The 15 Best Gambling Movies Of All Time, Ranked – SlashFilm

Movies about gambling follow a simple mantra: A character or characters go up against the odds, eschewing safe bets for a risky, life-changing move. The stakes are high, but the rewards are plentiful. Our protagonists encounter numerous obstacles during their journey and often incur severe losses. They almost always experience a moment of self-reflection and are faced with the ultimate choice: go all in or fold. Rinse and repeat.

Hundreds of movies about gambling exist to tell this same story time and again, with slight variations on the formula. Audiences turn up in droves to watch these powerful morality tales play out on the silver screen. And why not? The gambling genre presents the hero’s journey in its purest form. It’s the quintessential underdog tale, except rather than score the final shot in the big game, characters risk life and limb for a chance to beat the house, upend the establishment, as it were.

But which film is the best?

Whether you’re new to the sub-genre or merely looking for an old-fashioned hustling flick set within the world of Las Vegas, underground poker, or at the race track, we’ve got you covered with a list of the 15 best gambling movies of all time, ranked from good to great. Read ’em and weep!

The most no-frills entry on this list, “Lucky You,” uses the World Series of Poker as a backdrop for a story about fathers and sons, with a love story featuring Drew Barrymore tossed in for good measure. And it works — mostly.

Huck Cheever (Eric Bana) is a professional poker player forced to confront his past after his estranged poker-playing father, L.C. (Robert Duvall), appears, looking to amend their relationship. Also on the table is Billie (Barrymore), a plucky singer on the rise who gets entangled in Huck’s gambling exploits. It all comes down to a showdown between father and son on the world’s largest stage, the World Series of Poker. And while the emotional finale may feel like familiar Hollywood hokum, somehow, director Curtis Hanson, working from a screenplay by Eric Roth, brings it all together for a satisfying, even warmhearted, conclusion. 

Moreover, the film is a fine starting point for anyone yearning to learn more about poker. Numerous scenes are devoted to people explaining the basics of the game, ensuring that attentive viewers will walk away with a better understanding of the sport.  

Likely the lowest-rated film on this list with a meager 30% on Rotten Tomatoes, “Let It Ride” is nonetheless a bouncy, silly film starring Richard Dreyfuss as a former gambling junkie who gets lured back to the race track, where he enjoys a streak of incredible luck. Directed by Joe Pytka, “Let It Ride” managed just $4.9 million when it rolled into theaters in August 1989 amidst stiff competition and has largely flown under the radar.

That’s too bad, because Dreyfuss has an absolute blast playing Jay Trotter, a manic bundle of nervous energy hidden beneath a relatively calm demeanor. He perfectly captures the indescribable highs and lows every gambler feels during those brief but pivotal moments when they bet the farm for a chance at immortality. The picture has fun poking at familiar tropes, culminating in a hilarious sequence in which various characters make lofty promises to the gods in exchange for a win. “Let It Ride” caters to a very niche audience that understands and empathizes with the madness on display. Don’t listen to critics, this one’s a winner.    

In Las Vegas, you’re either a winner or a loser. William “Bernie” Lootz (William H. Macy) is the latter, at least at the outset of Wayne Kramer’s “The Cooler,” but through the power of love, his cold streak turns into a jackpot.

William “Bernie” Lootz is a professional “cooler” who gets paid to rub his bad luck onto other people, specifically those playing in a casino run by Sheldon “Shelly” Kaplow (Alec Baldwin). Situations change when Bernie falls for a cocktail waitress named Natalie (Maria Bello), a relationship that quickly snaps him out of his funk and brings good fortune. The chips begin to pile up when Bernie’s estranged son Mikey (Shawn Hatosy) appears and tries to cheat Shelly’s casino, requiring Bernie to shake his lousy luck once and for all and win back the money or wind up sitting at the loser’s table for life.

“The Cooler” is a damned fine film with sharp performances, particularly by Baldwin, who earned an Academy Award nomination for his part. It isn’t flashy and ends on a shockingly positive note, but even Vegas can deal a lucky winner every now and then.

Another delectable treat from famed writer (and director) Aaron Sorkin, “Molly’s Game,” follows Molly Bloom (Jessica Chastain) as she navigates the treacherous world of high-stakes underground poker. A former professional skier who crashed and burned during a qualifying round that would have sent her to the Olympics, Molly takes a job as an office manager for a real estate developer and soon begins managing his lucrative poker matches between A-list celebrities, politicians, and other high-ranking officials. Eventually, she sets out on her own and creates a hotspot that draws the biggest names, and lands her buckets of fortune.

