The world of sports offers much in terms of entertainment to fans and bettors alike.

There’s so much to enjoy when betting on sports, including watching some of the best documentaries ever made.

Sports betting documentaries offer valuable insight into the world of strategizing and markets – including how not to go about the business when wanting to win.

Below are some of the most remarkable documentaries ever produced about this exciting world of amusement and thrills.

60 Minutes – Billy Walters

Billy Walters is a retired businessman and bettor – and a man widely regarded as one of the most successful, but also controversial, gamblers of all time.

With a winning streak that spanned more than 30 years, Walters managed to amass an incredible net worth of $100 million.

This famous punter soon became a legend not only in Las Vegas, but also all over the world. Not only was he a keen sports bettor, but he also won frequently at Roulette – so frequently, in fact, Las Vegas casinos soon became convinced that he wasn’t doing so legally. A group of casinos even took their complaints about Walters to the Gaming Control Board.

For a special insight into the mind and shenanigans of Billy Walters, CBS’ 60 Minutes profile on one of the greatest sports bettors of all time is a must-see.

Now Place Your Bets

Full-title, “Now Place Your Bets: The History of Sports Betting in America”, is a 90-minute documentary first released in 2017.

The doccie takes the viewer all the way back to where and how it all started in the United States. It also offers a valuable insight into how and why sports betting has become as popular as it has.

The documentary is free to watch on YouTube.


If you’re interested in how sports betting got to be legal in the US, then this 2019 documentary will make for riveting viewing.

Action follows the sports betting industry as it adapts to the Supreme Court decision that shone a new light on everything from rogue sportsbooks to honest oddsmakers during the 99th season of the NFL.

The series is made up of four episodes and details the real lives of professional gamblers and those who make a living from setting the odds.

Life On The Line

Released in 2013 and available on Amazon Prime, Life on the Line covers some of the biggest names in sports betting to date.

The documentary includes exclusive and personal appearances by Las Vegas oddsmaker Jay Kornegay and sports radio hosts Ken Thompson and Brian Blessing.

It offers 52 minutes of extraordinary access to the typically closed world of Las Vegas Hotel’s “Super Book” as it prepares for the biggest betting extravaganza of the year: the annual Super Bowl.

The Best Of It

The Best of It takes an in-depth dive into the lives of famous pro-gamblers Alan Denkenson, Ken Weitzner, and Alan Dvorkis.

Produced by Scott Pearson Eberly, it focuses on the 2010 NCAA basketball tournament, and offers an honest insight into the lives of professional bettors and gamblers.