Big-Screen Gems: A Dozen Gambling Films To See From The Past 50 Years

As Adam Sandler generates Oscar buzz in Uncut Gems, we take a fresh look at some of the best gambling movies of the last 50 years.

The critical praise in recent weeks for the gambling film Uncut Gems and for its lead performance, by Adam Sandler as an out-of-control sports bettor, prompted us to ponder some of the most notable gambling films of the last half-century.

Below is a list of a dozen movies worth your time, whether in a theater or at home by streaming video. There are no Academy Award winners among them, but they’re recommended for any number of reasons.

Some take a look, with varying degrees of accuracy, at real-life crimes or scandals that many gamblers may already be familiar with, or should be. Some are directed by among the top filmmakers of their generation. Some depict the highs and lows of casino gambling and sports betting in a way that you may already fully understand but can educate your spouse or friends about with a viewing.

And there are some tough depictions here of addictive behavior, beatings arranged by bookies, lies told to family members, emotional abuse of girlfriends, bad beats taken on sporting events and river cards, and many other unpleasantries that you hopefully haven’t had too much personal experience with.

But just like in real life, sometimes these movie characters get lucky, too, and the chips stack in a way you’d love to imagine for yourself, leading to a happy ending (though we won’t tell you which films finish like that).

So feel free to pull up a chair, read what’s below, get your thumb ready on the remote, and visit any number of casinos, racetracks, and card rooms across America — both real and imagined — to get Hollywood’s sense over these past 50 years of what gambling is all about.

Uncut Gems (2019)

Adam Sandler will make you forget that he’s a comedian within the first few minutes of Uncut Gems, his latest film, in which he plays a desperate and unlikable Jewish jewelry dealer in New York City. Sandler’s Harry Ratner is heavily in debt and is continually looking for his next big score.

An addicted gambler, Ratner puts money that isn’t really his on two games of the 2012 Boston Celtics-Philadelphia 76ers NBA Eastern Conference semifinal series. From a sports betting perspective, there’s plenty wrong with the storyline — both bets are parlays that start out with the opening tip, and the ease with which Ratner places the bets isn’t quite believable. Though sports betting wasn’t legal outside of Nevada in 2012, Ratner has his biggest bet placed at Connecticut’s Mohegan Sun, which not only didn’t have legal sports betting in 2012, it still doesn’t now. In addition, parlays are often attractive to bettors because of the high odds, and they certainly help build drama in the film, but experienced bettors often shy away from them. Plus, with the high house risk involved if they hit, your standard bookie and casino would be wary of taking a massive wager on them.

Remarkably, Ratner makes all the right picks, but as you’ll see if you watch the film, the payout is elusive. A pleasant surprise is former NBA star Kevin Garnett playing himself, and doing it gracefully and professionally. Just as it’s easy to forget that Sandler is a comedian, it’s easy to forget that Garnett is a superstar on the basketball court.

On balance, this frantic, raucous, dark, and sometimes confusing film is Sandler’s best dramatic work.

See full review here.

(In theaters now. Review by Jill Dorson)

Inside Game (2019)

Inside Game, which chronicles the circumstances of the scandal involving NBA referee Tim Donaghy, offers a tough look at the downward spiral of a man who became obsessed with gambling.

Donaghy had officiated in the NBA for 13 years before being caught providing inside information to longtime friends who were involved in gambling and making frequent bets on games himself while officiating. He pleaded guilty in 2007 and served time in prison.

The film of his story has the standard hookers-and-blow theme, but the acting is good enough to make it captivating anyway. The opportunity for Donaghy, as a referee, to have insight into player health conditions just minutes before tipoff is accurate — and alarming, because those opportunities remain.

The movie doesn’t play out as some sort of morality play against gambling, which would be dull. It just explores what can happen to a person who can’t stick to the occasional casual wager, but who instead becomes consumed by winning, by any means necessary.

In the end, decisions have to be made between lifelong loyalty and self-preservation, a theme that transcends mere gambling.

See full review here.

(In theaters in limited release. Review by John Brennan)

Molly’s Game (2017)

What’s this, a gambling film with a female lead? You won’t find that elsewhere on this film list.

But you’ve undoubtedly heard of this movie, as it was so recent and well-publicized, with an A-list cast backing writer/director Aaron Sorkin, and also because the true-life story of Molly Bloom has received such attention.

The film is based on Bloom’s book about how she spent a decade running high-stakes house poker games for movie stars, athletes, and business titans in Los Angeles and New York before the games got entangled with mob figures and she was busted in 2013 for taking an illegal rake.

