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10 Best Sports Betting Movies Ever Made

Canadians love watching the thrill of gambling, especially those who know the experience firsthand.

While there are countless movies and tops about the struggles and adventures of the casino world, the sports betting niche needs a ranking of its own.

Although the main actors cast in movies are generally handsome and intelligent, don't be fooled by appearances!

These movies don't all end with a peaceful home in Hawaii and a happy family. Instead, some of them are more focused on the materialization of risk-taking.

Without further ado, let's get into what matters - the best sports betting movies!



The Day the Bookies Wept (1939) with Joe Penner and Betty Graves


This American comedy stands as a classic sports gambling movie. Even though its premise is quite silly, "The Day the Bookies Wept" offers a fun perspective into the sheer luck of some gamblers.

Risking it all


"To play or not to play" is the main issue at the start of this movie. The taxi drivers with the Colonel Cab Company are tired of losing bets and money, so they decide to try another approach to horse racing.

They delegate Ernest Ambrose to take a trip to Kentucky to buy a fantastic horse and use it to win on the tracks. 

However, Ernest is tricked into buying a worn-out horse named Hiccup on his arrival. Although the horse's performance on the racetrack fails to impress, Ina (Ernest's girlfriend) overhears what makes Hiccup decimate its adversaries - getting drunk!


Hardball (2001) with Keanu Reeves


This is a sports gambling movie that aims straight for the heart! After hitting a home run with "The Matrix," Keanu Reeves appears as a sports betting addict with a beautiful redemption arc.


Young and troubled


The movie begins with Conor O'Neill (Keanu Reeves), a young man with a gambling addiction.

His debts are growing, and uncertainty and fear take over him. In hopes of getting out of this situation, he decides to take his friend's offer and train a young and troubled baseball team.

To his surprise, the kids respond well to his attitude and quickly begin winning matches they never thought possible. This encourages Conor to take action and resolve issues in his own life.

He falls in love with Wilkes, but the gambling issues hang heavy over his head. Conor has to take a risk in order to fix what he's done and lead the kids to baseball victory!



White Men Can't Jump (1992) with Wesley Snipes and Woody Harrelson

Ron Shelton gives us this American comedy about two streetball hustlers who make money on the assumption that "White Men Can't Jump."

Aside from betting problems, this movie incorporates a love story, a friendship journey, and interesting revelations.


Betting on friendship


Billy Hoyle (Woody Harrelson) is a talented basketball player who hustles those who believe he can't play. This is how he meets Sydney Deane (Wesley Snipes), a great but cocky basketball player.

The two engage in a tumultuous friendship based on sports betting and trickery. This leads Billy's girlfriend (Gloria) to leave him.

After a massive effort on Billy's part, Gloria agrees to give him another chance. However, their relationship is shambles when Billy decides on a last huge bet.


Uncut Gems (2019) with Adam Sandler and Julia Fox

This movie may not be as fabulous as "Breakfast at Tiffany's," but it also involves expensive gemstones and jewelry. Don't worry; sports betting is also included!


Sports betting mania


"Uncut Gems" is filled with lies, deceit, and death - in just the right amount, of course!

Howard Ratner, a money-hungry jewelry shop owner, gets his hand on an opal gemstone that serves as an incentive for action.

The story develops with Kevin Garnett, a star basketball player who insists on keeping the opal for luck.

Throughout the movie, Howard continues the pursuit of money through sports gambling and disregards any character development.

The end of the film leaves the viewer with an intense revelation on people getting what they deserve."


The Gambler (1974) with James Caan and Paul Sorvino

Inspired by the book with the same name written by Fyodor Dostoevsky, "The Gambler" covers a story of sports betting and life gambling. 

The ending may be a mystery to many viewers, but the journey is worth it!


The gambling mob


"The Gambler" begins by showing how anyone can get into betting, no matter the profession. It follows the story of Axel Freed, an English professor who loves gambling.

