California Split. Photo: Courtesy of Columbia Pictures

Movies about gambling have an inherent drama because, by definition, they’re about risk. It’s not fun to watch someone be prudent and cautious, but to see someone constantly putting his well-being on the line in desperate, irrational hope for that One Big Score … well, gamblers in gambling movies are in many ways just like that veteran cop who takes One Last Case before retirement. They usually don’t end up with a calm home life upstate, counting their winnings.

So, with the annual gambling bonanza that is the Super Bowl coming up, we decided to take a look back at some of the best movies about gambling. A note on methodology: We tried to make sure we emphasized the gambling over the movie. Few would argue that Rounders is better than Casino, but Casino is less about the gambling and more about the world in which that gambling takes place; Rounders is definitely about the gambling. We veered more toward movies about the gambling. Luckily, a whole lot of them happen to be great movies all on their own.

All right, so we know this isn’t a very good movie: It’s probably the worst Vacation movie, with the possible exception of that terrible reboot with Ed Helms. But you’ll have to just indulge us on this one, because it has perhaps the single funniest, dumbest casino joke of all time. Basically, Clark Griswold develops an addiction to gambling and is tormented by a card-dealer named Marty played — awesomely — by Wallace Shawn. Clark is so bad at gambling that, at one point at a “discount” casino, he forks over $20 to play a game called “Pick a Number Between 1 and 10?” He guesses “4.” The dealer says “nope, 7,” and … just takes his money. Clark storms away, grumbling to himself. The idea that such a game would exist basically sums up Las Vegas, and gambling in general. It’s maybe the most honest possible card game.

Made in the heat of the now-mercifully-cooled World Series of Poker craze, the late Curtis Hanson put an immediate halt to his terrific L.A. Confidential/Wonder Boys/8 Mile/In Her Shoes run with this mostly hackneyed story of a superstar poker player (Eric Bana) with a complicated relationship with his even bigger superstar poker-player father (Robert Duvall). We have seen that story a million times in a million better sports movies — this even has a Big Game at the end — but both Bana and Duvall find some truth in their characters regardless. This movie was a disaster at the box office, and Hanson’s hot streak was over.

Based on the true (if embellished by author Ben Mezrich) story of the MIT Blackjack Team that beat the house for nearly a decade, 21 turns an interesting math and business story into a sort of dumb heist movie featuring a lot of young, handsome actors (Jim Sturgess, Kate Bosworth, Aaron Yoo, Jacob Pitts, and even Josh Gad) trying to pull one over on Kevin Spacey. Spacey is particularly checked-out here, and the movie was criticized for “whitewashing” in its casting, turning the mostly Asian-American real-life players into generic white people. But for a brief moment, before Spacey is being kidnapped and beaten in a hotel room, it’s an interesting look at the science behind smart gambling. But only for a moment.

An odd little comedy about a perpetual loser gambling addict (Richard Dreyfuss) who, for one day, hits on every single bet at the horse races. This just inspires him to push harder and keep it going, and while this might turn out to be a disaster in a movie like, say, Uncut Gems, here, it’s just a wacky ’80s comedy. Let It Ride still gets a lot of comedic mileage out of Dreyfuss’s mania and goes a long way on some very fun supporting performances from Teri Garr, Jennifer Tilly, and David Johansen. But let’s just say they don’t show this one at Gamblers Anonymous meetings.

There was a time that Mel Gibson was considered such a light and lively leading man that a big-budget studio movie could coast on his charm as a card shark and con man. Based on the popular ’50s television series (and co-starring that show’s lead, James Garner), Maverick is a bit of a bloated contraption, too long and too overstuffed with would-be-epic-and-probably-unnecessary Western scope by Richard Donner. But the film still has its pleasures, not least of which is Gibson’s pal Jodie Foster, who has a blast playing the sort of damsel-in-distress female sidekick role she’d otherwise spent most of her career avoiding. It’s a gas to watch her so giddy.

This likable indie’s best quality is its premise: Meet Bernie (William H. Macy), a professional loser whose job it is to ruin any high-roller’s hot streak simply by playing at the same craps table. The Cooler starts off as a sad, funny character study of a recovering gambling addict who’s still in massive debt to Alec Baldwin’s tough-guy casino boss — he’s working off what he owes by being the guy’s go-to “cooler” — but the love of a good woman (Maria Bello’s weary cocktail waitress) might just change his luck. Realism takes a backseat to romance and crowd-pleasing sentiment in Wayne Kramer’s directorial debut, and the followthrough isn’t as entertaining as the setup. But Macy was born to play this sort of hangdog failure who hasn’t stopped betting on himself.

