Ah, Las Vegas. It's the city where you'll find Elvis sweating (Elvis), the "Rain Man" winning (Rain Man), and three seriously hungover men retracing their steps (The Hangover). Also, lots of gambling!
Indeed, Las Vegas (nicknamed Sin City) is best known for its casinos and all the gambling that happens therein. From comedic heist movies to dark crime dramas, there are 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 a 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 that capture the thrills and falls that come with the territory.
15. Mississippi Grind (2015)
Directed by Anna Boden and Ryan Fleck
Starring Ben Mendelsohn, Ryan Reynolds, Sienna Miller
Comedy, Drama (1h 48m)
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.
14. The Card Counter (2021)
Directed by Paul Schrader
Starring Oscar Isaac, Tiffany Haddish, Tye Sheridan
Crime, Drama, Thriller (1h 51m)
Gambling films aren't usually bloody, but The Card Counter is. William Tell (played by Oscar Isaac) lives a sad life, moving from one motel to the next, living out of suitcases and covering all the furniture in bedsheets.
In a sense, William is spending his days in sort of afterlife, given that his former life was spent in a military prison. During those eight years, he learned to count cards while serving time for his hand in torturing and abusing Abu Ghraib prisoners (a real tragedy that surfaced in 2004).
There's something about the phrase "enhanced interrogation techniques" that doesn't sit right, and young Cirk (played by Tye Sheridan) is out for revenge on the Major who implemented them. That is, unless William can distract him with the World Series of Poker.
As you might gather, The Card Counter isn't really about gambling at all. It's just used as a lens to explore a very dark piece of recent history.
13. Rounders (1998)
Directed by John Dahl
Starring Matt Damon, Edward Norton, John Turturro
Crime, Drama (2h 1m)
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.
12. Molly's Game (2017)
Directed by Aaron Sorkin
Starring Jessica Chastain, Idris Elba, Kevin Costner
Biography, Crime, Drama (2h 20m)
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.
11. The Gambler (1974)
Directed by Karel Reisz
Starring James Caan, Paul Sorvino, Lauren Hutton
Crime, Drama (1h 51m)
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.
10. Croupier (1998)
Directed by Mike Hodges
Starring Clive Owen, Kate Hardie, Alex Kingston
Crime, Drama (1h 34m)
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 a dealer rather than a gambler.
That said, Manfred still ends up enveloped by the gambling world, which his girlfriend isn't overly pleased about.
When he's not dealing 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!
9. The Color of Money (1986)
Directed by Martin Scorsese
Starring Paul Newman, Tom Cruise, Mary Elizabeth Mastrantonio
Drama, Sport (1h 59m)
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.
8. California Split (1974)
Directed by Robert Altman
Starring George Segal, Elliott Gould, Ann Prentiss
Comedy, Drama (1h 48m)
A lot of gambling films tend to show an exaggerated take on the glamorous, adrenaline-pumping lifestyle of card rooms, pool halls, and Vegas hotels, but California Split adopts a tone of realism to study its two central characters (who inspired the aforementioned Mississippi Grind).
After being robbed by a sore card loser, Bill Denny (played by George Segal) and Charlie Waters (played by Elliott Gould) bond over their mutual, dangerous love of gambling.
Like drug addicts chasing their next hit, the two gamblers are overcome by their hunt for the jackpot—and it doesn't matter where they find it, whether it's from horse racing, boxing matches, or something else.
Robert Altman exposes the grim underbelly of the Vegas scene, where cocaine, violence, and prostitution tangle with roulette tables and betting booths to destroy lives. Somehow, California Split is also a comedy.
7. Uncut Gems (2019)
Directed by Benny Safdie and Josh Safdie
Starring Adam Sandler, LaKeith Stanfield, Julia Fox
Crime, Drama, Thriller (2h 15m)
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!
6. The Cincinnati Kid (1965)
Directed by Norman Jewison and Sam Peckinpah
Starring Steve McQueen, Ann-Margret, Edward G. Robinson
Drama (1h 42m)
Gambling during the Great Depression was either incredibly smart or incredibly dumb, depending on how good your bluff was. After all, your bluff is more important than your hand most of the time.
Lancey Howard (played by Edward G. Robinson) somehow always has a good hand when he's at the card table, which marks himself out as a legend in old 1930s New Orleans.
Eric Stoner (played by Steve McQueen), also known as The Cincinnati Kid, is the young, cocky, and eager-to-card-duel newbie on the block who's dying to try his luck against the master.
Thirty hours at the card table is nothing to professional players like Lancey, who trades an achy back for thousands of dollars in cash. But has he finally met his match with The Kid? Or will The Kid loose his cool guy status to a straight flush?
5. Hard Eight (1996)
Directed by Paul Thomas Anderson
Starring Philip Baker Hall, John C. Reilly, Gwyneth Paltrow
Crime, Drama (1h 41m)
Paul Thomas Anderson's directorial debut established most of the auteur's eventual trademarks: ensemble casts, episodic structures, long takes, isolated characters, etc.
Furthermore, 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 this 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!
4. The Sting (1973)
Directed by George Roy Hill
Starring Paul Newman, Robert Redford, Robert Shaw
Comedy, Crime, Drama (2h 9m)
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 $11 million in 2023!
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!
3. Ocean's Eleven (2001)
Directed by Steven Soderbergh
Starring George Clooney, Brad Pitt, Julia Roberts
Comedy, Crime, Thriller (1h 56m)
Ocean's Eleven is the ultimate heist movie, and it just so 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 con men, mechanics, surveillance experts, pickpockets, and even an acrobat. They infiltrate the Mirage... and the Bellagio... and the MGM Grand... all at the same time.
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.
2. The Hustler (1961)
Directed by Robert Rossen
Starring Paul Newman, Jackie Gleason, Piper Laurie
Drama, Sport (2h 14m)
The aforementioned The Color of Money is a crowd-pleasing pick for most audiences, but if you're after something classier and more cultured, try its black-and-white predecessor The Hustler.
In this one, Paul Newman is cool as a cucumber as the younger version of Fast Eddie, still making a name for himself in the gangster-like world of gambling (for all its reputation and nicknames).
To prove himself, Eddie challenges top dog Minnesota Fats (played by Jackie Gleason) to a high-stakes game of pool. The Hustler isn't just one of the best gambling movies, but best sports movies of all time.
1. Casino (1995)
Directed by Martin Scorsese
Starring Robert De Niro, Sharon Stone, Joe Pesci
Crime, Drama (2h 58m)
If it's a Martin Scorsese and Robert De Niro collab, then it's probably going to take top spot—no matter what the subject is about! And when it comes to the greatest casino movies, what could make a better first-place pick than a film titled Casino?
Of course, being a Scorsese and De Niro movie, you know there's going to be some serious gangster undertones. As it turns out, gambling and gangsters go hand-in-hand, and for this Scorsese film, it's the Chicago Outfit that serves as the focal crime unit.
Set in a dazzling 1970s Las Vegas, Robert De Niro's Sam "Ace" Rothstein is an expert gambling handicapper who's asked by the Chicago Outfit to run Tangiers Casino on their behalf.
It's not quite Goodfellas (although Joe Pesci does play a similar, psychotically inclined character in both films), but Casino is just as bold, stylish, and slick as any other Scorsese picture of its kind.
