Bruce Dias 
There has always been something special about watching people take chances on the roll of a dice, the turn of a card, or the first to cross the finish line on the big screen. Gambling, betting, and casino lights feel like they were made for Hollywood. The biggest stars, the best directors, and watching iconic characters risk it all; there really is nothing like it. No matter what kind of movies you tend to prefer, most people tend to agree that watching a great cast of characters pitting their wits against each other, the big casino, or the odds is always going to be a good time.
If you are looking for some inspiration for an upcoming movie night, or if you want some music, style, or drink tips for planning a casino night at home, here are some of the coolest movies about gambling, gamblers, and casinos for you to choose from.
The Hustler (1959)
There are very few classic screen icons that can lay a claim to “King of Cool” as decisively as Paul Newman in his heyday. In this legendary movie, the former Butch Cassidy plays Fast Eddie Felson, an upcoming young pool hustler who is trying to break into the big leagues. At the top of those leagues is Minnesota Fats, played by Jackie Gleason. The movie shows the ups and downs (including some nasty broken thumbs), but Newman is magnetic throughout. He would later reprise the role in Martin Scorsese’s The Color of Money in 1986, where his character teaches Tom Cruise’s Vincent about the risks and rewards of hustling. The sequel is good, but the original is better.
Ocean’s Eleven (2001)
If Paul Newman was one of the coolest men alive in the 1960s, then the 2000s were all about George Clooney and Brad Pitt. Steven Soderbergh’s remake of the Rat Pack movie amps up the style and swagger to incredible heights, making for a classic caper that you can watch again and again. Danny Ocean and his team are not just here to take one casino; they’re here to take three.
The glitz and glamor of Las Vegas have never seemed more appealing, and if you are looking for some inspiration for an at-home casino night, then this could be the best choice. And if Vegas is a little too far to go for casino games, then why not invite some friends over for some online poker action? With online casinos, you can play a wide range of different games without the hassle of heading to a brick-and-mortar location. Visit PlayLive to check out the incredible range of different options and enjoy some big bonuses.
Rounders
This movie has a very special place in the heart of anyone who was a teenager in the late nineties and early noughties, thanks to the chemistry between stars Matt Damon and Edward Norton, who were both in the midst of becoming major stars at the time. Damon plays Mike, a law student who loses big at the start of the film and pledges to leave poker behind him. But when his old friend Worm gets out of prison and has a big debt to pay off, Mike finds himself back at the table against his better judgment. The poker scenes in the movie have been consistently praised for their accuracy, and it is incredibly tense stuff watching Mike risk it all against John Malkovich’s Russian crook.
Croupier
British director Mike Hodges may be best known for the Michael Caine classic Get Carter, but he enjoyed a resurgence in 1998 with his low-key modern classic Croupier. Clive Owen stars in a break-out role as a novelist who takes a job as a croupier. The more time he spends in this environment, the more appealing it becomes, and before too long, he is getting roped into a casino heist.
Of course, things do not go as smoothly as they had planned. Croupier is not as well-known as some of the other films on this list, but it got a lot of love following Hodges’ recent passing and has always enjoyed a great reputation among fans and critics. If you want some cool British textbooks, you need to seek this one out.
California Split
The great Robert Altman directed this low-key story about two gamblers who become buddies and embark on a series of attempts to win big. Elliot Gould is the more confident of the two, while George Segal is the one who could use a little guidance. While the vibes of this film may not immediately scream cool, there is something incredibly stylish about the hang-out vibes of this story of two friends supporting each other and beating the odds. The film was loosely remade in 2015 with Ryan Reynolds and Ben Mendelsohn in the lead roles, and it’s definitely worth a look too.
