The Best Movies About Gambling

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The Best Movies About Gambling
Even if you’re not an avid gambler, there’s just something about watching a punter put it all on the line for one big score. The risk vs. reward outcome plays even bigger on the big screen; the drama is baked into the plot. Add scheming mafiosos, talented card sharks, and a smoky room full of cash and booze, and you can almost cut the air with a knife.

Each of the following movies about gambling explores a different aspect of the gambling life. Some are entirely about the game itself; others are about the flamboyant characters on the casino scene. Whether the film features a couple of card sharks trying to rook the rubes in Rounders or showcases the grand stage of Las Vegas and the mafia underworld in Casino, the following gambling movies are the best of the best.

The list is in no particular order or rank; we just like these movies for the way they capture the overall spirit of the casino and gamblers themselves.

Ocean’s 11 (2001)

Probably the smoothest, most stylish gambling movie ever made. It’s got swanky swagger set to a jazz-funk soundtrack larger than life. George Clooney is Danny Ocean, a schemer who decides he’s had enough of the house always winning. That and his ex (played by Julia Roberts) is dating a casino mogul. So, the guy must go down—and his casinos with him.

Ocean gathers his motley crew of 11 grifters, conmen, card sharks, and petty thieves to embark on the perfect plan: rob several casinos on the Las Vegas Strip in one night – at the same time. To do this, the plan must be flawless, and each player must play his role to a T.

Based on the 1960 film of the same name, Ocean’s 11 puts Vegas in the limelight again, with a brilliant heist film that ultimately satisfies every gambler’s desire to see the house lose. However, the 2001 version ends on a much more positive note than the first one.

Bonus points if you have seen the 1960 version with the Rat Pack. Frank, Dean, and Sammie bring all the old-school Vegas swagger that put the town on the map. And naturally, each of them croons a tune or two while the ladies swoon.

Casino (1995)

Martin Scorsese’s scintillating epic drama, Casino, is more about the Vegas lifestyle than the actual gambling. It’s about the man behind the curtain, and he is most certainly a mafia man. Based on real-life mobsters, Casino follows the arc of “Ace” Rothstein (Robert De Niro) and Nicky Santoro (Joe Pesci).

Rothstein is the cold, calculating mobster running his slice of Sin City for the syndicate back east. Santoro is his hot-headed thug pal who roughs up the locals from time to time.

The film is set in 70s Sin City before the major mega-resort renovations of the 80s. Very much a film about the end of an era, Casino provides a behind-the-scenes expose on the very real mobsters who reigned in their day.

The definitive Vegas casino film marks the end of the vibrant Rat Pack era, where entertainers and underworld characters were joined at the hip. After stricter gambling license enforcement and new casino investment money hit town, the wrecking ball looms large just around the corner.

21 (2008)

Some casino films really are about the game. 21 tells the real-life tale of a group of MIT students whose blackjack card counting skills beat the house to the tune of millions of dollars. Math professor Micky Rosa (Kevin Spacey) spots raw talent in math student Ben Campbell (Jim Sturgess).

Rosa initially invites his young protégé to his high-stakes poker games, where he teaches him the gentle art of card counting.

Soon the band of merry MIT card counters takes their show on the road and winds up in the hallowed halls of Vegas casinos to play blackjack. With all the money at stake, bitter rivalries ensue, pitting master against protégé.

After much betrayal and backstabbing, 21 deals the cards of fate to see who will emerge as the ultimate victor in the card counting game.

Casino Royale (2006)

You’ve come a long way, Mr. Bond. Ian Fleming’s first 007 novel, Casino Royale, was made into more of a spy parody film in 1967. Decades later, James Bond got a gritty new reboot in the person of Daniel Craig, who plays James Bond in the early days of his espionage career.

The 2006 Casino Royale reboot is one of the best of the Bond films. The new Bond films offer the same flash cars, debonair heroes, and exotic locations as all the others in the franchise. The fight scenes are much more realistic, and the poker game between Bond and villain Le Chiffre (Mads Mikkelsen) almost steals the show.

The film capitalizes on the Texas hold ‘em zeitgeist sweeping the globe at the time. One of the most popular poker variations of all time, Texas hold ‘em keeps gamblers and moviegoers on the edge of their seats with each turn of the cards. Especially when James Bond is betting millions at the table.

Rounders (1998)

More of a cult gambling movie, Rounders sheds a light on the shadows of illegal poker rooms. This modern take on legendary Texas road gamblers like Amarillo Slim and Doyle Brunson is all about high-stakes poker and the men who chase the game all over the map.

‘Rounders’ refers to professional gamblers who travel seeking high-stakes poker rooms, and often, cheaters and cons are part of the action. Matt Damon and Edward Norton play two card sharks hustling their way through backroom poker adventures.

Damon’s character (Mike) is more refined, while Norton plays a two-bit con named ‘Worm.’ The pair need to pay off a large debt to a Russian mobster called Teddy “KGB” (John Malkovich). Mike gets thoroughly trounced by KGB, and now has a massive debt to settle.

Cameos by WSOP pros and the attention to detail in the card games will keep poker enthusiasts hanging on for the entire Rounders ride.

The Cooler (2003)

With all the mob moves and card counting in gambling films, what about Lady Luck? Few films address the casino’s side of things. What happens when a gambler is cleaning out the house on a winning streak that won’t end?

Answer: send in the Cooler. William H. Macy plays Bernie Lootz, a man with luck so bad he can ‘cool’ any winning streak. The owner sends in the Cooler to simply stand at the table in question, and suddenly: the tables turn. The winner begins losing.

If you believe in Lady Luck, meet Mr. Bad Luck. Bernie owes a casino boss (Alec Baldwin) a lot of money, and now he is working it off by employing his natural talent as a professional loser. Bernie’s luck is so bad it affects everyone else at the table.

Enter: romance. Bernie has his eye on a cocktail waitress (Maria Bello), but will the two ever hook up? For the impossible to happen, Bernie’s luck must change in a big way.

The Color of Money (1986)

Gambling isn’t only about cards and dice. In the dusty old halls of gambling, lore lurks the pool hustler. Martin Scorsese brings us another tale of the gambling underworld in The Color of Money, with young buck Tom Cruise as the new kid under the tutelage of master hustler Paul Newman.

Paul Newman reprises his role as “Fast Eddie” Felson from the 1959 film, The Hustler. In that film, the young Paul Newman faces pool hall legend Minnesota Fats (Jackie Gleason).

Now the master has a new student in Vincent (Tom Cruise), whom he tutors in the art of pool hustling. It’s not enough just to be young, arrogant, and gifted, Vincent. You need to know how to lure in the big fish, bait the hook, and take them for every cent they have. This is the Big Hustle.

Vincent refuses to play below his ability and rebels against his master. But Fast Eddie sees the bigger picture. If Vincent can only learn to shelve his ego and play the long game…

Grab the Popcorn!

There you have it: our list of the best gambling movies. This list is far from exhaustive, but you can get a real feel for the casino scene and the thrills and chills of the gambling life in each one.
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