© Provided by MovieWeb
We should all consider ourselves lucky that these tales didn’t stay in Vegas, as Sin City has produced some of the best and most underrated movies to ever grace the silver screen. Gambling can encompass poker and other card games, of course, but also sports betting, the lottery, and anything else of that ilk you could muster.
Most of these are set in Vegas, but that isn’t a qualification to place on the list. A few of these are in abroad casinos, and others aren’t set in gambling houses at all. Some are in more underground locations, or in other settings entirely.
One thing remains certain, though: those that made the films on this list are among the most well-known directors that Hollywood has ever had to offer. And that same could be said for several of the respective stars. All that said, though: these are the twenty greatest gambling movies of all time.
The Hangover (2009)
Kicking things off with a bit of an anomaly, The Hangover (2009) is the only clear-cut comedy movie on the entire list. Though, several other entries do feature a backdrop of humor. That said, this modern hit is in the end definitely a film of actual quality, with positive ratings from critics and even a win at the Golden Globes for Best Musical or Comedy.
And it was of course a massive success in theaters, raking in $469.3 million on a $35 million budget. It chronicles the tale of Phil, Alan, Stu, and Doug as they travel to Las Vegas for Doug’s bachelor party. And they’re all portrayed by talented thespians, most of whom shine particularly bright within comedic roles — Ed Helms, Zach Galifianakis, and Heather Graham, for example. Of course, it also features Bradley Cooper, which helped establish him as a juggernaut of the industry.
Killing Them Softly (2012)
This was lead actor Brad Pitt’s second collaboration with writer-director Andrew Dominik following their work on the revisionist western The Assassination of Jesse James by the Coward Robert Ford (2007), and their previous work together paid off here with a tangible chemistry in Killing Them Softly (2012). The project follows the aftermath of a robbery that took place within a Mafia poker game.
The heist is shown on screen, but things get interesting when Pitt’s character, a hitman named Jackie Cogan comes into play. It features back and forth, consistently well-written dialogue. And although there are some questionable choices of editing with little to write home about in the technical departments of camerawork, the overall project was definitely a success.
The Cooler (2003)
This is one of the lesser-known films on the list from a modern perspective — and that isn’t to say that The Cooler (2003) was well-received upon release with millions of dollars accrued in theaters. Its performances were revered, no doubt about that. In fact, Alec Baldwin and Maria Bello were nominated at several respectable award associations for Best Supporting Actor and Best Supporting Actress, respectively.
And those accolades are more indicative of the film’s actual quality than its acclaim from critics or number of tickets sold in theaters. William H. Macy stars as the titular character Bernie Lootz — and as a cooler in a casino, he acts as bad luck for the other gamblers, placed there by the casino themselves as a sort of negative presence. And it actually explores its characters to a meaningful extent while also showcasing the inner workings of Vegas.
Mississippi Grind (2015)
Starring Ryan Reynolds and Ben Mendelsohn, this comedy-drama was directed by American filmmaking duo Anna Boden and Ryan Fleck, and it was released by A24. It’s almost a road film of sorts, as Mendelsohn’s character — a gambling addict named Gerry — befriends Gosling’s character Curtis, and deems him a good luck charm. Thus, he recruits Curtis on a cross-country road trip to New Orleans to partake in a high-stakes poker game.
It’s dark at times, it’s touching every once in a while, and the whole way through Mississippi Grind (2015) will make you laugh at the absurdity of its characters and their many questionable decisions. The two leads develop a legitimate friendship, too, one which mirrors the chemistry of the actors themselves. If you haven’t checked this out, it’s worth it for their performances alone.
Related: Movies Ryan Reynolds Turned Down
Rounders (1998)
Directed by John Dahl, this is the only film on the list that has gone down as a true cult classic. It received lukewarm responses from critics upon release, and didn’t even double its $12 million budget when playing in theaters throughout the world. And that’s in spite of Matt Damon — fresh off his critically acclaimed screenwriting and acting efforts with Good Will Hunting (1997) — starring alongside Edward Norton, who just had an incredible string of films a few years prior, which included an Oscar-nominated performance in Primal Fear (1996).
But, again: Rounders (1998) is held in high regard today even with those initially negative numbers in mind. That is how cult classics tend to work, after all. And as the two stars play a pair of friends who travel the poker circuit attempting to pay off a debt, they build an engaging chemistry that bolsters the film’s quality through and through. It definitely holds up today.
Related: These 90s Cult Classics Still Don’t Get Enough Credit
Bugsy (1991)
With Warren Beatty in the titular role, this lauded gangster flick was led by Barry Levinson, who picked up an Oscar nomination for Best Director thanks to his efforts. That was one of ten nods received by Bugsy (1991) at the Oscars. And although Levinson came up short to Jonathan Demme for Silence of the Lambs (1991), the film as a whole picked up two wins: Best Art Direction and Best Costume Design.
For those unfamiliar with the premise: it’s set in the 1920s and follows real-life, influential Jewish mobster named Bugsy Siegel as he developed what is known today as the Las Vegas Strip. This is of course deemed by many as the entertainment capital of the world, and the primary character in the project at hand had much to do with the establishment of that moniker. It’s also a solid gambling movie, and without a doubt worth your time.