Often, movie characters who gamble are presented as sobering cautionary tales. Nobody told Steven Soderbergh, who turned his remake of the creaky Rat Pack caper into a jazzy, fleet-footed blast. From the early scene where George Clooney and Brad Pitt’s ultra-cool characters square off at the card table, it’s clear that this Ocean’s Eleven will exude the sleek, cocky spirit of modern Vegas, which is all upscale adult pleasures and very little actual degenerate behavior. Soderbergh’s ensemble is impeccably dressed and never fussed, sporting the swagger that real gamblers wish they had. The filmmaker isn’t interested in the intricacies of gambling, and he also thinks the games’ metaphors are equally silly — as demonstrated by one of the film’s best moments:

If you chafe at Aaron Sorkin’s showy, know-it-all attitude in his screenplays, then be warned: His directorial debut is the Oscar-winner at his Sorkin-iest. Molly’s Game is based on the memoir of Molly Bloom, a former champion skier who shifts careers after a terrible accident, turning her attention to the world of underground poker. Jessica Chastain is coiled-cobra cocky as Molly, walking us through this illegal but highly addictive and lucrative ecosystem as she becomes the queen of organizing high-stakes games. This thriller is far too proud of its own cleverness — a chronic Sorkin shortcoming — but you feel Molly’s rush, and you meet some truly heartbreaking characters, including Bill Camp’s hopeless gambler. It’s horrifying to watch him drown in slow motion.

“In Vegas, everybody’s gotta watch everybody else.” In 1973, Robert De Niro played the dangerous, unpredictable hothead opposite Harvey Keitel’s sensible mobster in Mean Streets — a couple decades later, it was De Niro as the man with the weight of obligations bearing down on him. In Casino, he’s Ace, a gangster running a mobbed-up casino who’s trying to do things “the right way,” only to be undercut by his hotheaded pal (Joe Pesci) and an ambitious woman (Sharon Stone) he shouldn’t trust. Want to understand the inner workings of Vegas gambling? Martin Scorsese’s intricate drama is for you, chronicling Sin City’s evolution from seedy to sanitized over the span of several years. As he did previously with GoodFellas, Scorsese understands how American enterprise works in the criminal underworld — and also how individuals get trampled on along the way.

When you consider the parameters of our gambling movie rankings, we must say, The Hustler isn’t as good a gambling movie as its sequel, The Color of Money, (which you will find later on this list) … but it probably is a better movie overall. The 1961 original is less concerned with a swaggering Tom Cruise–Paul Newman movie-star face-off and more focused on loyalty and integrity and ambition. Newman’s Fast Eddie Felson is like a more interesting version of Cruise’s character, and his battle to take down Jackie Gleason’s Minnesota Fats follows a more human, soulful narrative than a typical sports-movie arc. It’s better the less it is about the pool hustling … which is great, but keeps it lower on this list.

An origin story of Las Vegas, Bugsy is principally a study of Bugsy Siegel, a gangster who travels to the desert, convinced he’s seen the mob’s future. Lavish, classy, and smart, director Barry Levinson’s Oscar-winning drama follows Siegel in his seemingly quixotic dream of creating a mecca of gambling and casinos, and Warren Beatty keenly plays him as a man of passions but perhaps not enough reason. Bugsy is less about gambling — although Siegel surely takes some big chances — than it is about Sin City’s messy birth, which proves fascinating, even if the movie’s glitzy, prestige-picture trappings are a bit limiting.

Today, the legalization of gambling has become a Hail Mary last-ditch effort for many financially eroding urban areas like Detroit, St. Louis, and others — but Atlantic City did this first. Louis Malle’s heartbreaking but still charming, even regal Atlantic City captures both the blight of Atlantic City — which led to the legalization of gambling there in the first place — and the hope among the poor dreamers still hanging around its edges. With a screenplay written by John Guare, the film features an honest, old-school movie-star performance from Burt Lancaster and a riveting turn from a young Susan Sarandon as a casino waitress with dreams of being a dealer but an ex-husband she can’t shake. The movie feels both dated and timeless, capturing a specific moment that has the power of folklore.

