The Top 10 Classic Gambling Movies of all-time

Top 10 Gambling Movies of all Time

Not everyone is going to agree with the choices we’ve made in our Top 10 classic gambling movies of all time. Some of our choices are considered critical masterpieces. Some of our choices are definitely cult viewing only. Whatever your opinion, be sure to check out some of these greatest gambling movie titles for inspiration before your next visit to your favourite online casino for a Video Poker, online slots or Live Video Dealer Blackjack session.

1. Casino

Arguably, Casino is the most famous of all gambling movies and a sweeping classic that sits comfortably on most critics’ Top Ten All Time Favourites lists, Casino is the epic and sometimes violent tale of mob-controlled casino gambling in Vegas. Robert De Niro and Joe Pesci are the stars, the first as a casino owner with mafia ties and the latter as his sociopathic enforcer whose increasingly wild and erratic behaviour begins to unravel their casino empire. Sharon Stone adds her seductive charms to the stellar cast. Throw in Martin Scorsese’s direction and some of the most harrowing and memorable scenes in cinematic history and the result is movie perfection.

2. Lock, Stock & Two Smoking Barrels

Possibly the greatest British comedy of all time. The plot of Guy Ritchie’s classic tale involves four knockabout East London lads trying to cheat a gangster by counting cards to win a fortune only for the gangster to cheat them straight back. The lads must then come up with 500 000 pounds to pay him back before he kills them. Loaded with a killer soundtrack, quintessential English gags. East London cockney rhyming slang and a fun cast including Jason Statham, Sting and ex-hard man footballer Vinnie Jones, this movie is an absolute hoot and will have you in stitches from start-to-finish.

3. Rounders

Featuring a young Matt Damon, Rounders is the story of an entrepreneurial young man who is trying to pay his university fees by winning it at the poker table. Full of famous actors, the movie also stars John Malkovich and Edward Norton. The movie culminates in a dizzyingly high stakes game, with Malkovich playing a wild-eyed poker baron that Damon must try and defeat. The movie features brilliant performances from its cast and Norton, in particular, is spectacularly good. Watch out for the realistic depictions of poker strategy and table banter that few other gambling movies manage to pull-off as successfully as Rounders.

4. The Sting

Paul Newman and Robert Redford, who combined so successfully over the course of their careers – play two con men, one a beginner and the other a professional. Together, they target a high-flying, gambling-loving criminal boss who is tracking down Redford’s character from a previous swindle. Full of as many twists and turns as you can possibly imagine, the ‘long con’ gets ever-more complicated as does the danger levels for both protagonists as the movie reaches a dramatic finale. The Sting is a high-quality, nail-biting, suspense-filled thriller.

5. 21

The real story of a group of genius MIT students is one of my favourites. This cinema gem stars Jim Sturgess as the bright young student who is the wunderkind of the student group and Kevin Spacey as the maths professor who trains the group to count cards on the Vegas strip and earn millions as a result. What ensues is a thrilling tale of casino gambling, Blackjack card counting, twisting trickery, betrayal and hedonism that seems way too outrageous, if it hadn’t actually happened for real.

6. The Hustler

A young Paul Newman plays Fast Eddie Felson, a talented, yet cocky pool shark going ‘all-in’ against Minnesota Fats (Jackie Gleason), the best player in the business. After a hot start, Eddie’s pride gets in his way and the game continues for a marathon 25 hours. Unable to hold his alcohol, Eddie loses his world and hits absolute rock bottom. After confiding in Sarah, a tortured alcoholic, Eddie picks himself together to try to beat Fats once and for all. Paul Newman owns this classic film in an astonishing performance.

7. The Cooler

William H. Macy plays Bernie Loots, the professional loser (‘cooler’) of the title – a man whose luck is so bad that casinos employ him to restore their house edge by standing nearby punters on hot streaks. Without fail, their luck always changes bad. However, when the cooler’s own fortunes change after a fling with a waitress, he suddenly finds himself being the lucky charm of every gambler in Vegas – much to the annoyance of the casinos that employ him. Macy delivers a superb central performance. The Cooler is a whimsical look into the roles of fate, luck and superstition in gambling.

8. Owning Mahowny

Philip Seymour Hoffman plays Dan Mahowny, a Toronto bank manager who seems like a fully-invested boring professional, focused on being frugal. What transcends and plays out is the true story of the largest bank-fraud case in Canadian history. In his position, Mahowny has access to a multimillion dollar account, ultimately leading him to lose CAD$10 million in 18 months. Hoffmann’s brilliant performance portrays Mahowny’s obsession with the process of losing total control, rather than the thrill of the win.

9. Casino Royale

Ian Fleming’s story stars Daniel Craig, as James Bond, 007. Set at a breakneck speed, the story follows Bond as he takes on the obligatory villain, the Poker-playing, torture-inflicting, Le Chiffre. The most memorable scene in the movie centres on an incredible showdown in the Monte Carlo when Bond takes on his adversary in an all-or-nothing high stakes Poker game. The pace is furious, co-star Eva Green is stunning and the poker play is simply the best.

10. Ocean’s Eleven

Steven Soderbergh’s highly-stylised heist drama tells the story of a group of eleven people who are looking to rob three Las Vegas casinos. The film is a higlyly entertaining romp. It’s difficult to ignore the gambling undertones shaping the outcome of this tale. The whole heist plan itself has a gigantic house edge, even if they manage to pull it off successfully. A remake of the 1960 film of the same name, Soderbergh’s version edges out the original with the flamboyant interplay between George Clooney and Brad Pitt and the slick and clinical execution.