Although it only brings him debt, Axel seems to enjoy his life's dangers.

The action develops when the English teacher wins a fixed Lakers game. However, the consequences take him by surprise when he attracts the attention of influential mob people.


Diggstown (1992) with James Woods and Oliver Platt

"The muscle, the hustle, and the scam" are words used to perfectly describe this movie.

It involves jail, box, hustling, and sports betting. If you like watching risky boxing movies, this one is for you!


The winner takes it all


When Gabriel Caine (James Woods), a con man, gets out of jail, he decides it's time for his next scheme.

Along with his partner, "Fitz" (Oliver Platt), he travels to Diggstown - a place famous for its boxing obsession.

After an initial deal, Gabriel employs an old friend to defeat anyone from Diggstown who dares to enter the ring.

The fights are entertaining, and a plot twist towards the end reaches a fun conclusion: "Never con a con-man, especially one who's better than you are."


Let It Ride (1989) with Richard Dreyfuss

Hey equestrians, this one goes to you! "Let It Ride" composes enough luck to save every other main character in this ranking.

No wonder why! After all, this movie was based on a book called "Good Vibes."


One lucky day


This movie may have a simple premise, but its action is engaging, fun, and surprising. "Let It Ride" is the kind of story a lottery winner could connect to.

It involves a tremendous amount of luck and describes the best day of a sports betting addict. 

How would your life be if you could win every bet you make like Jay Trotter (Richard Dreyfuss)?

This movie takes you on a rollercoaster of personal drama and huge payoffs. It may not be recommended for kids, but luckily betting is age restrictive!


Eight Men Out (1988) with John Cusack and John Mahoney

"Eight Men Out" is a recollection of Major League Baseball's 1919 Black Sox Scandal. The writer and director, John Sayles, managed to release a pretty accurate depiction of the game-fixing events.


A baseball gamble


This movie goes to knowledgeable baseball fans! "Eight Men Out" aims to tell the story of the baseball players who schemed to lose the 1919 World Series.

However, some subtleties may pass over the heads of the uninitiated.

The focus here is on the eight players who deliberately ruined the game for the White Sox. You'll be able to experience their tension, as not every player is part of their conspiracy.

Plot twists arise as well, capturing a bigger picture of everyone involved!


Smart Money (1996) with Santio East

Next, we have a sports-betting uncovered jewel. "Smart Money (1996)" may have been overlooked by many, but it's time to give this indie-looking film its credits.

The Canadian public will love this one!


Undiscovered treasure


This film strays from the usual hotshot actors of Hollywood. Because of this, Alex Hennech's production flew under the radar, and most people ignored it for the lack of recommendation.

However, this movie's aesthetics and unpredictable action make up for its anonymity.

"Smart Money (1996)" has the advantage of an interesting main character (Jimmy). Through him, this movie compares sports betting with stock trading and takes you on an uncertain journey into New York's underground criminal activity.


The Hustler (1961) with Paul Newman and Jackie Gleason

"The Hustler" is a multi-award-winning movie, voted as "culturally, historically, or aesthetically significant" by the Library of Congress in the USA.

Watch this sports betting movie about Pool games, chance, and professional hustling schemes!


The young prodigy


Believing he has what it takes, Fast Eddie Felson (Paul Newman), a small-time pool player, decides to challenge a legendary player, Minnesota Fats (Jackie Gleason).

This famous character interaction marks a story filled with nerve-racking moments and table-turning conclusions.

Aside from it being internationally famous, this movie is a Canadian favorite! The characters are not the only attraction, though.

Its wagering scenes at the Pool table aim to incite even those who are not interested in gambling!




For many Canadians, the experience of a movie marks a family-friendly evening. However, the films in this ranking are not necessarily as innocent as "Paul Blart: Mall Cop." So, you might want to think twice before watching "Uncut Gems" with kids around.

Even so, expect these 10 best sports betting movies to provide unforgettable journeys into the hustle and bustle of sports gambling!