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Must-See Top Gambling Movies

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Must-See Top Gambling Movies

Gambling movies run the gamut from cringeworthy to classic so let’s check out some of the best of all time and see if you agree.

Cincinnati Kid (1965) – In the ’60s, Steve McQueen was as cool as the other side of the pillow and in his breakout performance, he plays a Depression-Era local card shark named Eric Stoner who decides he wants to prove he can play with the best. This leads him to a high stakes game against Lancey “The Man” Howard played by the incomparable Edward G Robinson. Intrigue ensues when The Kid realizes that the fix is in – for him and against an unwitting Howard – but he wants to play it straight and win it fair. The final scene culminates in an all-in pot where the winner is…

Steve McQueen

Uncut Gems (2019) – Adam Sandler breaks his carefully constructed mold as a comedic character and seamlessly morphs into Howard Ratner, a Jewish jewelry dealer in New York’s Diamond District, with a taste for gems but an even bigger appetite for sports betting. Ratner gets a hold of a rare black opal from the mines of Ethiopia and realizes it is his ticket out of debt with his brother-in-law/loan shark to whom he owes $100,000.

Ratner is in an unhappy marriage and has a smokin’ sidepiece Julia, played by the aptly named Julia Fox, who is happy to ride the crazy wave of Ratner’s rollercoaster life as long as her sugar daddy keeps paying her bills. Ratner is eager to put the uncut gem up for auction where he believes it will fetch a cool million but things go sideways when Celtic’s great Kevin Garnett borrows the piece. Ratner spends days trying to retrieve it in order to get it to auction, sell the gem, make the money, and pay the debt. Garnett offered $175,000 for the good luck charm but Ratner rebuffs his offer while his loan shark’s thugs are chasing him all over town and roughing him up whenever they get the chance.

In a movie full of twists, it takes yet another few turns at the end. Sandler shows his range as an actor and proves he’s got some serious acting chops – you can bet on it.

Adam Sandler Uncut Gems
Photo by Tommaso Boddi/Getty Images/AFP

Rounders (1998) – The movie that set ablaze Texas Hold’em going mainstream has to be on anyone’s list of the best gambling movies of all time. Matt Damon is perfectly cast as Mike McDermott, a law school poker savant with a penchant for reading his opponents and winning underground games. But his big, wide smile could not shake him free from the clutches of Russian mobster Teddy “KGB”, played sublimely by the immaculate John Malkovich, to whom he lost 30 large and vowed to his girlfriend he would quit playing poker and focus on his studies.

Well, that wouldn’t make much of a movie so another pair of characters, Joey Knish and Lester “Worm” Murphy, played by John Turturro and Ed Norton, respectively, are poker pals of McDermott with vastly different perspectives on how to grind out a living around the felt. Knish is McDermott’s surrogate older brother, and mentor, while Worm is just a train wreck waiting to find an accident.

If the phrase, “Pay that man his money” doesn’t resonate with you then you haven’t seen this movie. Rounders boasts a truly magnificent cast and is worth watching over and over and over again.

Casino (1995) – This is another cinematic classic that belongs in the rarified air of the best gambling movies of all time. It’s in the gangster genre and sits alongside the likes of A Bronx Tale, Goodfellas, and The Godfather. Yeah, it’s that good and whenever Martin Scorsese and Robert DeNiro get together, magic happens. This collaboration also includes Sharon Stone, James Woods, and of course, the irresistible force that is Joe Pesci.

The movie is loosely based on the life of Frank “Lefty” Rosenthal, a sports handicapper turned Vegas sportsbook manager. The title character is Rosenthal Sam “Ace” Rothstein, played to perfection by DeNiro, and he is tasked with running the Tangiers Casino (based on the Stardust) for the Chicago mob. Joe Pesci renders a tour de force performance as Nicholas “Nicky” Santoro, a made man and enforcer of the Windy City syndicate but also a close friend of Rothstein.

The glitz, glamour, and opulence of Sin City, circa 1970’s, is on display amidst the backdrop of a gritty and grimy underbelly chock-full of greed, deception, and violence. Casino has everything you would expect from a Scorsese/DeNiro collaboration and the movie steals your attention from the opening scene to the final credits.

Deniro Casino

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