Photo: Matthias Tunger (Getty Images)
So you’re in the mood to gamble. Maybe you’re suddenly flush and the money’s burning a hole in your pocket. Or maybe you’re hoping to hit the jackpot so you can finally pay off your student loan debt. Either way, proceed with caution.
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Before you try your luck at the casino, wise up with these Mandatory Movies on the risks and rewards of being a high roller. While it might be fun to double down, go all-in, or bet the farm, you may want to consider a safer haven, like a 401(k), for your funds.
Oh, who are we kidding? Go on, get in the game. Just keep your dealings aboveboard.
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Mandatory Movies Gambling
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'Molly's Game'
If you think you’re the smartest guy in the room, think again. The "smartest guy" just might be a woman. Such was the case in the real-life story of Molly Bloom (Jessica Chastain), a former Olympics-level skier who ran one of the most exclusive poker games ever. Celebrities, royalty, and mobsters alike all played at her table…until the law caught up with her.
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'Casino Royale'
Secret Agent James Bond (Daniel Craig) is on a mission – his first as 007 – to Casino Royale in Montenegro in hot pursuit of a banker to terrorists who also happens to like poker. Can Bond hold his own at the big boys’ table and get the bad guys? Of course he can (doesn’t he always?) but watching him do so is oh-so-fun.
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'Rounders'
Is poker a young man’s game? Law student Mike McDermott (Matt Damon) has his doubts after losing everything to a Russian player, Teddy KGB (John Malkovich). But then Mike’s old gambling pal, Worm (Edward Norton), reappears on the scene. Worm is under pressure to make good on a prison debt and he needs Mike's help. In no time flat, Mike gets dangerously enmeshed in Worm’s shady dealings. Are these two heads better than one ruski? Place your bets before the movie begins.
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'Casino'
This unrelenting and violent Martin Scorsese flick follows Sam 'Ace' Rothstein (Robert de Niro) who’s hired by the mob to run the Tangiers casino in Las Vegas. All’s well until Ace’s childhood buddy, Nicky Santoro (Joe Pesci), comes into town and starts trying to claw (and kick and punch and torture) his way to the top. Complicating matters is Ace’s wife, Ginger (Sharon Stone), an alcoholic, drug-abusing MILF who can’t be trusted.
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'Leaving Las Vegas'
In one of Nicolas Cage’s best performances ever, he plays Ben Sanderson, a screenwriter who burns all his bridges at home and work before setting off for Las Vegas, where he plans to drink himself to death. While gambling doesn’t take center stage in this gut-wrenching and unforgettable film, Ben does get thrown out of a casino after losing it in a booze-fueled rage. But what Ben is really gambling with is 1) his life and 2) his heart, especially after he falls for the stunning, take-no-shit hooker Sera (Elisabeth Shue). All bets are off when alcohol’s involved.
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'The Gambler'
Following his grandfather’s death, arrogant and entitled English professor Jim Bennett (Mark Wahlberg) gambles away his grief at a secret casino. Now he’s in massive debt to a gangster and the casino owner and the payback clock is ticking. After his mom reluctantly forks over $260,000, Jim is dumb enough to lose it gambling while trying to impress his student crush. Can he figure out plan B before he’s forced to pay what he owes with his life?
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'Oceans Eleven'
Oh, come on, you’ve seen this film 1,000 times already. We'll spare you the synopsis. Go watch it again.
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'Hard Eight'
Sydney (Philip Baker Hall) knows his stuff when it comes to gambling. John (John C. Reilly) is a penniless loser who doesn’t have a clue. John learns the tricks of the trade from Sydney and even marries a casino cocktail waitress named Clementine (Gwyneth Paltrow), but nothing good ever lasts, not in money or in love.
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'The Cooler'
Bernie Lootz (William H. Macy) is a cooler. Yes, that’s a job title. It’s the casino employee who brings bad luck to winners. At the Shangri-La Hotel and Casino in Las Vegas, Bernie does his job, day in and day out, limping about and ruining winning streaks. Then he meets waitress Natalie Belisario (Maria Bello) and his luck begins to change.
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'Vegas Vacation'
Gambling movies are so dark and depressing. We had to throw at least one laugh-fest in here to lighten the mood. You know what you're getting when you watch a Vacation flick, and while this one isn't quite as funny as its predecessors, it'll do as a palate cleanser for all the other stomach-churning gambling movies you just binge-watched.
