the world and combines the old-school charm of Vegas with a modern look. Over one very memorable long weekend he explores all the excitement this casino hotel has to offer, and among the people he encounters include two of the casino’s high-rollers and an employee who looks after them as well as a retired doctor who believes she has gambled away around $4million.

Richard Wilk is the Hilton’s smooth-talking ‘super-host’ who has made it his life’s work to say yes to his clients, whose requests stray into the outrageous and ridiculous. Louis gets to hang out with the high-rollers under Richard’s watch, who are referred to as ‘whales’ like Allan, who jets into Vegas from Canada to party in a $25,000 suite and willingly blow $200,000 or more over the course of just one weekend.

He interviews Dr Martha Ogman, the former doctor and glamorous septuagenarian who spends at least $1,000 a day playing slot games and hasn’t missed a day in 10 years. She can’t hide her delight at her husband’s memorial service being held at the casino because it didn’t cost her a penny. And he is taken under the win of Vegas regulars John and Tim who encourage him as he nervously gambles some of his own money during a long night on the blackjack table.

One of the best gambling documentaries around, Theroux examines the psychology of gambling addiction and the devastating impact it can have on the individuals who pursue it as well as their friends and families. He shines a light on the tactics implemented by casinos to keep their players coming back for more, which include various different loyalty schemes and of course free drinks. As well as exploring the gambling industry, Theroux takes a wider look at the social and economic issues affecting the city of Las Vegas such as homelessness and poverty.

Receiving largely positive reviews, Australian tabloid The Sydney Morning Herald summed it up well by commenting: “There’s an element of prurient ogling at the sheer, mind-boggling waste but Theroux also attempts to unravel the troubled relationship between the largesse the casino bestows upon its favorites and the resulting gratitude and loyalty of the gamblers – many of whom fall into the “addicted” category, much as they would deny it.”

Gambling Addiction & Me: The Real Hustler

Another of the best gambling documentaries from Britain, this film involves Alexis Conran, an expert poker player who collects playing cards – owning over 5,060 decks – and spends up to an hour a day practicing card tricks. Born in Paris, France, Conran’s father was a gambling addict who turned to a life of crime by becoming a thief and conman committing fraud to get money for betting before eventually being arrested and being sent to prison for his crimes.

So while he is thoroughly at home on the casino floor, Alexis is personally interested in understanding the tipping point that turns the odd bet into an addiction. How most people can enjoy their time betting and then simply walk away, while for others it can cause them to ruin their own lives. In the documentary he travels across Britain, to Las Vegas and Athens in Greece – he grew up in the country – meeting gambling addicts, experts and even members of his own family to try and explain what it is that makes gambling such a compulsion for some.

He also covers how casinos and other companies are trying to stem the tide of gambling addiction and help to prevent more people from suffering as well as supporting those who are struggling. Released in 2012, the short documentary pays particularly close attention to what makes vulnerable people engage in gambling to begin with.

The Best of It

Directed by Scott Pearson Eberly, this unique documentary about gambling takes an unflinching look at what it takes to be a professional gambler, focusing on the lives of four sports bettors known as Boston, Dink, Banker and The Shrink, who have all fought tooth and nail to get where they are.

• Boston: Iconic college basketball betting guru that has been placing wagers on sports in Las Vegas for over 30 years, he is old school and proud of it, refusing to embrace modern methods and continuing to bet with gut and feel as well as his personal power ratings that can be found in a three-ring binder.
• Dink: Gambling lover who credits much of his success to his early 20s as a bookmaker in Queens, where he learned the hard way getting cleaned out by the ‘Wise Guys’ (successful professional gamblers). After serving time in a halfway house he moved to Las Vegas and 21 years later gambles on sports year-round from his home in a gated community.
• Banker: Lem Banker arrived in Las Vegas when it was still mob-run in the 1950s and became connected with some of the murky figures that ran the town. He organized a few sportsbooks and became close with Lefty Rosenthal – the man Robert De Niro’s character in the film Casino is based on. But it wasn’t until the 1980s when he became a great gambler himself, operating with a team of bet runners and a network that provided him with inside information on injuries so he could beat the bookies.
• The Shrink: Getting his name from time spent pursuing a career in psychology, he built the biggest sports betting forum site in the 1990s and became a therapist of sorts on the message boards. He also brokered relationships with offshore sportsbooks before they were cracked down on by the government and believes bankroll management is key to the longevity of a successful gambler.

