The Coolest Films about Casinos and Gambling Ever Made

Categories: Blog | Published by: Nicole E. Phillips

10/10/2019

What could possibly equal the sights, sounds, and feelings surrounding you in a casino, or the thrill of the gambler’s rush? Hundreds of movies have been made about gambling, gamblers, casinos, and casino heists. The following list of cool casino and gambling films features some of the most exciting, bizarre, funny, and thrilling casino and gambling scenes of all time.

And some of these films even take place outside of Sin City.

Ocean’s 11 (1960, 2001)

Everyone knows about the 2001 version of Ocean’s 11, where a suave Clooney gathers a team of misfits to rob a bunch of casinos on the Las Vegas Strip. In the ultimate Rage Against the Slot Machine movie, Danny Ocean and his team of crooks manage to pull off the casino heist of the century, and celebrate with a final musical montage in front of the Bellagio’s famous dancing fountain.

The only thing with more metric tons of cool than that is the original Ocean’s 11—with the Rat Pack. In addition to Sammy, Frank, and Dean, the extended Rat Pack includes Joey Bishop, and Peter Lawford. In the original film, the 11 were World War 2 vets who get together to rob several Las Vegas Strip casinos in one night.

While the 2001 version features a scintillating musical score, nothing beats the casino cool of the Rat Pack crooning in dark Vegas lounges. And when Sammy sings ‘Yo-leven’ in a parking lot, you know you’re in for smooth 60s ride in a cool lounge machine…with tail fins.

Bugsy (1991)

Bugsy is a film based on the real-life story of Bugsy Siegel, the New York gangster who helped kick start the Las Vegas Strip. There were casinos in and around Vegas at the time, but they were mostly run-down, honky-tonk joints with wooden saloons and pony rides for the kids. Bugsy brought the glitz and glamour to the desert casino scene.

For a film that’s equal parts history and entertainment, Bugsy chronicles the life of an East Coast gangster who wanted to strike out on his own and build an empire—in the Nevada desert. As Bugsy builds his flagship Flamingo casino, he deals with budget issues, construction misfires, rival gangs, and a serious temper that’s definitely going to be the end of him.

Rain Man (1988)

Who could forget Rain Man, the film which swept the Oscars for the story of an autistic man (Raymond) who counted cards in Vegas? Guided by his scheming brother Charlie (Tom Cruise), the autistic character played by Dustin Hoffman steals the show—and a bunch of chips in Vegas. This film drew a massive amount of attention to the subject of autism. And card counting.

Apparently, one of the positive side effects of Raymond’s type of autism is the uncanny ability to automatically count objects like falling toothpicks and such. Counting cards into the thousands was a logical next step. Angry over the family fortune being left to his autistic brother, Charlie decides to take Raymond’s show on the road—and cheat Vegas casinos with his card-counting secret weapon.

Rounders (1998)

Rounders is one of those sleeper films that didn’t make much of a splash at the box office, yet became a cult classic in the poker community. Matt Damon and Edward Norton play a pair of card sharks who take their show on the road to rook the rubes out of their bankrolls. As they make the rounds, these ‘rounders’ attract all the wrong kinds of attention from all the wrong kinds of people, all the while quoting real-life poker legends like Doyle Brunson and Amarillo Slim.

Rounders is full of exactly the kind of shady characters you would imagine haunting the illicit underworld of backroom poker matches. One such delightfully wicked character is Teddy ‘KGB,’ played by John Malkovich. This guy ticks all the right boxes of evil: he’s intimidating, he’s a card/loan shark, and he’s Russian mafia. His wickedly weird poker tell: pulling apart Oreo cookies and listening to them.

The Hangover (2009)

Some things that happen in Vegas should definitely stay there, especially when you can’t explain how you passed out at a stag party and woke up with someone else’s baby in your room. Rather than ditching the brat and doing a runner on the hotel casino bill (like any rational person does in this situation), the disoriented dudes decide to scour the streets of Vegas seeking answers.

