Ah, Las Vegas. That's where you'll find Elvis sweating (Elvis), the "Rain Man" winning (Rain Man), and three seriously hungover men retracing their steps (The Hangover).
Yet, while all of these films feature a bit of Sin City, Las Vegas is most known for two things: casinos and gambling.
From heist movies to crime dramas, from comedic to super-serious, there have been all kinds of movies about the ups and downs and wins and losses of the gambling world.
Whether it takes place in a fancy casino or in the smoky backroom of some dodgy underground club, gambling is fundamentally the same everywhere—you take your chances and hopefully walk out alive.
Here are my picks for the best movies about gambling and casinos, with some of the coolest characters to ever grace cinema.
10. Mississippi Grind (2015)
Gambling can be an intense, life-destroying addiction that's as far from funny as it gets. Mississippi Grind, however, features Ryan Reynolds—so, obviously, it's going to have laughs.
His character ends up being incredibly good at gambling, all for one simple reason: he doesn't care if he loses. On the other hand, Gerry (played by Ben Mendelsohn) does. The two meet at a casino in Iowa, and follow one drink with another, and another, and another...
A mugging, a horse race, a game of Texas Hold 'Em, plus a few slot machines later, and the two end up in the deep.
Directors Anna Boden and Ryan Fleck take us all across the South, from Memphis to Mississippi, as they piece together bits, blues, and bumbling characters. Mississippi Grind probably slipped under your radar, but all critics can agree it's a hidden gem.
9. Croupier (1998)
In Croupier, Mike Hodges gives us a neo-noir take on gambling from the other side of the casino—one in which Jack Manfred (played by Clive Owen) is dealer rather than gambler.
That said, Manfred still ends up enveloped by the gambling world, which his girlfriend isn't overly pleased about.
When he's not dishing out Aces, Jack is trying to finish his book—one that's based on a sadistic croupier who loves watching people lose their money. Hm, I wonder who that's based on? Again, his girlfriend isn't happy when she reads it.
Eventually, Jack is roped into the criminal side of gambling, and his story is woven with internal monologues that meditate on how life itself is like a game of dice. And, of course, its success gave Owen's career a boost!
8. Rounders (1998)
A nickname like "Worm" is itself a red flag for a person, and it's made even worse when that person has served time. Played by Edward Norton, Worm is one of those characters whom you hate to love, as his gambling habits tear Mike's world down in a matter of days.
In Rounders, Matt Damon stars as a card-player-turned-law-student who's trying to put his poker days behind him, but that proves almost impossible when Worm tornadoes back into his life.
Like most gamblers, Mike loses more than just his money—but that doesn't stop him from driving towards the lights of Las Vegas for the World Series of Poker.
John Dahl's crime-drama narrates the thrill and addiction of playing from Mike's point of view, even if it just looks like a bunch of guys sitting around a table for hours on end.
7. The Gambler (1974)
Rupert Wyatt's 2014 remake of The Gambler received indifferent reviews because it pales in comparison to the taut 1974 classic. Karel Reisz directed the original movie, in which James Caan's strong central performance was nominated for a Golden Globe.
Axel Freed is an English professor from a family of established doctors and businessmen. However, Axel's not quite as successful as his loved ones believe, running up huge tabs to the ire of his mafioso bookie.
It gets to the point where Axel has to borrow thousands from his mother—and even bet his own life—in order to fund his gambling addiction. While filming, James Caan was battling his own addiction to drugs, and he used that to suffuse his character with a raw sort of desperation.
6. Molly's Game (2017)
Aaron Sorkin's directorial debut tells the true story of Molly Bloom, the Queen of Hollywood's underground poker empire.
Her empire is where all the big names in Hollywood put their riches at risk, including actors, singers, CEOs, tycoons, athletes, mobsters, and more. Unfortunately for Molly, the FBI decide to get involved.
Jessica Chastain delivered one of the strongest, most dynamic female performances of the year as she showed how one woman stood up to the most powerful men in the world without flinching.