Of course, all good things must come to an end. The Russian mafia begins participating in Molly’s games, drawing interest from the FBI; she becomes addicted to drugs and is later connected to a well-publicized Ponzi scheme — in other words, its your typical boom and bust tale.

Except, “Molly’s Game” rises above similar offerings thanks to Sorkin’s sharp script and Chastain’s performance, which our own Chris Evangelista described as “dynamite” in his review. Additionally, everything we’re watching actually transpired in real life, right down to Molly’s complicated relationship with her overbearing father (Kevin Costner). No, really, go read Molly’s wild, true story, then try to look at Tobey Maguire the same way again.

A list of gambling movie greats must include Barry Levinson’s “Bugsy,” the true story about the man who literally created Sin City. Starring Warren Beatty and Annette Bening, the 1991 Oscar-winning drama chronicles prominent gangster Benjamin “Bugsy” Siegel’s attempts to turn an empty desert locale into a budding gambling enterprise, i.e. Las Vegas, an endeavor that ultimately costs him his life.

Levinson and writer James Toback take plenty of historical liberties recounting Bugsy’s life, morphing him from a cold blooded killer to a tragic character undone by ambition. Even so, the film does a bang-up job recreating the era and depicting the machinations behind the formation of the Flamingo Hotel that served as the cornerstone for present-day Las Vegas. Levinson also takes a look at the ties between early Hollywood and the mob, and Bugsy’s chaotic relationship with Virginia Hill. It’s undoubtedly a more romanticized version of the gangster’s life and a sensational piece of Hollywood-ized entertainment, but the filmmakers capture the gist of the real tale.

Beatty is great as Bugsy, portraying him as a man with dreams, undone by poor decisions and a wicked temper, while Bening brings a novel complexity to Virginia Hill. “Bugsy” may not always pass the history test, but it succinctly captures the life of a man who dreamed big and fell hard. 

Martin Scorsese’s lavish sequel to the 1961 Oscar-winning classic “The Hustler” finds a much older “Fast Eddie” Felson (Paul Newman) grappling with his legacy and taking Vincent Lauria (Tom Cruise), a young, hotshot pool player, under his wing. Initially successful in hustling other pool players for money, Eddie and Vincent’s relationship sours when the latter’s ego gets in the way, prompting Eddie to challenge his young apprentice to a no-holds-bar match.  

“The Color of Money” provides an exceptional showcase for Newman and Cruise’s acting abilities, and the duo is sensational in their respective roles, with the latter bringing the same swag and vigor displayed in early efforts like “Top Gun” and “Rain Man.” It’s crazy that it took a last-second intervention from Disney to get the guaranteed hit produced. Scorsese and cinematographer Michael Ballhaus shoot the hell out of the picture and seem to find creative new ways to capture the ferocity of billiards. “Color of Money” looks fantastic, and while it may not move with the same ferocity as Scorsese’s notable works, it fulfills as a story about redemption, loyalty, betrayal, and friendship.

Does “Color of Money” top the moral complexity of “The Hustler”? That’s debatable. Still, Scorsese finds exciting ways to challenge Eddie, pushing the icon to the brink until he decides, once and for all, “I’m back!”

Breezy fun, Richard Donner’s “Maverick” might as well be a sequel (or prequel) to “Lethal Weapon,” what with its screwball humor, exhilarating set pieces, and hilarious back-and-forth dialogue between the leads. Rather than Mel Gibson, Danny Glover, and Joe Pesci, however, “Maverick” gives us Gibson, Jodie Foster, and James Garner (who starred on the television series on which the film is based), and, as one character notes, “It’s a whole lotta fun.”

Bret Maverick (Gibson) is en route to a high-stakes poker contest that costs $25,000 to enter. He’s $3,000 short and must travel the old West collecting debts from friends and enemies. During his trip, he meets up with the lovely Annabelle Bransford (Foster) and straight-shooting Marshal Zane Cooper (Garner), forming an improbable trio that must band together to contend with Native Americans, malcontent Russians, drunken thieves, and a tough-as-nails cowboy named Angel (Alfred Molina) trying to prevent our hero from making the game.

“Maverick” is probably too long by about 20 minutes and often at odds with itself. Donner can’t decide if he’s making an epic Western or a silly comedy. Still, this adventure is worth taking if you love stars like Gibson and Foster.

Slickly designed, Steven Soderbergh’s “Ocean’s Eleven” understands the assignment. Rather than bore audiences with another plot about criminals going after a final score, this remake of 1960’s “Ocean’s Eleven” contently devotes more time to the back-and-forth banter between its star-studded cast than on the heist itself. Like “Maverick,” this is a movie about good-looking people doing cool things. Like flies on the wall of an A-plus Hollywood party, we need only kick back and watch George Clooney, Julia Roberts, Matt Damon, and Brad Pitt do their thing.

