The only thing better than betting on sports is movies about gambling on sports. Below are the Top 5 undisputed best sports gambling movies, in no particular order.

1. Casino (1995)

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First of all, what an absolutely loaded cast (Robert De Niro, Joe Pesci, Sharon Stone, James Woods)! This Scorsese film is one of the all-time classics in any genre. Based on a non-fiction book by reporter Nicholas Pileggi, the movie follows Ace Rothstein (De Niro) a gambling handicapper who is asked by the Chicago mob to oversee the Tangiers Casino operations in Vegas. Throughout the movie, Ace battles to maintain his ethics and relationships while operating the casino with heavy Mafia involvement.

The movie can get dark and violent like any good Scorsese film. But it’s an interesting look at the changes in Vegas sports gambling in the 1970s, as it transitioned from underground crime operations to the more corporatized world that we see today. The fact that it’s based on real events (the real Ace Rothstein is considered the sharpest oddsmaker of all time) makes it even more interesting.

Most importantly, it also has Joe Pesci losing his goddamn mind in at least 5 different scenes!

[embed]https://www.youtube.com/watch?v=yCLtNjbff-I[/embed]

This is the perfect movie if you love betting, Scorsese, and old-school Vegas.

2. Uncut Gems (2019)

[embed]https://www.youtube.com/watch?v=vTfJp2Ts9X8[/embed]

The fact that this movie didn’t get Adam Sandler his coveted Oscar is a true tragedy. One of the best movies of 2019, Uncut Gems follows Howard Ratner (Sandler), a jeweler and gambling fiend in New York City’s Diamond District, and his struggles to pay off massive debts through big bets and bigger gems. Sandler delivers a great performance. He stretches from his standard “normal guy who learns a heartwarming lesson and lands a girl way out of his league” role and creates an iconic character. We also see Kevin Garnett’s surprising acting chops. He plays the 2012 version of himself, an NBA star obsessed with Sandler’s rare black opal that he sees as a good luck charm.

Fair warning – this movie is INCREDIBLY frenetic, tense, and anxiety-producing. I’d recommend it for anyone who wants to see Sandler at his best and/or does not want to sleep for at least another 5 hours.

3. Eight Men Out (1988)

[embed]https://www.youtube.com/watch?v=JSHQw85pvek[/embed]

Eight Men Out tackles one of the biggest controversies in all of sports – the 1919 Black Sox, the eight members of the Chicago White Sox who worked with gamblers to illegally throw the World Series and were banned from the MLB for life. The movie illustrates the complexity of the situation and places blame on the owner Charles Comiskey, whose stinginess and unwillingness to reward his players lead them to find ways to make the money they felt they deserved. It’s certainly an interesting reminder that a hundred years ago, most athletes weren’t the millionaire superstars we see today.

Above all, Eight Men Out is perfect for fans of baseball, Charlie Sheen, and dudes chewing massive wads of tobacco in tiny hats. (There’s seriously so much chewing tobacco in this movie. It’s nuts.)

4. Two for the Money (2005)

[embed]https://www.youtube.com/watch?v=vcsdAwqZ-WI[/embed]

Not as well known, but this movie with Al Pacino and Matthew McConaughey is a fun, exciting movie about professional sharps and gambling consultants in the ‘90s. Its semi-autobiographical plot centers around Brandon Lang (McConaughey), a former college football player turned gambling oddsmaker, who’s plucked from his job as a telemarketer by Walter Abrams (Pacino), the head of a sports consulting firm. Abrams and Lang team up to create a TV show called The Sports Advisors (Abrams is based on Stu Feiner) which explodes in popularity as Lang’s picks hit at an insane rate (until they don’t.)

While it certainly didn’t win any awards, it’s an entertaining ride. (Of course, Pacino is incredibly outrageous and over the top!) And it's certainly an interesting take on life as a professional gambler. It’s also an inspiration to all of you rotting away in your office cubicle, hoping to make it big with your gambling smarts one day.

Also, for some reason, McConaughey insists on wearing sunglasses indoors for multiple scenes. This could not be more classic McConaughey.

5. The Gambler (1974)

[embed]https://www.youtube.com/watch?v=b-LdRzkWrDM[/embed]

To be clear, I’m talking about the James Caan (Sonny in The Godfather) version. Not the 2014 remake with Mark Wahlberg, which was a disappointment. The Gambler is an absolute classic and tells the story of Axel Free (Caan), a Harvard professor who throws away his perfect, cookie-cutter life with his increasingly-dangerous gambling addiction. After going down big to his bookie, Axel’s only way out is to convince his student, a star basketball player, to shave points off the upcoming game.

Caan plays a guy who steals from his own mother to feed his gambling addiction. The fact that he makes you care about his character is a testament to his acting ability. This is why he was nominated for the Golden Globe for Best Actor for his performance. Even 50+ years later, this movie holds up and is a must-watch for any gambler out there and one of the best sports gambling movies ever.