There is something irresistible about the thrill of the casino. You’re lucky if you’re a fan of playing blackjack at sites like Betshah.com, and the queen of diamonds is dealt to the spot between the ace of spades and the jack of hearts. Bets were being placed on horses by humans even before automobiles were commonplace. You’ve had regretful envy after seeing someone on Instagram win a 10-team parlay for $.10 and walk away with a paycheck that could support your family for a year.
The best gambling movies, I imagine, are about the people playing rather than the gambling itself because of the universal human yearning to make a fresh start.
Several large wagers on sporting events are featured in movies like Uncut Gems by the Safdie Brothers. But it’s Adam Sandler’s pitch-perfect portrayal of Howard Ratner’s emotional instability at the tables that makes gambling about more than just making a lot of money.
As anyone whose bankroll has been at the mercy of Las Vegas casinos can attest, there is nothing quite like the rush of creating your luck via ingenuity and talent, and the sensation is amplified in the film 21. To those who believe in luck, however, the movie’s central theme is the difficulty of turning away from a definite thing.
When you’ve had enough of the FanDuel app and want to see what else the luck of the draw can get you, here are the top 7 gambling movies to watch.
In the bizarre Australian psychological thriller Wake in Fright, a man loses all his money gambling, then binge drinking and fights kangaroos. A teacher named Gary Bond (played by an actor who looks like he and Robert Redford were separated at birth) is desperate to pay off his debt to the government and leave his job when he gets drunk on a winning gambling streak in a strange town called The Yabba and promptly loses everything, sending him down one of the most sinisterly trippy rabbit holes ever seen in a film about gambling.
Suppose your only experience with gambling is using your SSN to buy lottery tickets. In that case, directors Joshua Safdie and Benjamin Safdie nevertheless make you feel a little bit frantic and worried by accurately portraying the emotional instability of a degenerate gambler in their film Uncut Gems.
Adam Sandler’s Howard Ratner, a jeweler mired in poverty, will gamble away anything—including the 2008 NBA Championship won by Kevin Garnett and the money he stole from the mob—in an attempt to escape his crushing debt. The film provides an unflinching look at how gambling can ruin not just the gambler’s life but also the lives of those closest to him. Gambling is the sad irony that causes Howard to lose everything, and the phrase “This is how I win” may be the most memorable line from the film.
In addition to being one of the finest gambling movies, Ocean’s Eleven also deserves to be on lists of the best heist movies, the best George Clooney movies, the best movies set in Las Vegas, and even the best movies that were overlooked by the Academy Awards.
Even though world-famous burglar Danny Ocean (George Clooney) organizes a team of ten criminal specialists to rob $150,000,000 from the Bellagio, the Mirage, and the MGM Grand casinos, the film offers an amazing look at how gambling in Las Vegas is so much more than just Blackjack and rolling dice.
To win back his ex-wife Tess, Ocean risks his freedom, casino magnate Terry Benedict risks Tess like a poker chip to recover the stolen funds from his casinos, and Ocean’s Eleven risks their lives to make a quick buck. The house always wins in gambling until the player gets a royal flush. In Ocean’s Eleven, we see that luck can be created.
Killing Them Softly is a gut punch of a book that tells you that robbing a mafia poker game isn’t the method to obtain money, even though many people did so during the Great Recession of 2008.
For a short while, Brad Pitt and the late James Gandolfini partner up as Jackie and Mickey, two hitmen hired to mete out some street justice on the three robbers. Pitt usually does the dirty work personally, acting as a vengeful angel sent to punish those foolish enough to risk their lives by getting involved with the mob.
Although graduates of the Massachusetts Institute of Technology (MIT) have a track record of success in any field, one group of these bright minds opted to put their skills to use by counting cards. The 2008 film puts the corruptive nature of gambling on screen as Ben Campbell (Jim Sturgess) goes from gambling to pay off his $300,000 tuition to becoming addicted to the rush of using his intelligence to become wealthy.
The film is based on the true story of the MIT Blackjack Team, which traveled the world using math to beat casinos at blackjack. Winning is only enough once you want more. Even watching the brightest individuals do the dumbest things in a casino might be enough to discourage anyone from trying it out for themselves.
Molly’s Game by Aaron Sorkin challenges the stereotype that only men can succeed in the high-stakes world of underground gambling. Through her wit and charm, Olympic-level skier Molly Bloom (Jessica Chastain) moves up the ranks from an assistant at one underground poker game to the owner of her own, all while rubbing shoulders with celebrities, wealthy professionals, and Russian mobsters (They seem to be in every gambling film).
Like many great gambling movies, Molly’s Game features high-stakes action in more than just poker. She keeps her money and stays out of jail by betting on the identity of the people who played poker with her. The chemistry between Chastain and Idris Elba’s Charlie Jaffey, Molly’s lawyer, is worth seeing the film for alone. Still, Molly’s Game provides a fresh perspective on the deadly interconnection of seemingly unrelated people and events over a poker table.
Instead of spending nearly three hours seeing a Martin Scorsese classic, you might learn about the sordid history of Sin City by reading about it. Sam “Ace” Rothstein is an unofficial manager of the Tangiers Casino in Las Vegas who answers to the Chicago Mafia. He also serves as the audience’s ears and eyes into the behind-the-scenes workings of Sin City’s gambling industry.
As if they were blueprints, the bribes to the mob, the political battles with the Nevada Gaming Board, the berating of Blackjack dealers, and the showgirls are all examined. To expose the human heart underneath the gaming mirage to unprecedented impact, Casino is one of Scorcese’s epic American tragedies. One of the most concise ways to encapsulate all that gambling means to the world is Rothstein’s comparison of running a casino to “selling people’s dreams for cash.”
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