The 20 Best Gambling Movies to Watch if You’re Feeling Lucky – Men’s Health

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The allure of gambling is unmistakable. A little luck can change your life as quickly as a queen of diamonds landing next to an ace of spades and a jack of hearts in a blackjack game. Humans were gambling on horses before they were riding in cars. You’ve probably had to fight back FOMO after seeing someone on you Instagram feed turn a $.10 10-team parlay into your yearly salary. This innate desire to change your life is probably why the best gambling movies focus more on the humans gambling than the gambling itself.

Yes, films like The Safdie Brothers’ Uncut Gems feature a series of huge sports bets. But, it’s Adam Sandler’s picture-perfect of the emotional instability of gambling addict Howard Ratner that makes that gives the gambling existential stakes far beyond a huge payday. The movie 21 highlights the thrill of manufacturing luck with ingenuity and skill in a way anyone whose bank account has been at the mercy of Las Vegas casinos. But, at its heart, the movie explores the inability to walk away from a sure thing that makes a movie anyone who believes in luck. We love gambling films because they show us the type of people we can become if we givehttps://www.menshealth.com/ent… into our greediest impulses.

If you’re feeling lucky and want to see what that luck can get you, put down the FanDuel app and check out the 20 best gambling movies you can watch to satisfy your hunger for more.

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Wake In Fright (1971)

In Australia, losing all your money gambling leads to drinking binges and fighting kangaroos, or at least it does in the eccentric psychological thriller Wake In Fright. Gary Bond, who looks like he and Robert Redford were separated at birth, is a teacher desperate to pay off his debt to the government and leave his job, gets intoxicated by a gambling winning streak in a weird town known as The Yabba, and ends up losing all the money he has, leading him on one of the most sinisterly trippy rabbit holes ever in a gambling-related film.

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Uncut Gems (2019)

Even if the most gambling you’ve ever done is using your social security number to play the lottery, directors Joshua Safdie and Benjamin Safdie mirror the emotional instability of a degenerate gambler visceral enough for you to feel a bit manic and paranoid while watching Uncut Gems. Jeweler Howard Ratner, played immaculately by Adam Sandler, will gamble anything away to crawl out of a never-ending debt spiral, including Boston Celtics Hall of Famer Kevin Garnett’s 2008 NBA Championship and mobster money. The film is an uncompromising look into how much gambling is truly a disease that can destroy a gambler’s life and the lives of nearly anyone who touches him. The lasting phrase from the film may be a delusionally confident Howard exclaiming, “This is how I win,” but the tragic irony of it all, gambling is ultimately how he loses everything.

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Ocean’s Eleven (2001)

Ocean’s Eleven isn’t just one of the greatest gambling movies, it could appear on lists for the best heist movies, best George Clooney movies, best movies from Las Vegas, and even best movies snubbed by the Academy Awards. Even though the film centers around internationally recognized thief Danny Ocean (George Clooney) rounding up ten criminal specialists to rob $150,000,000 from the Bellagio, the Mirage, and the MGM Grand casinos, the film is an exquisite look at how gambling in Las Vegas is more than Blackjack and rolling dice. Ocean gambles his freedom to win back his ex-wife Tess Ocean (Julia Roberts), casino magnate Terry Benedict gambles Tess like a poker chip to get back the money stolen from his casinos, and Ocean’s eleven gamble their lives for a sweet payday. In gambling, the house always wins until the perfect hand comes along. Ocean’s Eleven shows how sometimes you have to make your own luck.

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Killing Them Softly (2012)

The Great Recession of 2008 made many people take desperate measures to get money and Killing Them Softly punches you in the mouth with the harsh truth that robbing a mafia poker game isn’t the way to go. Brad Pitt and the late James Gandolfini briefly team up as Jackie and Mickey, two hitmen tasked with exacting some street justice on three men who perpetrated the robbery. Pitt ends up getting the jobs done himself like an angel of death befallen anyone silly enough to gamble their lives away by messing with the mafia.

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Geniuses from the Massachusetts Institute of Technology (MIT) can usually go on to do anything, yet a group of them decided to use their gifts to count cards. Based on the true story of an MIT Blackjack Team that went around the world using math to beat casinos at blackjack, the 2008 film puts the corruptive nature of gambling on the silver screen as Ben Campbell (Jim Sturgess) goes from gambling just to pay off his $300,000 tuition to being addicted to the rush of using his intelligence to become wealthy. He gets robbed at gunpoint, loses friends, and has very little to show for it besides a cool story. Watching the smartest people do the dumbest things could be enough to scare anyone away from gambling because winning is always enough until you want more.

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The Killing of a Chinese Bookie (1976)

In The Killing of a Chinese Bookie, gambling addict and strip club owner Cosmo Vittelli (Ben Gazzara), who fell back down a $23,000 poker debt hole just as he paid off a seven-year gambling debt, is forced to murder a bookie named Benny Wu to delete his gambling debt. And that’s just the beginning of his problems. For a thrilling two hours, The Killing of a Chinese Bookie begs the ominous question: How far will you go to get out of debt?

