The Best Movies About Gambling

The world of casinos and gambling has long been a fascination of many storytellers working in Hollywood over the years. The list of movies, good and bad, that are set in this industry is long and quite varied. It must be something to do with the thrill of the stakes – winning or losing.

The Cooler

There’s something kind of cool about this unusual movie. William H. Macy plays a character who is incredibly unlucky and his lack of luck tends to rub off on people around him. The casino he works for sends him over to the tables where players are winning big, and Macy’s character essentially cools the table and stops the winning streak.

The film revolves around the concept of luck and all the superstitions that are so popular in gambling lore. It’s also an incredibly brilliant yet understated performance by Macy.


This is a Martin Scorsese classic, starring Robert De Niro and Sharon Stone at their best. As with all Scorsese films, this one is well researched and portrays a gritty reality of a mob-run casino in Las Vegas. The story looks at the evolution of the Las Vegas strip, and how it went from somewhere full of crime and not for everyday folk to the sanitized place of sin that everyone goes to for a good time. However, the gang influence has not been lost in Vegas.


It’s a fairly classic story of someone who hopes to use gambling as a way to get out of debt and get a leg up on a fiscally unfair world. Matt Damon plays a university graduate who believes he can win enough through playing poker to pay off his student loans. This film is very popular because it has such a truthful portrayal of what it’s like in a high-stakes poker game – the strategies used and the type of banter that’s typical from players.

It also features a pretty big cast in terms of big Hollywood names. These include Edward Norton and John Malkovich – two heavy hitters in terms of great actors.

Ocean’s 11

This film certainly does a lot to glamorize the world of casinos and thieves. However, it is a lot of fun and there’s nothing quite like a good caper film when you just want to be entertained. The all-star cast of excellent actors helps things too and the settings are as glam an online casino in Dubai.

The Cincinnati Kid

The oldest on the list, premiering back in 1965, The Cincinnati Kid is an absolute classic in the gambling film sector. It stars Steve McQueen as the titular character, an arrogant young poker player who is trying to hustle everyone he comes up against. The movie still holds up today as a great story with some superb acting performances.

The story follows the upcoming Kid and his path to facing off against the biggest name in the poker world for the day. McQueen’s character is a good player who has made a name for himself in the back rooms, but he’s cocky and could lose his one chance to make it big.