Madcap hi-jinx ensues. Among the mysteries the hungover dudes need to solve: the baby in the wardrobe, the tiger and chicken in the room, and their missing friend, the bachelor. This is what happens when you Viva Las Vegas just a little too much.

Casino Royale (2006)

The coolest casino film has ‘casino’ right in the title; Casino Royale was both a remake of the first James Bond film and a reboot for the 007 series. The film takes place during Bond’s early years, where he has just earned his famous license to kill from the British government. Naturally, the fledgling spy heads to the casino to celebrate.

Fortunately, an international bad guy has arranged a high stakes Texas Hold’em tournament in the Casino Royale in Montenegro. Bond slips into his best tux and Aston Martin, and heads to the casino. Of course, the usual nest of spies haunts the casino, filling the screen with scenes of kidnapping, assassination, poisoning, and Bond trying to save himself with a pen antidote and a car-lighter defibrillator.

Fortunately, a lovely Bond girl slinks over in the nick of time to save the dying spy. But the most suave scene in the movie is when Bond orders his signature Vesper Martini at the casino.

Leaving Las Vegas (1995)

“Did my wife leave me because I started drinking? Or did I start drinking because my wife left me?” This is the burning question on the mind of Nicolas Cage’s loveable drunk character, who wants to leave Las Vegas—by drinking himself to death. In one of the darker tales of Las Vegas, Cage turns in an Oscar-winning performance as a man who just wants to leave the world behind him in a blur of booze.

Naturally, the suicidal screenwriter Ben (Cage) meets the proverbial ‘hooker with a heart of gold’ (Elisabeth Shue), and they bond in booze and debauchery in Sin City. The only agreement in their relationship: she can’t ask him to stop drinking, and he can’t ask her to stop hooking. While gambling is not at the forefront of the plot, Ben does quickly unload some money at the tables, much to his satisfaction. Las Vegas serves as the perfect backdrop for this tragicomic tale of casino noir.

The darkness of the subject matter is punctuated with poignant moments of equally dark comedy: a scene in the shower where Ben reaches for a vodka bottle instead of shampoo, and a dinner scene where he shouts “NURSE!” at his cocktail waitress.

The Cooler (2003)

What happens when you’re on a winning streak so hot you’re about to empty the casino vaults? They send in the Cooler. Just as there are people who seem to be born lucky, there are also people born under a gloomy cloud. Sometimes these sad sacks get jobs as casino coolers.

The Cooler (William H. Macy) is an unlucky guy who works for the casino. His brooding, hang-dog face, combined with a dark and gloomy persona, make Bernie (Macy) the perfect choice to work as the Cooler. When he arrives at a hot table, he almost immediately ‘cools’ the hot streak down to nothing, just by virtue of his gloomy presence. Just add Cupid’s arrow, a girl, and an angry casino mob boss; stir thoroughly.

Fear and Loathing in Las Vegas (1998)

What do you get when you cross the greatest novel ever written about Las Vegas with the crazy animator/director from Monty Python? You get Terry Gilliam’s ‘Fear and Loathing in Las Vegas,’ based on the book by Hunter S. Thompson. This is the epic story of the Gonzo journalist (Johnny Depp) and his psychotic lawyer (Benicio del Toro) on a savage journey through Las Vegas.

We were somewhere around Barstow on the edge of the desert when the drugs began to take hold. I remember saying something like “I feel a bit lightheaded; maybe you should drive. . . .” And suddenly there was a terrible roar all around us and the sky was full of what looked like huge bats, all swooping and screeching and diving around the car, which was going about a hundred miles an hour with the top down to Las Vegas. – Hunter S. Thompson, Fear and Loathing in Las Vegas

The opening line of the book grabs you by the neck and never lets you go. Dr. Gonzo’s words translate beautifully to the silver screen, showing us exactly the kind of things that should stay in Vegas. LSD and psychedelic casino carpeting are 2 things that should never be experienced at the same time.