The plot, for what it’s worth, concerns a recently released convict named Danny Ocean (Clooney), who devises a plan to rob three Las Vegas casinos — the Bellagio, the Mirage, and the MGM Grand. Doing so requires cons upon cons, forcing Danny to assemble a crackerjack team of crooks. Enter Ocean’s Eleven, comprised of all-stars Pitt, Damon, Bernie Mac, Elliot Gould, Casey Affleck, Scott Caan, Eddie Jemison, Don Cheadle, Qin Shaobo, and Carl Reiner, all of whom do their part to bring down the house.

Soderbergh takes a low key approach to the material, preferring to let his stars carry the heavy load. Sure, moments of intensity pop up now and again, particularly during the third-act heist, and a few twists and turns stir our interest. Really, though, like its sequels, “Ocean’s Twelve” and “Ocean’s Thirteen,” “Ocean’s Eleven” is all about the talent. To that end, it’s an enormously entertaining ride. Now, can the gang please return for “Ocean’s Fourteen”?

Leave it to Robert Altman to produce an all-timer in the gambling movie genre. Many consider “California Split” a novel entry on this list, and they’re not wrong. Working from a script by Joseph Walsh, Altman crafts a naturalistic character picture about two gambling buddies, Bill Denny (George Segal) and Charlie Waters (Elliot Gould), and their tumultuous run for fame and fortune.

Bill works an average job at a magazine but quickly succumbs to the electric lifestyle presented by the likes of poker, blackjack, craps, and roulette. The more he wins, the deeper he goes, resulting in a rags-to-riches-to-rags tale that questions the psychological impact of gambling.

At turns funny and dramatic, “California Split” failed to connect with audiences in 1974, despite lavish praise from critics like Kevin Kelly of the Boston Globe, who wrote: “‘California Split’ is a work of art and Robert Altman’s best movie.” That reaction may be a tad hyperbolic. Still, this gambling dramedy contains every one of the legendary director’s trademarks — overlapping dialogue, an ambling narrative, and a raw look and feel that really makes you believe you’re watching a couple of guys fighting to stay alive in a dangerous world.

It’s so good, /Film’s Ben Pearson recommended it on his Quarantine Stream.

Before making waves with 1997’s “Boogie Nights,” Paul Thomas Anderson directed “Hard Eight,” a moody character piece about an aged gambler named Sydney Brown (Philip Baker Hall) who takes a homeless man named John Finnegan (John C. Reilly) under his wing and teaches him the ins and outs of Las Vegas. Emerging as a fatherly figure for John, Sydney tries to connect his protege with Clementine (Gwyneth Paltrow), a young cocktail waitress and prostitute, and winds up ruffling the feathers of a security worker named Jimmy (Samuel L. Jackson).

Quiet, reflective, and jam-packed with slick performances, this stylish feature doesn’t go for big theatrics. Instead, Anderson keeps his eye on his collection of mismatched characters. We watch them speak in hushed tones in dimly lit hotel rooms and casinos, and take lofty chances on the casino floor in search of a higher purpose. At times, “Hard Eight” feels more like a day in the life of Sydney Brown. You won’t walk away with a deeper understanding of life, but you may identify with these unique individuals on a personal level. At the very least, you’ll learn how to finagle a casino for a free room.

Less a movie about gambling than a movie about the people operating the gambling scene, Martin Scorsese’s “Casino” nonetheless does a remarkable job showing the rise and fall of the Las Vegas mob as seen through the eyes of Sam “Ace” Rothstein (Robert De Niro). As with any crime drama directed by the maestro, “Casino” pulls no punches, showing the abhorrent activities – drugs, sex, murder — of these lifelong criminals and their free fall from the top of the world into utter darkness. Remarkably, through it all, we admire, even pity, Ace and root for him to succeed against his adversaries, including violent friend-turned-foe Nicky Santoro (Joe Pesci).

And why not? The man shoots straight and dreams of turning Vegas into a massive empire. He successfully conjures a plethora of cash for his Chicago bosses, and transforms his casino into a literal paradise. Unfortunately, his problematic relationship with Ginger McKenna (Sharon Stone), a con artist and showgirl, proves too chaotic to overcome, as does the presence of the volatile Nicky. Together, the trio destroy the vast empire they fought so hard to create, one brick at a time. 

“Casino” is a stylish exploration of power, betrayal and moral decay. It’s a tough to watch, but it encapsulates the spirit of Vegas, where success is futile and the house always wins.  