Rather than glorifying the lifestyle, the film showcases the many challenges and battles the four men face, who are all well aware that this profession is unforgiving – we’re told the house always wins after all.

They each have their own specific structure and way of playing while some are married and others single – but you are left in no doubt that these people are not your everyday gamblers. They treat betting as if it was a full-time job and outline how important every detail is in order to become a winner and stay that way.

A feud develops between Boston and The Shrink over accusations that are made about gambling debts, despite the many rumors and half-truths circulating. The documentary’s name ‘The Best of It’ comes from the widely-used sports betting term that refers to any bet where your expected value is positive.

Bet Raise Fold: The Story of Online Poker

Bet Raise Fold is an online gambling documentary set during the poker boom of the early 2000s, following a generation of internet poker pros who honed their skills online. One of the best casino documentaries out there, we are treated to an inside line on the lives of these players and exactly how the United States government eventually turned their lives upside down on a day that became to be known in poker circles as ‘Black Friday’.

Narrated by Tony Dunts – a professional poker player who landed a TV deal as a World Poker Tour commentator – the film highlights how intelligent and talented this online generation were, focusing on three likable players as well as interviewing some of the finest minds in the game. We witness all the build-up to the dramatic day of April 15th, 2011, that radically changed the industry and how far-reaching the consequences were.

Inside The Edge: A Professional Blackjack Adventure Documentary Film

One of the best gambling documentaries about blackjack ever made comes from film-maker Chris Buddy who gives us an unprecedented glimpse into the world of elite blackjack players who take on the casinos to win millions of dollars thanks to his college friendship with a high-profile card-counter known as KC. They travel around the US and overseas filming their exploits at casinos, showcasing the great lengths the house will go to in order to stop advantage players from beating them.

Because he has been banned from so many casinos KC has to change up his look on a daily basis in order to not be spotted by casino surveillance systems and security personnel. Here we see the truth of being a top-level blackjack player and the inevitable boredom, loneliness and downswings that come with it. KC is brilliantly honest too, admitting: “My career playing blackjack, I’ve had many, many days where I’ve both won and lost hundreds of thousands of dollars. It’s quite an emotional rollercoaster.”

Out of Luck

Delving into the American lottery system, Out of Luck looks at why these are so widely played in the US and how they may be even bigger than traditional casinos deliberately aiming to profit from poor and vulnerable people. We see players that have lost so much to the lottery – bursting the myth that players only lose small amounts playing – with some truly haunting footage and heartbreaking back stories.

The documentary about gambling also outlines the statistics involved such as 80% of all lottery profits are made up of just 15% of the players making it clear that a small minority make up most of the money. Director Bert Klassey focuses on the story of one man who owned a convenience store in the US but ended up going bankrupt because he spent over a million dollars on lottery tickets.

30 For 30: The Legend of Jimmy the Greek

This 2009 film follows the career of legendary sports commentator Jimmy Synder who helped to legitimize betting on NFL games by finding different ways of giving points spreads during pre-game shows. Back in the 1980s the show NFL Today on channel CBS combined reporting, analysis, predictions, humor and talent in an era before sports betting in the States was legal.

The biggest star was Jimmy’ The Greek’ Snyder who was born in Ohio to Greek immigrants and overcame childhood tragedy to move to Las Vegas and become one of the key figures in the world of sports handicapping. Peabody Award-winning film-maker Fritz Mitchell takes a unique look at Jimmy’s unique rise to respectability and tragic downfall, conducting interviews with his friends, family and co-workers to paint a vivid picture of this larger-than-life character.

The Player: Secrets Of A Vegas Whale

Trish Regan tells the story of ‘whale’ Don Johnson who beat several casinos in the early 2010s to make around $15m in this 46-minute documentary. Delving inside some of the most famous casinos that make up the Las Vegas strip, we hear from the man himself on how he found an entirely new way to beat the system in blackjack.

Johnson’s brilliant understanding of game theory allowed him to work out unique weaknesses in casinos and develop innovative techniques in order to gain an edge over the house. His methods have since become known as ‘the Don Johnson way’, including pressurizing dealers into making mistakes and being rewarded with free bets.