Molly’s Game (2017)
Written and directed by Aaron Sorkin, this is The Social Network (2010) of gambling films — which makes sense, as the biographical drama about the founder of Facebook was also written by Sorkin. Here with Molly’s Game (2017), though, the screenwriter took his directorial debut and chronicled the life of Molly Bloom, a former Olympic skier.
After her career was derailed by a life-changing injury to her spine, Molly was then put in charge of an underground poker game within the Viper Room in Los Angeles. The film stars Jessica Chastain in the titular role, with supporting efforts from guys like Idris Elba and Michael Cera. And all the performers delivered Sorkin’s world-famous dialogue to a critically acclaimed degree. It’s an endlessly intelligent film that will likely satisfy any gambling addicts looking for a realistic movie about poker — that’s almost entirely due to the wit of Sorkin’s script.
Ocean’s Eleven (2001)
Along with The Hangover and a select couple of others, Ocean’s Eleven (2001) by Steven Soderbergh is one of the most popular gambling movies ever made. Sure, it’s a heist film as well, but the featured location of said robbery is of course a Las Vegas casino.
The film holds an 83% approval rating on Rotten Tomatoes, and it garnered $450.7 million on an $85 million budget. That’s the greatest gross differential from any gambling movie ever released, and that commercial appeal is in large part due to its star-studded cast. George Clooney, Brad Pitt, and Matt Damon lead a supporting crew that consists of actors like Julia Roberts, Don Cheadle, Bernie Mac, Casey Affleck, and Elliot Gould. It’s easily the most well-assembled cast any gambling film has to offer, even if all its characters in the end stifle the overall pacing (and realism, for a different time) of the film itself.
Related: Best Steven Soderbergh Movies, Ranked
Uncut Gems (2019)
Written and directed by Josh and Benny Safdie, this film is perhaps best known for sparking a career resurgence for American comedy actor Adam Sandler. He received widespread acclaim for his role as Howard Ratner, a gambling addict who owns a jewelry store in the Diamond District of New York City.
And Uncut Gems (2019) as a whole made decent money in theaters — it was actually production company A24’s highest-grossing film at the time of release — on top of garnering great impressions from critics. It exudes a particularly anxiety-inducing tone to its general style of cinematography and sound design, which remains a main talking point among fans to this day. If you happened to miss this critical darling from a few years back, it’s undoubtedly worth checking out.
Casino Royale (2006)
As one of the more well-known entries of the James Bond film franchise, Casino Royale (2006) stands out much as the most action-packed project ever made about gambling. Of course, it’s also about British secret intelligence operatives and the undercover workings thereof.
This is also notable among fans today for being the first film in its franchise to feature Daniel Craig as the titular character. He would reprise the role four times, the most recent of which — No Time to Die (2021) by Cari Joji Fukunaga — marked his last appearance in the series. Fans of the films have come to adore Craig’s portrayal of the British secret agent, and that all started here with Casino Royale.
California Split (1974)
Directed by Robert Altman, this gambling saga tells the tale of its two primary characters, Bill Denny and Charlie Waters — played by George Segal and Elliot Gould, respectively. A friendship between the two blossoms after a fellow gambler gets angry at them for beating him and taking their money. So, he beats them up and the two begin gambling together.
The result is California Split (1974), a wonderful character study that delves deep into the dangers of gambling addiction. There’s no denying this entry as a classic of the gambling movie ilk, and although it hasn’t aged as well as some of its older counterparts, it will forever be remembered for its tangible tone and rock-solid narrative.
The Color of Money (1986)
This sports drama by Martin Scorsese features Paul Newman reprising his role as “Fast Eddie” Felson, who was initially established as character in The Hustler (1961), directed by Robert Rossen. More on that later, though. With regard to The Color of Money (1986): it doesn’t quite stack up to its predecessor from a critical perspective, but it was far more successful in theaters.
And a large part of that was due to its cast — aside from Newman, it also featured the likes of Tom Cruise, John Turturro, and Forest Whitaker. But it also had an intriguing premise, with Newman’s character now a retired pool hustler who takes a new gambler (Tom Cruise’s character, Vincent Lauria) under his wing. The result was an absolute pleasure of a plot that fully realizes its main players.
House of Games (1987)
Directed by David Mamet, this heist film follows Lindsay Crouse’s character Dr. Margaret Ford as she meets a criminal figure named Mike Mancuso — played wonderfully by Joe Mantegna. She’s a psychiatrist who recently finished a book on obsessive-compulsive disorder, and one of her patients seeks help from her regarding his involvement with and debt owed to the aforementioned crime lord.
So, again, she meets him at the fictional pool hall from which the film derived its title: House of Games (1987). Dr. Ford develops a meaningful relationship with Mike after she catches him attempting to con her, and the two experience the downfalls of gambling like few other characters on this list. It’s a truly gripping tale, and one that absolutely holds up all these years later.
