Sportsbook Movies

Even though most of the films coming out of Hollywood today are pure fiction with not a whole lot of truth involved, every now and then one of the industry giants somehow gets it right and releases a movie that truly captures the world of gambling as you’ve never seen before. Below are the top five sports betting movies of all time including what they were about, and why our staff loves them-

Diggstown (1992)
Genre- Boxing, Sports Con Artists

While Diggstown may be more about boxing and con artists than actual sports betting, we simply could not think of a better title to start with since this film has it all. Not only is it unquestionably the funniest gambling movie that you’ll ever see but it also gives an inside look on how corruption can easily find its way into sports betting from several different angles. James Woods and Louis Gossett Jr. are phenomenal in this film and we really think you’ll enjoy it.

Two for the Money (2005)
Genre- Handicapping

Two for the Money takes an inside look at the side of sports betting that most people do not see; the inner workings of the professional handicapper. Al Pacino, a professional pick expert with thousands of sports betting clients, seeks out small town prodigy Matthew McConaughey because of his recent hot streak in numerous sports. The duo make millions while things are going well, but when the tables start to turn it gets downright ugly for everyone involved.

Bookies (2003)
Genre- Sports Betting

Bookies features Nick Stahl, Johnny Galecki and Lukas Haas as three college students that dive headfirst into the world of sports betting as a means of paying tuition. Things start off well for these local campus bookies but as the wagers grow in size, they find themselves on the edge of their seats as they win and lose several close calls. Instead of leaving the world of sports betting to chance, the trio decides to fix a series of basketball games on campus…and that’s where this title really starts to get interesting.

Eight Men Out (1988)
Genre- Baseball Corruption

If you’re a baseball fan then you probably know all about the 1919 Chicago Black Sox and their dive in the World Series, but what you probably didn’t know was that they were offered more money in one game than most of their players made in a single year. This portrayal of the 1919 team documents the events that led up to the darkest moment in baseball history and leaves the door wide open when it comes to history repeating itself.

Let it Ride (1989)

In the movie Let it Ride, Richard Dreyfuss is a gambling addict that can not seem to stay away from the horse tracks. He promises his wife that he’s finished with the sport forever, but then an unlikely tip comes in and he decides to have one last day at the track. After Dreyfuss wins his original bet, he decides to “let it ride” since it’s his last chance to win big at the tracks. This turns out to be an excellent film that leaves you wondering, “How far can we really trust our luck and instincts?”

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