The Oscar-nominated memoir runs over two hours without a single dull moment. Tense, entertaining, and carried by incredible performances, Molly's Game has everything a good crime-drama needs.
5. The Color of Money (1986)
The Color of Money brings together Martin Scorsese, Tom Cruise, and Paul Newman. Surely that's enough to send you rushing to watch already? Based on Walter Tevis's 1984 novel, The Color of Money is a kind of sequel to The Hustler (also written by Tevis and starring Newman).
The Color of Money takes place 25 years after Robert Rossen's 1961 drama, with retired pool hustler "Fast Eddie" (played by Paul Newman) teaching Vincent (played by Tom Cruise) how to finesse the game of life. Or, more specifically, the game of pool.
Vincent and Eddie embark on a road trip to all the pool halls, betting and scamming their way to the big bucks. Atlantic City and the nine-ball beckon them, but their combined egos threaten to block the way.
The "color of money" just to happens to match the hue of a pool table, devouring the duo into a blinding world of green.
4. Uncut Gems (2019)
At first glance, Uncut Gems doesn't look like a gambling movie. There are no casinos, roulettes, or stacks of tokens. What it does have, though, is Adam Sandler chaotically pawning Kevin Garnett's NBA Championship Ring to place a six-way parlay on him winning the game.
Despite already owing $100,000 to his loan shark brother-in-law, Sandler's Howard continues to place huge bets while trying to run a jewelry store in the Diamond District. Plus, he's got a looming divorce and employee-girlfriend to fit in.
Everything about the Safdie Brothers' crime-thriller is high-wire and frenzied, just like its haphazard protagonist. And, of course, being a Safdie movie, it was produced by A24, so expect a lot of visceral neon lights that illuminate its dark themes.
Uncut Gems is one of the few gems (no pun intended) in Sandler's memeable filmography. Highly recommended.
3. Hard Eight (1996)
Paul Thomas Anderson's directorial debut established most of the auteur's eventual trademarks: ensemble casts, episodic structures, long takes, isolated characters, etc. His distinct cinematography—often carried out by Robert Elswit—shows his love of exploring human connection.
Hard Eight is a polished, expertly paced crime flick that began life as a 1993 short film called Cigarettes & Coffee. Philip Baker Hall, John C. Reilly, Gwyneth Paltrow, Philip Seymour Hoffman, and Samuel L. Jackson comprise the impressive cast for a debut indie movie.
Like most of Anderson's films, Hard Eight is a slow burn that's devoid of car chases and explosions. That's why we love it!
2. The Sting (1973)
Gambling movies and caper movies often overlap, and that's certainly the case with The Sting. Starring Paul Newman—man, he sure likes to hustle—The Sting follows two pro grifters who try to con the mob.
Directed by George Roy Hill, The Sting unfolds against the backdrop of the Great Depression, swapping out the extravagance of Las Vegas for the dingy backrooms of Illinois.
Shaw (played by Paul Newman) and Kelly (played by Robert Redford) grow increasingly brave with their cons and dive headfirst into dangerous waters—$500,000 kind of dangerous. That's $10 million in 2022!
The Sting was released on Christmas Day. It may not be the most festive film, but it was a hit success and even won seven Academy Awards!
1. Ocean's Eleven (2001)
Here it is—the ultimate heist movie, which happens to take place in a casino! That's pretty smart if you think about it, with casinos holding as much cash as a bank probably does, but also louder, busier and easier to slip through undetected.
Well, it's not exactly easy, but a team of pros who have lots of previous heist experience should be able to pull it off.
The Ocean's Eleven team is made up of conmen, mechanics, surveillance experts, pickpockets, and even an acrobat. They infiltrate the Mirage... and the Bellagio... and the MGM Grand... simultaneously.
Director Steven Soderbergh takes us through all the intricate planning and execution, then wraps up with a satisfying ending. It may not have been showered in Oscar nominations, but Ocean's Eleven is undoubtedly the most famous heist movie of our age.
The stacked ensemble cast includes George Clooney, Matt Damon, Andy García, Brad Pitt, Julia Roberts, and Don Cheadle.