It’s a fast-paced, slick film by comparison to many on this list, and Jessica Chastain’s portrayal of Bloom, a young and attractive poker ingenue when her role in the games began, earned her a Golden Globe nomination. Sorkin received Globe and Academy Awards nominations for his writing.

Part of the fun in watching is trying to match up the poker players with the real-life celebs who have been publicized as taking part in Bloom’s games, such as Leonardo DiCaprio, Ben Affleck, and Alex Rodriguez. One obnoxious character in the film is referred to only as “Player X,” widely believed to be a stand-in for actor Tobey Maguire, whom Bloom described in her book as a first-class douche.

(Available by YouTube rental. Review by Gary Rotstein.)

Win It All (2017)

Comedian Jake Johnson shared screenwriting credit while starring as addicted gambler Eddie Garrett in this little-publicized but well-received (85% approval on Rotten Tomatoes) Netflix dramedy.

Eddie’s an aimless Chicago parking lot attendant who spends long hours in an underground casino in the city, interrupted by banter over beers with buddies and amusing lectures from a well-intentioned brother with a more conventional lifestyle.

Everything in Eddie’s life changes — for both better and worse — after an acquaintance headed to prison drops off with him a duffel bag full of cash for safekeeping. Eddie can’t help but “borrow” the cash to support his casino play, track visits, and card playing. Big problems ensue, naturally, with the plot revolving around how he navigates them and attempts to normalize his life with a new job and girlfriend.

Veterans of Gamblers Anonymous will recognize the meetings Eddie walks into and the words he mouths, but they may be dismayed by advice he receives when desperate from his sponsor, Gene (fellow comedian Keegan-Michael Key): “I’m going to say the worst thing a sponsor can say — I know a high-stakes game I can get you into.”

We’re guessing that would get Gene crossed off the sponsorship candidate list for most meeting groups, but Win It All otherwise quietly, effectively, sometimes humorously depicts the strong draw of gambling upon so many.

(Available on Netflix. Review by Gary Rotstein.)

Mississippi Grind (2015)

We will bet that Mississippi Grind is the best gambling movie you’ve never seen. And then we will double down on its being the best one about gambling in which no character sets foot in Las Vegas or Atlantic City.

The realistic, indy film with outstanding lead performances by Ryan Reynolds and Ben Mendelsohn had a small, arthouse film rollout a few years ago and holds up quite well via a streaming service today.

Like the characters in the better-known California Split (see below), the smooth, confident Curtis (Reynolds) and slouching, hangdog Gerry (Mendelsohn) meet in a poker room, bond afterward at a bar, and set off on gambling adventures thereafter. Gerry calls Curtis the “handsome leprechaun” who unexpectedly appeared in his life to change his fortunes. Well, maybe.

They form an unlikely pair that gain honest affection from the audience as well as one another as they set off from Iowa in a Subaru station wagon that takes them to casinos and house games and acquaintances in St. Louis, Memphis, Little Rock, Tunica, and finally New Orleans, where there is to be a $25,000 buy-in house card game.

But like Curtis often says, “The journey’s the destination.” That journey includes an excruciating two-outer bad beat on the river that every Texas hold’em player has experienced, as one of many turns and misdirections that show up in the plot. The “Mississippi Grind” of the title is a horse they bet big on, though it also references their entire lifestyle.

But you won’t remember the storyline as much as the well-drawn, studied characters and Americana settings that few big-budget films would ever spend time on. Maybe that’s why this one made such little money from so few people seeing it — what a shame.

(Available on Netflix. Review by Gary Rotstein.)

21 (2008)

The film 21, about a team of MIT math prodigies making small fortunes from card-counting at blackjack in Las Vegas, opened as a box office smash.

That success speaks more, perhaps, to the nation’s fascination with gambling than with the quality of the film, which received mixed reviews. Or perhaps Americans just flocked to it hoping to gain any edge they could to beat casinos themselves.

The movie does do a good job of depicting that tough strategy of card-counting and how it can be deployed in real life, as described in the book Bringing Down the House, upon which the film was based. Just don’t believe everything in the movie, like, oh, the ethnicity of the team, its leadership by a professor, the romance between team members, wild partying they enjoy, beatings they take from casino security, big thefts and chases, and untold other things. That’s Hollywood stuff.

Relatively unknown Jim Sturgess has the main role in the film, playing an MIT whiz based on real-life Jeff Ma (a consultant to the film), who was recruited to join other students making weekend trips to Vegas to beat the house at blackjack by upping bets when the cards still remaining in the shoe favored them.

