This Is How They Win: 7 Gambling Movies To Watch After You Check Out Uncut Gems

The gambling movie is one that can be tense, suspenseful, tragic, funny, ridiculous and heart breaking all at the same time. Most people have had a day dream of hitting it big and that’s something they all have in common with the characters in all these films. Below are eight gambling movies you HAVE to watch if you haven’t already.

Uncut Gems

The Safdie Brothers newest film tells the story of the ultimate deadbeat, scumbag, in over his head, piece of garbage gambler who’s played by Adam Sandler. You’re going to hate him throughout the film for every terrible choice he makes. Over and over and over again. Below is his first interaction with Kevin Garnett, who plays himself, and the Opal with dubious magical powers:

The Gambler

The Gambler stars James Cann in what turns out to be a stomach turning character study into how a degenerate gambler thinks and acts. Cann has a serious gambling problem and he doesn’t focus on just one game – he just wants to gamble and winning doesn’t really matter.

Hard Eight

This was Paul Thomas Anderson’s first film starring Philip Baker Hall and John C. Reilly about a pair of gamblers in Reno. Craps is there game and it features Phillip Seymour Hoffman in a tiny roll as an amazing obnoxious craps player at the table.


Rounders, starring Matt Damon, Ed Norton and John Malkovich delves into the world of illegal Texas Hold ‘Em poker games around New York City. Ed Norton is Damon’s scumbag degenerate buddy who hustles games around the city. Damon’s final poker game against John Malkovich is one of the most tense on screen moments in a gambling movie.

Bad Lieutenant

Harvey Keitel is the Bad Lieutenant, a coke snorting, dope shooting crooked NYC cop. One of the throughlines of the film is his bad bets on a fictitious 1992 NLCS series between the Mets and Dodgers. Spoiler alert – his gambling on the games is what ultimately does him in. Probably deservedly so.


James Woods and Oliver Platt play a pair of con men who try to hustle Bruce Dern, who runs a small boxing town. Yes, a town centered around boxing. Who doesn’t want to see James Wood be a sleazeball? It’s a great boxing, AND great gambling flick.


Let It Ride

Richard Dreyfuss is a down on his luck track rat who gets a hot tip and lets it ride all day long. David Johansen is his dirtbag buddy, Teri Garr is his wife and the movie also features an an incredibly attractive Jennifer Tilly. This movie is the fantasy every horse racing bettor has had rolling around in their head their whole lives.

Two For The Money

is this the best movie on the list? No. But it’s still a fun sports gambling movie. Matthew McConaughey is a former football player who handicaps games incredibly well and he goes to work for an overacting Al Pacino. It’s less dark than some of the other films on the list but it was also based on a true story about Brandon Lane who was a former college football player turned incredibly successful handicapper.

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