6 of the Best Movies About Betting

We all love a great drama where the protagonists lay it all out on the line. Even when they’re their own worst enemy. Nothing brings this all together better than a great flick about gambling. Usually a bit dark and with a seedy underbelly, you get to see the characters’ best and worst.

So, with that thought, let’s look at the top 6 movies about gambling (IMHO).

Rounders | 1998

Back in 1998, Rounders came out and was loaded with A-listers. Edward Norton, Matt Damon, and John Malkovich were all at the top of their Hollywood game. At the time, online poker was just getting underway, and underground poker rooms were becoming more popular. This film is about two friends caught up in the middle of mob-riddled, underground high-stakes poker. It wasn’t that popular when it came out, but the big poker boom in the 2000s made it a cult classic just a couple of years later. Some consider it a poker masterpiece, even if it is a little overly dramatic. In fact, you can learn more about the betting culture’s reality at sites like Sportsbook Review especially with the forum, is been active since the late ’90s. That said, some people speculate that the story is unofficially based on the life of Norm MacDonald.

Casino | 1995

Another 90s classic, Casino was a smash hit. Robert De Niro, Joe Pesci, Sharon Stone, and James Woods … directed by Martin Scorsese. Most people don’t realize that the screenplay for this epic mob and gambling magnum opus is based on Casino: Love and Honor in Las Vegas, a nonfiction title.

The film follows the main protagonist, Sam ‘Ace’ Rothstein, an expert sports handicapper who gets asked to head out to Vegas to run the Tangiers Casino (set up by the Teamsters). Teamsters, mob murders, FBI investigations, and memorable scenes like ‘the Cowboy Scene’ —among many others. Like Good Fellas, Casino is one of those films you can watch repeatedly, and it never gets old, even as the years fly by.

The Gambler | 2014

I mean … it’s right there in the title! John Goodman and Mark Wahlberg star in this film full of highs and lows. According to James Toback, it’s a remake of the 1974 film also titled, The Gambler, and the original screenplay is admittedly autobiographical.

White Men Can’t Jump | 1992

Woody Harrelson and Wesley Snipes play Billy Hoyle and Sidney Deane. A couple of pick-up game, streetball hustlers in LA. Ron Shelton directed the film, and although we’ll probably remember him most for Bull Durham, White Men Can’t Jump is an amazing flick. It’s not your typical sports betting or poker-type gambling film.

But a couple of hustlers who figure out a new way to game the crowds in parks around LA. Wesley Snipes shoots around, shows his skills, and talks a lot of trash, saying that he can be paired up with anyone and still win … even puts up 500 dollars, saying they can pick his teammate. Of course, they always choose the dopey looking white guy sitting on the bench with a dumb look on his face … he’s got handles and can shoot lights out … he just can’t dunk.

Gladiator | 1992

So, you probably thought I was going to be all card game movies and sportsbooks. But Gladiator is one of the best movies that you’ve never seen. Cuba Gooding Jr., James Marshall, and Brian Dennehy star in this underground boxing film where. Tommy (James Marshall) starts fighting in illegal underground boxing matches to get loan sharks off his dad’s back for his gambling debt. The film is great because it not so softly vilified boxing promoters, not so much the seedy underground betting scene.

Uncut Gems | 2019

Another unexpectedly fantastic movie. With Adam Sandler and Uncut Gems that arrived on Netflix, I feel like his attempts at drama can be hit or miss. This one was definitely hit. A jeweler who deals in a bit of shady business, but has starred for clients and a severe gambling problem, gets the inside track with the Boston Celtics by motivating Kevin Garnett. So, he takes a player prop parlay on the big guy to hit it big … but you’ll have to watch the movie to see what happens!