John Sayles’s historical drama about the Black Sox scandal of 1919, when members of the Chicago White Sox (including legend Shoeless Joe Jackson) threw the World Series to gamblers, is particularly instructive today, when professional sports have embraced gambling revenues wholeheartedly, ignoring the lessons of the past. The story of Eight Men Out is less about corruption from the players than it is a labor-management conflict: The players fix the series not out of greed but out of desperation when their owner refuses to reward them for an incredible season. Gambling’s corrosive influence on sports has mostly been forgotten in the recent years, but Eight Men Out reminds us of its perils.

Paul Newman won his only Oscar for The Color of Money, revisiting the character of Fast Eddie Felson, whom he played in 1961’s The Hustler. The sequel is a movie about an aging pool shark at a crossroads. “He had to stop gambling,” Scorsese said in Conversations With Scorsese. “He had become a different kind of hustler in a way, selling liquor. But he couldn’t resist the joy of the game. I mean, not just pool, but livening up the game of life, which is the real gamble.” That quote undersells the film’s cautionary tone — how it portrays its characters, including Tom Cruise’s upstart pool player Vincent, as individuals who have thrown away their lives on a game that doesn’t love them back. This isn’t one of Scorsese’s best movies — and as we said earlier, The Hustler is the better overall film — but it’s solid and despairing. Like with Scorsese’s mobsters, these are people who are magnetic but not ones you’d want to spend time with in real life.

Who says gambling can’t be really fun? This Best Picture winner exudes pure pleasure … well, unless you run afoul of Shaw (Paul Newman) and Kelly (Robert Redford), that is. These two con men decide to take down a no-good mobster (Robert Shaw), and their elaborate grift involves card games and horse racing. Understanding the machinations of Shaw and Kelly’s plan doesn’t matter — it’s just a delight to watch the characters (and director George Roy Hill) turn The Sting into one big, electric narrative sport. These are some winners who are easy to root for.

When you strip away all the supposed glamour and glitz of gambling and focus on the crippling, oppressive addiction, you get Owning Mahowny, the true story of a Canadian bank manager (Philip Seymour Hoffman) who stole money from his bank and used it to make a series of increasingly dangerous bets in Atlantic City. Hoffman, as you might expect, is brilliant in the role, elusive and pathetic in equal measure, a man who is helpless to control himself but does his best to hang on as long as he can regardless. The movie is so tuned in to Hoffman’s frequency that it’s almost too distant to the viewer: His Mahowny is so locked in his own head that there’s no way for us to get in. But this is probably as close to the terror of what it’s actually like to have a gambling addiction as a movie can probably get.

We say this every time we write about Rounders, but it remains true: “It’s basically Citizen Kane for gambling addicts and … perfectly fine for everybody else.” That puts it higher on this list than it would be on almost any other, but it does do an excellent job of capturing the swaggering, dopey masculinity of being a professional poker player. (Or at least of being one in the late ’90s.) We’re glad Matt Damon eventually grew out of these roles, but a supporting cast like this (John Malkovich! John Turturro! Martin Landau! Famke Janssen! Even Bill Camp!) can’t help but populate this with people who make a mostly artificial world feel real and lived-in. Still: See The Cincinnati Kid, people. (That’ll be coming up on this list shortly.)

Before they jumped aboard the Marvel bandwagon, Half Nelson filmmakers Anna Boden and Ryan Fleck crafted this lovingly retro two-hander about a couple of inveterate gamblers driving down south to a New Orleans poker game with potentially big payoffs. This might be Ryan Reynolds’s best performance: He’s terrific as the backslapping Curtis who befriends the troubled Gerry (Ben Mendelsohn). Addiction, depression, and regret are the hallmarks of Mississippi Grind, which doesn’t try to hide its debts to 1970s Hollywood — specifically, a certain Robert Altman film that will appear later in these rankings. But that cinematic referencing does nothing to blunt the material’s desperate, melancholy pull. Mississippi Grind practically reeks of stale cigarettes and half-drunk cans of beer: It’s a portrait of nonstop gambling as one sad grind.

Clive Owen has been such a familiar, somewhat disappointing, presence in films for the last two decades that it’s now hard to remember what a lightning bolt his arrival was. So go back and rewatch Croupier, where all that promise was laid out fairly magnificently. He’s Jack, an aspiring novelist desperate for money — soon, he’s a croupier getting to know the world of casino gambling. Pitched like a hard-boiler noir — Jack has the blasé seen-it-all vibe of a private dick — Croupier explores the sweaty anxiety and crippling sadness of those who have thrown their lives (and money) away at the tables. If the plot complications aren’t always satisfying, the film’s vivid recreation of dingy casino life is utterly intoxicating. It’s a shame that Owen has rarely found a film since that’s so magnetic.