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Molly’s Game (2017)

Gambling is typically portrayed in films as a boys’ club, but Aaron Sorkin’s Molly’s Game shows how women can be even more adept at navigating the treacherous world of underground gambling. Molly Bloom (Jessica Chastain) uses her wits and charm to go from Olympic-level skier to assistant at one underground poker game to the owner of her own underground poker game, all while rubbing shoulders with celebrities, wealthy professionals, and Russian mobsters (They seem to be in every gambling film). As with the best gambling movies, the poker table is only one arena where the stakes are high in Molly’s Game. She relies on gambling the people’s identities from her poker game to keep her money and avoid prison when the FBI comes knocking. The scenes between Chastain and Molly’s lawyer Charlie Jaffey, played by Idris Elba, are enough to make this movie worthwhile, but Molly’s Game truly adds a unique twist on how disparate lives can all become perilously connected on a poker table.

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Lock, Stock, and Two Smoking Barrels (1998)

The reason you know director Guy Ritchie and Jason Statham traces back to Lock, Stock, and Two Smoking Barrels, a dark comedy that is one part heist film, one part gambling film, and two parts hijinks. After losing £500,000 in a rigged card game, friends Bacon (Jason Statham), Tom (Jason Flemyng), Eddie (Nick Moran), and Soap (Dexter Fletcher) engage in a series of capers to pay back their debts, including robbing cannabis growers, narrowly escaping an ambush, somehow escaping arrest. As a gambling film, Lock, Stock, and Two Smoking Barrels succeeds at finding the humor in people trying to cheat their way into money, only to twist their lives around to wiggle their way out of debt.

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Casino (1995)

How did Las Vegas become the epicenter of all things gambling? You could read up on the seedy history of Sin City, or you could spend close to three hours watching a Martin Scorcese masterpiece. Sam “Ace” Rothstein (Robert DeNiro) unofficially runs the Tangiers Casino in Las Vegas at the direction of the Chicago Mafia and acts as the viewers’ eyes and ears to the unseen machinations of running a casino in Las Vegas. The payoffs to the mafia, the politicized wranglings with the Nevada Gaming Board, the berated Blackjack dealers, and the showgirls are explored like parts of the blueprints of the Vegas gambling world. Casino is one of Scorcese’s epic American tragedies exposing the human core of the gambling illusion to unparalleled effect in terms of scope and story. Rothstein comparing running a casino to “selling people dreams for cash” is one of the most concise ways of encapsulating all that gambling is to the world.

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Rounders (1998)

There was a glorious point in the ‘90s when Matt Damon seemed only to play unassuming boy genius to his degenerate friends, and Rounders is arguably his finest portrayal of the golden boy archetype. Mike McDermott (Damon) is a poker prodigy whose dreams of playing in the World Series of Poker are destroyed after he loses $30,000 in one hand of poker, only for them to be rekindled by his desire to help his hustler friend Worm (Edward Norton) pay back his debt to a pimp and a frightening Russian mobster Teddy “KGB” (John Malkovich). The typical gambling tropes (mobsters and a crushing debt catalyst) are present. Still, there’s a cerebral element to the filmmaking that makes Rounders awe-inspiring even to someone who only thinks the river is a body of water. McDermott sees inside the mind (and hand) of a diabolically stoic Russian mobster by watching how he eats Oreos. That’s enough to put Rounders on the shortest of shortlists of best gambling movies ever.

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Win It All (2017)

The worst gambling addicts are the ones who seem to be addicted to losing yet always think they have a shot at winning, and Eddie Garrett (Jake Johnson) in Netflix’s original comedy film Win It All fits that bill perfectly. Eddie is on the road to gambling recovery thanks to his addiction recovery sponsor Gene (Keegan-Michael Key) until Eddie is tasked by a thug named Michael (Jose A. Garcia) to store a duffle bag full of money of his while he is away in prison in exchange for $10,000. Eddie stupidly begins gambling the money in the bag and is somehow saved from himself in the end thanks to a small heart attack. Outside of Eddie’s hilarious misfortune and idiotic gambling logic, Win It All actually has an empathetic core and is a great advertisement for the benefits of addiction counseling.

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The Card Counter (2021)

Few gambling movies portray gambling less as a talent and more as a coping mechanism, like Paul Schrader’s 2021 crime drama The Card Counter. Oscar Issac plays card counting wizard William Tell who teaches himself how to count cards in a military prison to practice the patience and restraint from succumbing to the darker impulses that landed him in prison in the first place. Throughout the film, this control of one’s decisions central to gambling is what he tries to instill in a Cirk Baufort (Tye Sheridan) seeking to avenge his father’s death lethally. When films like The Card Counter uncover the psychological connection between being good at gambling and dealing with being a human, they create something truly magical that stands the test of time.

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The Gambler (1974)

Gambling hasn’t lost its cultural vitality over decades, and the same is true for great gambling films like 1974’s The Gambler. James Cann as gambling addict Axel Freed is obsessed with the thrill of gambling, even if it ends in self-destructive losses, and director Karel Reisz depicts the downward spiral of addiction with depressing accuracy. Freed gambles with more than his and other people’s money; he gambles with his life, putting himself in dangerous situations for his sadistic enjoyment. Besides a stellar cast including The Goodfellas’ Paul Sorvino and American Gigolo’s Lauren Hutton, The Gambler is a psychological thriller masked as a gambling movie.