21 is impossible to watch, however, without having some focus redirected on Kevin Spacey’s performance as the manipulative, seductive, bullying (and mythical) professor in charge, considering all of the allegations against him in real life since the film was made.

A blackjack player will appreciate watching the strategy involved. An amateur gambler will enjoy watching the house taken down. A stickler for detail, especially one with a modern distaste for Spacey, might want to steer clear.

(Available on Netflix. Review by Gary Rotstein.)

Owning Mahowny (2003)

On Dec. 1, 1985, the Atlantic City Caesars was compelled to shut down gambling for a day as part of punishment from state regulators for its wooing of a Toronto bank assistant manager addicted to gambling.

The story of that gambler (Brian Molony in real life, Dan Mahowny in the movie) and how he embezzled some $10 mm from one of Canada’s largest banks to feed his habit are told in a low-key film that features a masterful performance from Philip Seymour Hoffman. Roger Ebert put the understated and underrated movie on his 2003 Top Ten list.

To be fair up front, there’s little fun to be found in Owning Mahowny. But with chilling honesty, it shows as well as possible — through Hoffman’s sober performance as a smart, unemotional, but compulsive schlub — the hot streaks, downward spirals, and long, grim trances that accompany the serious gambler.

Skilled at his job, Mahowny’s given complete trust by superiors to manage customer accounts through which he secretly accesses funds for trips to Atlantic City and Las Vegas. John Hurt seems too over the top as a scheming, greedy casino executive who delights in preying upon Mahowny’s weakness in order to maximize profits, but hey, someone upstairs at Caesars must have done something bad in real life to get that casino shut down for a day. That’s not exactly a common sanction.

Minnie Driver has the thankless role of the suffering girlfriend too often accepting of the compulsive gambler’s lies and rationalizations. To make things worse for her, a wig and big glasses make her look as mousy as possible.

(Available free on YouTube. Review by Gary Rotstein.)

Rounders (1998)

Credited with helping spark the poker boom of the mid-2000s, Rounders portrays the high-stakes, underground poker scene in and around New York City at a time before the World Series of Poker exploded.

Countless poker players who sought to play the game for a living cited Rounders as raising their interest in one of America’s oldest pastimes. With a seductive sports-style narrative, Rounders features its protagonist losing his bankroll in a single heads-up poker session, thanks to an absurd bad beat with astronomical odds against occurring. He claws back some semblance of a life after vowing to quit gambling, only to soon return to the same stakes in a grudge match against the notorious card shark of the Russian-American mob.

Matt Damon’s Mike McDermott is a classic problem gambler, but his tendencies are romanticized under the depiction of poker as his calling. His final match against Teddy KGB (John Malkovich) propels him to give up law school and move to Las Vegas to compete in the WSOP, where his prospect of fortune remains for the viewer to decide.

Unlike a mentor portrayed by John Turturro, McDermott has no interest in grinding out a modest living through the game. He has his eyes set on putting it all on the line.

Rounders accurately depicts the optimism required to come back from the devastation of going broke in a poker game. The aspect of problem gambling is revealed further through Worm (Edward Norton), McDermott’s longtime, less successful poker friend who keeps depending on his buddy to bail him out of financial trouble.

While McDermott has some chance of a poker career, Worm has a life in free fall thanks to his gambling habit, which includes not just debt but a jail stint after trying to fix a local basketball game.

(Available on Netflix. Review by Brian Pempus)

Hard Eight (1996)

Paul Thomas Anderson is one of modern Hollywood’s most revered directors, and his feature debut came with this bit of gambling noir, a character study filled by some of the same actors who would populate his subsequent films.

In gambling terms, a hard eight is hitting 4-4 on the craps dice, considered a bad play, a sucker’s bet, because the house has a 9% edge if you play it. But for some reason, the film’s generally wise protagonist, the gentlemanly Sydney played by Philip Baker Hall, likes it. There’s a metaphor there somewhere, we presume.

The film revolves around the unusual interest the always-suited Sydney takes in mentoring a naive, younger man down on his luck, John (John C. Reilly, terrific like always), to navigate his way successfully through the casino worlds of Vegas and Reno. (We’re dubious about the possibility of piling up comp credit anymore at the cashier cages in the way Sydney describes. For nostalgia’s sake, however, it’s fun to see Reilly hit an old-time slot jackpot and yell, “I need a bucket! I need a bucket!” as the coins pour out.)