Casino (1995)

De Niro and Scorsese scorch the screen again; this time in Casino, set in Las Vegas. Robert De Niro plays “Ace” Rothstein, a Jewish American gambling fixer, and Joe Pesci plays “Nicky” Santoro, a mob enforcer. Based on real life mobsters, the 2 team up to conquer the Las Vegas casino scene, one crooked deal at a time.

When watching the film, you really want De Niro to do his typical hothead routine and bash some unfortunate chump. But De Niro is neutered of any violence in his character, and Pesci is scripted with the temper problem instead. Overall, you get a good yarn about the mob era of Vegas, how they schemed, scammed, skimmed, and buried a few bodies in the desert.

21 (2008)

Based on the real-life team of MIT students who counted cards to beat casinos, 21 stars Kevin Spacey as the professor who leads the scrappy team. One MIT mathematics major (Ben Campbell) gets accepted into Harvard Medical School, but alas, he can’t afford the $300,000 tuition. After joining the Spacey professor’s team of blackjack nerds, Ben quickly learns the science of card counting.

In a world where increasing college costs and crushing student debt hamper the brightest minds, one kid stood tall… and took his smart ass to Vegas to whip the tables with his card counting skills. Armed with a team of crack card counters, Ben and his partners go on a gambling frenzy. But drama is lurking in every shadowy casino in the form of jealousy, betrayal, and a very effective, bone-breaking security thug (Laurence Fishburne).

Honeymoon in Vegas (1992)

Most of the films on this list are set in Vegas. Where else? Vegas is a film writer’s dreamscape, full of neon imagery, glitz and glamour, and more Elvis impersonators than you can shake a pelvis at. Long before Nicolas Cage took the boozy way out in Leaving Las Vegas, he played a hapless buffoon trying desperately to have a Honeymoon in Vegas.

This comedy uses ample Vegas clichés about card sharks, kitschy wedding chapels, and Elvis impersonators to form one bizarre stew that flips the rom-com genre on its ear. In short: boy meets girl, boy wants to marry girl in Vegas, card shark steals girl, boy jumps out of a plane with hundreds of Elvis impersonators to win her back. Because that’s how you do it in Vegas, baby.

Lock, Stock, and 2 Smoking Barrels (1998)

Guy Ritchie’s debut crime-comedy masterpiece, Lock, Stock, and 2 Smoking Barrels, is set in the seedy underworld of London. This film features no casinos, but starts off with a plucky young card shark trying to take down a big card room against a notorious cockney gangster, “Hatchet” Harry. When things go terribly wrong for the young card player (of course they do; the game is rigged), he now has to repay a half-million-pound debt to a man named “Hatchet.”

Madcap hi-jinx ensues. Small-time crooks in over their heads embark upon every half-baked scheme imaginable to come up with the money to pay the debt. This ensemble cast of characters introduced Vinnie Jones and Jason Statham to the world, but the film’s slick editing and witty script make it worthy of the cool list. Just watching the frenetic intercuts of fast motion with freeze frame – chips flipping, cards flying, shots drinking, beers toasting, and eyes shifting – makes for one hell of a stylish gambling yarn.

With a list of films about casinos and gambling this cool, it makes you want to binge watch them all, strap a rubber band around a wad of cash, and head to the casino. Tuxedo, Aston Martin, and Elvis jumpsuit optional.

Nicole E. Phillips

Originally from Grand Rapids, Michigan, Nicole studied economics at the University of Chicago before moving to Singapore, where she ended up as a financial analyst at Nomura covering the southeast Asia casino markets. After many years of crunching numbers, Nicole finally decided it was time to switch careers and follow her life long dream of being a writer. Today Nicole regularly blogs on casino related topics while working on her first book, a non-fiction history of the rise of casino gambling in Macau. In her free time Nicole loves to swim, mountain bike and ride horses.

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