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Lucky Number Slevin (2006)

Trying to keep up with all of the twists in Lucky Number Slevin is almost as difficult as picking a winner in a horse race but just as entertaining. In the crime noir film, Slevin Kelevra (Josh Hartnett) is forced by a mob boss and a rabbi to pay a large gambling debt after being mistaken for his friend Nick Fisher (Sam Jaeger) before turning the tables and revealing his murderous revenge plot that will leave your jaw on the floor. Bruce Willis plays a hitman with the occasional heart of gold, Mr. Goodkat, with a steely temerity that adds a jagged cherry on top of this cinematic delicacy that uses the generational ramifications of gambling debt to tell a unique father-son revenge story seldom seen in gambling flicks.

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The Color of Money (1986)

No scientific studies have proven if Tom Cruise in the ‘80s could make anything cooler. Still, if there were, the magnetic bravado he brought to pool hustlers in the 1986 film The Color of Money would be all the evidence you need of his infectious coolness. Playing hotshot Vincent Lauria in the sequel to 1961’s The Hustler, Cruise joins a pool hustling crew with his girlfriend Carmen (Mary Elizabeth Mastrantonio) and Eddie ‘Fast Eddie’ Felson (Paul Newman) from the original Hustler film to terrorize pool halls with no-look corner pocket shots and nunchuck pool stick swinging like a gambling ninja. There’s betrayal, enraptured Martin Scorsese directing, and enough banter between Newman and Cruise to make this a must-see classic, gambling or not.

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Hard Eight (1996)

The 1996 film Hard Eight is a must-watch based on the cast alone. Philip Baker Hall plays surly gambling pro Sydney; Gweneth Paltrow plays waitress/prostitute Clementine; John C. Reilly plays gullible loser John Finnegan; Samuel L Jackson plays slick-talking, no-nonsense casino security personnel Jimmy. For a little over 90 minutes, Hard Eight Sydney takes John under his gambling wing after helping his homeless protege get enough money for his mother’s funeral. After John falls for Clementine, it sets in motion a series of events that involve a dead tourist, a honeymoon that doubles as a getaway excuse, and a father-son twist that makes Sydney’s relationship with John a bigger gamble than any game of Blackjack they play.

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Even Money (2006)

Gambling unites people in a shared desire (usually desperation) to reverse their bad luck, and in the underrated film Even Money, three strangers’ lives intersect through their gambling addictions in a complex manner. Kim Basinger, Danny Devito, and Forest Whitaker play the three central characters Carolyn Carver, Walter, and Clyd Snow, respectively, while supported by an embarrassment of riches in co-stars including Tim Roth, Ray Liotta, Kelsey Grammar, and Jay Mohr. Even Money has everything you need in a great gambling film: a rigged college basketball game, an addict gambling away their connection to their family, and mob bosses ready to break ankles at any moment to get their money back. Do yourself a favor and check out this rare gem in the pantheon of great gambling flicks.

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Dark City (1950)

The charm of the 1950 crime noir film Dark City is how quickly a movie about gambling can turn into a murder mystery revenge flick. In his Hollywood debut, Charlton Heston plays Danny Haley, the owner of an illegal gambling operation who turns into a detective after one of the patrons of his establishment commits suicide and has a brother hellbent on avenging his death. Somehow director William Dieterle fits a romantic ending into a gambling film where lives are lost just as easily as money is.

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White Men Can’t Jump (1992)

White Men Can’t Jump is centered around two basketball hustlers, Sidney “Syd” Deane (Wesley Snipes) and Billy Hoyle (Woody Harrelson)— who would gamble their last breath on making a jump shot if it meant they could gamble their next one. Billy makes a living lulling people into a false sense of confidence on the court because of him being an unassuming white man before turning into Larry Bird and snatching the money he can. Teaming up with Syd, someone equally adept in blacktop trickery, Billy loses it all, then wins it all, then loses it all again, and then wins it all back but ultimately loses what matters most, his girlfriend Gloria Clemente (Rosie Perez) after he chose to gamble her money over getting an honest job. What makes White Men Can’t Jump is how it displays the almost imperceptible difference between betting on yourself and betting for yourself. Gloria trained to compete on Jeopardy! Because she was confident in betting on her preparation and smarts because it was a dream of hers. Billy made bets because his identity is inextricable from his gambling addiction.

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The Sting (1973)

There is a thin line between a con-man and a gambler, and the Best Picture-winning The Sting is one of the best films in both genres. Paul Newman as con-man Henry “Shaw” Gondorff and Robert Redford as grifter Johnny “Kelly” Hooker join forces in a long con against crime boss Doyle Lonnegan so intricate, it turns into a con within a con within a con no one watching for the first time can predict. From a phony off-track betting parlor and waitresses doubling as assassins to fake FBI agents and real murder, The Sting is the benchmark of great gambling movies.

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