Related: 10 Underrated Crime Films of the 1980s
The Sting (1973)
With seven wins at the Academy Awards out of ten total nominations, The Sting (1973) is perhaps the most acclaimed film of the entire list. It also holds a 92% approval rating on Rotten Tomatoes, and has been selected by the Library of Congress for preservation in the National Film Registry. And one could argue that the bulk of its admiration from fans and critics alike stemmed from the chemistry of its cast.
Which makes sense, as lead actors Paul Newman and Robert Redford had previously worked with director George Roy Hill on Butch Cassidy and the Sundance Kid (1969). The performers share a tangible chemistry with the filmmaker, and that dynamic pops out through the screen of every featured frame. Its story of two professional grifters who team up to con a mob boss and avenge the death of their mutual friend. It holds up in every was imaginable, and lands here at number seven.
The Gambler (1974)
As far as true gambling addiction goes, James Caan’s titular character in The Gambler (1974) portrays the mental illness better than perhaps anyone in the history of the silver screen. He’ll bet good money on a poker game in Las Vegas, on a professional football championship with his friends, or on a pickup game of basketball he stumbled upon during his afternoon stroll through the park.
Axel Freed is also a writer and an English teacher, but again: his true passion lies with gambling in this crime film, and his portrayal by Caan was widely revered. In fact, the famous American actor received his second nomination at the Golden Globes for his performance herein, and really carried the film on his back in a lot of respects. It should truly be remembered as one of his best roles, and one of the best gambling movies ever made.
The Cincinnati Kid (1965)
Directed by Norman Jewison, many hardcore film fans would cite this as the greatest gambling movie, period. Its pacing hasn’t aged as gracefully as others on this list, though. And while director Norman Jewison didn’t top the list with The Cincinnati Kid (1965), the number five spot is nothing to complain about. He still played a winning hand.
Steve McQueen stars herein as Eric “The Kid” Stoner, an up-and-coming poker player in New Orleans. It’s set during The Great Depression, and chronicles The Kid’s journey as he challenges a veteran card player in Lancey “The Man” Howard — played by Edward G. Robinson. The script brims with wit until the final hand is dealt, and the poker players themselves are portrayed wonderfully by each respective performer. There’s a reason it’s still so revered.
Croupier (1998)
What’s worth noting off the bat about this project is its utilization of interior monologues to emulate the neo-noir or detective style of film that screenwriter Paul Mayersburg and director Mike Hodges drew inspiration from. But Croupier (1998) also provides great insight into the ins and outs of casino work, with technical jargon around every corner of the British gambling house in which the film is set.
And what materializes from its slick style and intelligent script is a career-defining performance from English actor Clive Owen that dives deep into the intricate nature of the human condition. Its compelling plot becomes a character study of sorts, and Jack Manfred should by dint of that go down as the single most compelling protagonist to ever be featured in a gambling movie. And that’s hardly scratching the surface of what makes Croupier so great.
Hard Eight (1996)
If this list were ranking the most underrated gambling movies ever made, Hard Eight (1996) by Paul Thomas Anderson would undoubtedly come out on top. It stars Phillip Baker Hall along with a star-studded supporting cast of John C. Reilly, Gwyneth Paltrow, Samuel L. Jackson, and Phillip Seymour Hoffman, and they all play a meaningful role in the wide-ranging plot. Except for Hoffman, that is — although, his one scene in the film almost managed to steal the entire show.
The film follows Hall’s character Sydney as he takes Reilly’s character John under his wing and shows him the ropes of professional gambling in Las Vegas. There, John meets and falls in love with a waitress named Clementine (played by Paltrow), and the plot develops into sort of a crime thriller as the trio find themselves in deep within an unfortunate situation that could lead to plenty of jail time for all three.
The Hustler (1961)
Along with The Sting, this is the other film on the list that almost transcends the gambling ilk from a sheerly critical perspective. Directed by Robert Rossen and starring Paul Newman as “Fast Eddie” Felson, this is of course the film that sparked Scorsese and crew to create The Color of Money. And although that film was well-acclaimed in itself, The Hustler (1961) has almost gone down as a classic.
It won two of its nine nominations at the 34th Academy Awards, and has since been selected by the Library of Congress for preservation in the National Film Registry. And as Fast Eddie seeks to test his pool hustling aptitude against the professional player “Minnesota Flats”, the stars of this sports show in Newman and George C. Scott lead the project to utter greatness. There’s a reason it’s garnered such acclaim.
Casino (1995)
This is pretty much a gambling epic, like a sprawling western directed by Sergio Leone or Howard Hawks with Robert De Niro playing the gunslinging head of the titular location in Casino (1995). And in this case, the epic was directed by Martin Scorsese in one of his most ambitious films to-date.
It had a similar narrative to Scorsese’s other Mafia movies like Mean Streets (1973) and Goodfellas (1990), but wasn’t quite as revered as those two were upon release. Its performances were, though, particularly from Joe Pesci and Sharon Stone — the latter of whom was nominated for Best Actress at the Academy Awards, and won in the same category at the Golden Globes. Everyone in Casino performed to a career-defining degree, and it will forever go down as one of Scorsese’s bests.