These are the 25 best movies about gambling, according to griersonleitch
California Split. Photo: Courtesy of Columbia Pictures Movies about gambling have an inherent drama because, by definition, they’re about risk. It’s not fun to watch someone be prudent and cautious, but to see someone constantly putting his well-being on the line in desperate, irrational hope for that One Big Score … well, gamblers in gambling movies are in many ways just like that veteran cop who takes One Last Case before retirement.
23. 21 Based on the true story of the MIT Blackjack Team that beat the house for nearly a decade, 21 turns an interesting math and business story into a sort of dumb heist movie featuring a lot of young, handsome actors trying to pull one over on Kevin Spacey. Spacey is particularly checked-out here, and the movie was criticized for “whitewashing” in its casting, turning the mostly Asian-American real-life players into generic white people.
19. Ocean’s Eleven Often, movie characters who gamble are presented as sobering cautionary tales. Nobody told Steven Soderbergh, who turned his remake of the creaky Rat Pack caper into a jazzy, fleet-footed blast. From the early scene where George Clooney and Brad Pitt’s ultra-cool characters square off at the card table, it’s clear that this Ocean’s Eleven will exude the sleek, cocky spirit of modern Vegas, which is all upscale adult pleasures and very little actual degenerate behavior.
15. Bugsy An origin story of Las Vegas, Bugsy is principally a study of Bugsy Siegel, a gangster who travels to the desert, convinced he’s seen the mob’s future. Lavish, classy, and smart, director Barry Levinson’s Oscar-winning drama follows Siegel in his seemingly quixotic dream of creating a mecca of gambling and casinos, and Warren Beatty keenly plays him as a man of passions but perhaps not enough reason.
11. The Sting Who says gambling can’t be really fun? This Best Picture winner exudes pure pleasure … well, unless you run afoul of Shaw and Kelly , that is. These two con men decide to take down a no-good mobster , and their elaborate grift involves card games and horse racing. Understanding the machinations of Shaw and Kelly’s plan doesn’t matter — it’s just a delight to watch the characters turn The Sting into one big, electric narrative sport. These are some winners who are easy to root for.
7. Croupier Clive Owen has been such a familiar, somewhat disappointing, presence in films for the last two decades that it’s now hard to remember what a lightning bolt his arrival was. So go back and rewatch Croupier, where all that promise was laid out fairly magnificently. He’s Jack, an aspiring novelist desperate for money — soon, he’s a croupier getting to know the world of casino gambling.
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