The 10 Best Casino Movies to Watch This Weekend

Thursday 13th July 2023
|In Addenda
|By Freelance Contributor
Photo: Mike Boening

In the mood for some high-stakes action, drama, and suspense this weekend?  Or maybe, with the rise in popularity of online social gaming (whether that’s specific websites like Chumba, game developers like Epic, and new platforms like the Metaverse), planning to get dressed up and host a casino-themed night with your favorite games ready? From classics to modern blockbusters and everything in between, there’s something for everyone on this list – even those who’ve never set foot in a casino before.

So go and grab some popcorn, and get ready to win big on entertainment with our list of the best casino movies to watch this weekend.

  1. Ocean’s Eleven (2001)

No casino movie list would be complete without mentioning the iconic Ocean’s Eleven. This heist film follows Danny Ocean (George Clooney) and his star-studded team of 11 expert thieves as they attempt to rob not just one, but three Las Vegas casinos at the same time. 

With an impressive cast including Hollywood favorites, Brad Pitt, Matt Damon, and Julia Roberts with their unsurprisingly witty interactions, Ocean’s Eleven is a must-watch for any fan of this – admittedly – very specific genre.

  1. Casino Royale (2006)

The James Bond franchise has always been associated with high-stakes gambling (and martinis – shaken not stirred), and Casino Royale takes this to a whole new level. Daniel Craig’s debut as 007 sees him as the suave and sophisticated secret agent as he takes on Le Chiffre (Mads Mikkelsen), a terrorist financier who uses a high-stakes poker game to launder his money. 

With intense action sequences, breathtaking scenery, and a touch of romance (of course), Casino Royale was everything we could have hoped for to start the new era.

  1. Rounders (1998)

Before there was Molly’s Game, there was Rounders. This classic poker movie follows the journey of Matt Damon’s Mike McDermott (see what they did there?), a law student and “reformed” gambler who gets back into the poker world to help a friend in need. With a recognizable supporting cast including Edward Norton and John Malkovich, Rounders is one to watch if you’re interested in learning the art of the bluff and an absolute must-watch for any poker enthusiast looking to up their game.

  1. The Sting (1973)

Set in the 1930s, following the glamor and debauchery of the Roaring 20s, The Sting is a classic caper film where small-time grifter Johnny Hooker (Robert Redford) teams up with veteran con man Henry Gondorff (Paul Newman) to take down a corrupt banker. The film’s classically intricate plot, stunning costume design, and seriously jazzy soundtrack all come together to make The Sting an unforgettable movie experience that would inspire many modern classics to come.

  1. Rain Man (1988)

While not strictly a casino movie, but worthy of this list all the same, Rain Man features one of the most memorable casino scenes in cinema history. Tom Cruise stars as Charlie Babbitt, a selfish and materialistic car dealer who discovers he has an autistic brother named Raymond (Dustin Hoffman) with an incredible talent for counting cards. Together, they embark on a road trip that takes them to Las Vegas and the blackjack tables, where Raymond’s skills help them win big. 

With exceptional performances from both Cruise and Hoffman, Rain Man is a heartwarming tale about brotherhood and the power of love. What more could you want?

  1. 21 (2008)

Based on the true story of the MIT Blackjack Team, 21 follows a group of brilliant students as they use their math skills to beat the casinos at their own game. Starring Jim Sturgess and Kevin Spacey, the movie explores just how far people will go to win big – you may be surprised. With a thrilling plot and slick production values, 21 is a must-watch for anyone who loves a good heist movie (or aspires to a life of counting cards).

  1. The Cooler (2003)

William H. Macy stars as Bernie Lootz, a professional loser who works for a Las Vegas casino as a “cooler” – someone whose bad luck rubs off on other players and helps the house win. However, things change when Bernie meets and falls in love with a cocktail waitress named Natalie (Maria Bello), and his luck starts to turn around. With great performances and a unique premise, The Cooler is a hidden gem in the casino movie genre and worth a watch if you haven’t already.

  1. Hard Eight (1996)

Written and directed by Paul Thomas Anderson, Hard Eight is a gripping character-focused movie that digs deep to explore the seedy underbelly of the casino world. The film follows John (John C. Reilly), a down-on-his-luck gambler who meets a mysterious older man named Sydney (Philip Baker Hall) who offers to teach him the ropes. As they navigate the high-stakes world of gambling, the lines between mentor and mentee become blurred. 

With a tense script, outstanding performances, and a killer soundtrack, Hard Eight is a must-watch for any fan of Paul Thomas Anderson or the casino movie genre.

  1. The Cincinnati Kid (1965)

Starring Steve McQueen and Edward G. Robinson, The Cincinnati Kid is a classic poker movie that has stood the test of time. McQueen stars as Eric “The Kid” Stoner, a young up-and-comer who takes on veteran card player Lancey Howard (Robinson) in a high-stakes game of poker. With stylish direction, sharp dialogue, and memorable performances from both leads, The Cincinnati Kid is a masterclass in the art of the bluff.

  1. Mississippi Grind (2015)

Mississippi Grind is your classic, modern-day road trip adventure. It follows Ryan Reynolds and Ben Mendelsohn as gamblers who travel down the Mississippi River in search of their next “big win”, forming an unlikely friendship along the way. With a moody atmosphere, stellar performances, and an authentic feel for the world of gambling, Mississippi Grind is a hidden gem that deserves more attention.

Watch a couple of these this weekend and who knows, you might even pick up a few tips.