Considered a bit of a knockoff of The Hustler at the time, this movie, which concentrates on poker rather than pool hustling, holds up just as well as that film, and maybe even better, if just because people do a lot more poker-playing than pool-hustling anymore. It also has a classic Steve McQueen performance as “the Kid,” a cocky player who learns he’s maybe not as great as he thinks he is. The movie feels current and taut and relevant. Put it this way: All the bros you know who think Rounders is the best movie ever clearly haven’t seen this.

5. Tricheurs (1984)

The best gambling movie you’ve never heard of. Right before Barbet Schroeder gave us Barfly, Reversal of Fortune, and Single White Female, he made this mad, irresistible little thriller about a charming man (played by French rock star Jacques Dutronc) with such a desperate addiction to gambling that he ultimately doesn’t really care if he wins or loses. That becomes an even bigger problem when he meets up with a man who enlists him in a complicated cheating scheme that just raises the stakes to an unmanageable level. Tricheurs isn’t judgmental of these gamblers and cheaters: It just follows them along to their inevitable doom. Not that the trip isn’t a wicked, dark blast regardless.

Paul Thomas Anderson’s first film, an expansion of a short film he made called Coffee & Cigarettes (and starring a character called Sydney that Philip Baker Hall previously played in Midnight Run), was a major pain for the neophyte filmmaker, a movie he nearly lost the rights to (and whose title he famously hates). And while it can’t stand up to PTA’s masterworks, it’s a remarkable debut, a study of a sad, lonely man who has learned to survive in the underworld of Las Vegas by being quiet and unassuming until he meets people who might actually need his help. It’s less showy than you’d expect from Anderson’s first film — he was saving his truly bravura stuff for Boogie Nights — but it’s deeply moving: The movie seems to understand Las Vegas, and the men you never notice when you’re there, on an almost transcendent level. And Philip Seymour Hoffman’s one scene is immortal:

Every time we see the “This is how I win” meme on social media, we can’t help but think … you know, that moment in Uncut Gems is really heartbreaking. For all the well-deserved discussion about the fact that Josh and Benny Safdie’s thriller is incredibly intense, what gets left out is precisely why it’s so nerve-wracking. And that’s because Howard, wonderfully played by Adam Sandler, is a hopeless gambling addict who cannot stop until he destroys himself utterly. The brilliance of Uncut Gems is in Howard’s ability to get us sucked into his sickness, making us think, even for a moment, that, yes, he might be able to pull off this crazed caper he’s concocted — yes, maybe this is how he wins. Never once moralizing about their doomed protagonist, the Safdies inject his mania directly into our veins, riding along on his crazed rush. Yet here’s the craziest part: After seeing the film’s tragic finale, you may want to get right back on the ride immediately. Addiction is sort of like that.

James Toback, who has since been hit with allegations of all kinds of problematic behavior, based his screenplay on his own gambling addiction, but what’s great about The Gambler — the 1974 James Caan version, obviously, not the 2014 Mark Wahlberg one — is that the title character is less obsessed with gambling than he is with danger, even self-destruction. His Axel makes bets simply to dig himself deeper and deeper into trouble, even arguing that, for him, the fun of betting is losing. That’s a perilous situation for a gambler, to say the least, but Caan sells us on Axel’s desperate chase for the next rush. Axel isn’t betting on basketball: He’s playing Russian roulette.

The story goes that Robert Altman sent Elliot Gould the screenplay to California Split, hoping he’d play Charlie, a gambler who befriends fellow gambler Bill (George Segal). “I’ve always wanted to play this guy,” Gould told the director, to which Altman replied, “You are this guy.” Hopefully not — Charlie’s addiction is pretty severe — but the actor exuded his laid-back charm to wonderful effect while working with Segal, who wasn’t that interested in gambling. And yet the two men’s rakish charm, in one of the high watermarks of ’70s hangout cinema, makes this not just a great buddy movie but a beautiful exploration of boys-will-be-boys friendship. And, of course, there’s a whole lot of gambling, which Altman films with casual mastery, letting us eavesdrop on the weird characters and dangerous oddballs who populate that world. California Split remains perhaps the director’s most underrated classic — and its gut-punch ending is so muted, yet so perfect.

Grierson & Leitch write about the movies regularly and host a podcast on film. Follow them on Twitter or visit their site.