The older and younger man have interesting relationships with Gwyneth Paltrow as a loose cocktail waitress and Samuel L. Jackson as a coarse acquaintance, and Sydney is harboring a dark, secret background all the while.

But more than focus on plot, Hard Eight uses its undercurrent of gambling to examine the character of those attracted to it or dependent upon it for income. There’s nothing thrilling about that — nothing like hitting that hard eight at the craps table — but the writing and performances make it well worth a look.

(Available by Amazon Prime rental. Review by Gary Rotstein.)

Casino (1995)

Martin Scorsese’s Casino suffers immensely from comparisons to his mob masterpiece Goodfellas, which hit many of the same notes with some of the same cast first and better.

(Who can forget David Spade on Saturday Night Live snarking, “Casino? Ca-seen it. The first time, when it was called Goodfellas.”)

But judged on its own merits, Casino is a fun, extremely violent romp through 1970s Las Vegas, and though it’s far more focused on organized crime than on gambling, it features its share of unforgettable scenes in the titular location. Two of the most notable: Robert DeNiro’s Ace Rothstein narrating audiences through who’s watching whom on the casino floor, culminating with, “The eye in the sky is watching us all”; and Rothstein busting a couple of blackjack cheats — a gripping five-minute sequence in which we learn about “weak dealers” and why gamblers never want to find themselves in a casino’s back room.

The film is “adapted from a true story,” rather than “based on a true story,” with Rothstein inspired by Frank “Lefty” Rosenthal, who ran the Stardust, Fremont, Marina, and Hacienda casinos for the Chicago mob from the early ’70s until 1981. To keep the story simpler in Casino, Rothstein runs only the fictional Tangiers — which was “played” in the movie by the Riviera on the Las Vegas Strip.

Like the real-life Rosenthal, Rothstein (spoiler alert) ends up being run out of Vegas and spends the next phase of his career as a sports betting handicapper.

(Available by YouTube rental. Review by Eric Raskin)

California Split (1974)

A great film auteur of his era, Robert Altman, directed it.

An admitted compulsive gambler, Joseph Walsh, wrote it.

And lead actors Elliott Gould and George Segal put all of the exuberant charm they could muster into it, as a pair who meet in a California card room and wager their way through the rest of the film, all the way to a win-at-all-costs card game in Reno that includes real WSOP winner Amarillo Slim.

Though there are big losses, beatings, and bookie debts to offset some major wins, it’s a more upbeat version of a gambling pic than most on this list. Gould and Segal enjoy indulging in song and dance, and they have a memorably comic drunken moment betting $20 on whether one can name all seven dwarfs. (Spoiler alert: They fail once realizing Snoopy and Dumbo don’t fit.)

It’s interesting to see an old California card hall before Texas hold‘em was being played, and where older women made up many of the patrons. They help fill the film with some of those oddball, overlapping conversations from minor characters that are an Altman trademark.

It’s not considered one of the great Altman classics but is generally praised for the performance of the Gould-Segal team, sort of a poor man’s Newman-Redford with their handsome, sunny, impish byplay. Gould himself is known for having been into gambling big-time.

(Available by Amazon Prime rental. Review by Gary Rotstein.)

The Gambler (1974)

First things first: We’re skipping past the 2014 remake featuring Mark Wahlberg and recommending you do likewise, as no one seemed to like it, most notably James Toback.

Toback is notable because he wrote the first film, basing it on his own experiences as both a New York City College instructor and addicted gambler.

James Caan (big on attitude and sideburns of the era, with lots of low-buttoned shirts exposing chest hair) plays Axel Freed, literature professor by day, gambler by night building debts reaching $44,000 to bookies. Whenever the money to pay off the debt is within his grasp, as is sometimes the case, he … well, you know.

He explains to girlfriend Lauren Hutton and bookmaker Paul Sorvino the thing we all know for people in his shoes: It’s not about the money, it’s about the action.

“If all my bets were safe, there just wouldn’t be any juice,” Axel explains not long after one memorable scene where he’s in the bathtub late at night, listening to a buzzer-beater loss from across the country on the Lakers (Jerry West missed clutch free throws — now there’s a bad beat) before knocking the nearby radio to smithereens.

Some plot points seem unreal, like being so cocksure your $15,000 bet on a game you were leading at halftime held up that you didn’t even check the box score the next day. But hey, Caan made a pretty good living in the ‘70s out of playing cocky characters, and we didn’t live through any of this like Toback did. It’s all an effective, chilling look, regardless, at what can go wrong if you like sports betting, and start liking it wayyyy too much.

(Available by YouTube rental. Review by Gary Rotstein.)


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