In the early days of his budding career, just a year after “Good Will Hunting” shot him to superstardom, Matt Damon starred in “Rounders,” a low-budget drama from John Dahl about underground poker, and crafted one of his most memorable roles. While straying closer to fantasy, this impressive 1998 picture dives deep into the world of poker, following a former grifter named Mike McDermott (Damon) as he struggles to cast aside his dark past in favor of a more routine lifestyle with his girlfriend Jo (Gretchen Mol).

Everything changes when Mike’s longtime pal, Lester “Worm” Murphy (Edward Norton), recently released from prison, suddenly appears in dire need of assistance. It seems Worm has accrued massive debt, forcing Mike to come out of retirement to help his friend. As tensions mount, Mike’s loyalties are tested, and his relationship with Jo is pushed to the brink. Everything builds toward a sensational showdown with an Oreo-chomping Russian mobster named Teddy “KGB” (John Malkovich). Will Mike win the money required to keep him and Worm alive? Will he ever find happiness outside the poker scene?

“Rounders” is more Hollywood fable than many films on this list, but it’s undeniably entertaining, well-acted, and directed. Heck, it almost got a sequel. It makes you want to hop in the car, drive to Vegas, and put it all on the line. “Pay that man his money!”

A delightful comedy-drama from George Roy Hill, “The Sting” features superstars Paul Newman and Robert Redford as grifters who team up to hustle Robert Shaw’s violent Irish-American crime boss. Utilizing a hefty dose of ragtime, notably Scott Joplin’s “The Entertainer,” this 1973 crowd pleaser grossed a then massive $159 million at the box office and won seven Oscars, including best picture, best director, best film editing, and best original screenplay.

Set in 1936 during the height of the Great Depression, “The Sting” sees small-time grifter Johnny Hooker (Redford) accidentally steal money from notorious gangster Doyle Lonnegan (Shaw), a costly mistake that leaves his best friend dead. Looking to avenge his partner, Hooker befriends Henry Gondorff (Newman, who, believe it or not, almost didn’t star in the film), and together they plan “the big con” aimed at taking down Lonnegan for good.

Much like Hill, Newman, and Redford’s previous collaboration, the equally famous “Butch Cassidy and the Sundance Kid,” “The Sting” bounces back and forth between light-hearted comedy and gritty drama, leaving audiences laughing while occasionally gripping the edge of their seats. It’s a fabulous piece of old-fashioned entertainment featuring numerous classic scenes, notably a card game aboard a train between Lonnegan and a pretending-to-be-drunk Gondorff — an exceptional moment between two Hollywood legends.  

Adam Sandler delivers an ace performance in Benny and Josh Safdie’s “Uncut Gems,” a gripping character study about a man addicted to high-stakes sports betting. Filmed in a manner guaranteed to increase heart rates, this splendid A24 production shows the highs and lows of the gambling industry, where a person will do anything to taste success.

Divorced and deep in debt, Howard Ratner (Sandler) can never seem to find happiness beyond his degenerate gambling lifestyle. He places outrageous parlays on specific sports stars — in this case, Kevin Garnett, who enjoys a prominent role in the film — and takes bold risks with other people’s money despite recurring physical punishment. A bit of luck allows Howard to acquire a 600-carat black opal from Ethiopia that he believes is worth over $1 million. However, when an auction dealer prices the opal under $200K, Howard, rather than pay off his debts, goes all in on another parlay that could rain fortune or pave a path to self-destruction.

Few films capture the same raw intensity as this masterful gem. Sandler’s performance is a sight to see. Look for a secret cameo from Tilda Swinton.

If you were going to watch a single film about gambling, 1974’s “The Gambler” checks all the necessary boxes. Here, we have English professor Axel Freed (a magnificent James Caan), who moonlights as a gambling addict, much to the chagrin of those around him, including his mother (Jacqueline Brookes) and girlfriend (Lauren Hutton). Despite his privileged upbringing, Axel only experiences true exhilaration through risky bets that seldom pay off. This reckless behavior destroys his relationships with friends and colleagues, eventually forcing him to make a final, high-stakes gamble that leaves his life hanging in the balance.

Wonderfully acted and directed, “The Gambler” is a profound and realistic tale of self-destruction. Uniquely, the film presents Axel as a successful man with a good job and a relatively good life, a safety net he’s willing to throw away for a little “juice.” Every film on this list leans on similar tropes, but “The Gambler” does it best, crafting a powerful, even harrowing tale that expertly conveys the pitfalls of living life on the edge.

Just be sure to avoid the pitiful 2014 remake.