Given that Sin City has given birth to some of the greatest and most underappreciated films to ever grace the silver screen, we should all consider it a blessing that these stories didn’t stay in Vegas. Poker and other card games fall under the category of gambling, but it also includes other games like the lottery, sports betting, and everything else you can think of.
Although the majority of these are set in Vegas, that does not automatically qualify them for inclusion. Some of these are set in foreign casinos, while others have nothing to do with casinos at all. Some are altogether in other environments or in regions that are farther underground.
Yet one thing is certain: the filmmakers behind the movies on this list are among the most renowned ones Hollywood has ever produced. And several of the stars in question could be said to fit this description. Having said that, these are the top twenty gambling films of all time.
Bugsy (1991)
This acclaimed gangster movie starred Warren Beatty in the title role, and Barry Levinson directed it. For his work, he received an Oscar nomination for Best Director. That was one of Bugsy (1991)’s ten Oscar nominations. Levinson lost out to Jonathan Demme for the 1991 film Silence of the Lambs, but the movie as a whole won two awards: Best Art Direction and Best Costume Design.
For those who are not familiar, it is based on the actual life of renowned Jewish mobster Bugsy Siegel, and it takes place in the 1920s as he created what is now the Las Vegas Strip. Naturally, this is widely regarded as the “Entertainment Capital of the World,” and the main character in the current project had a significant role in its development. It’s a good gambling movie as well, and it’s definitely worth your time.
California Split (1974)
The two main protagonists in this gambling adventure, Bill Denny and Charlie Waters, who are alternately portrayed by George Segal and Elliot Gould, are the focus of Robert Altman’s direction. Once one of the other gamblers gets upset with them for beating him and stealing their money, a friendship between the two develops. So after beating them up, the two start playing poker together.
California Split (1974), a superb character study that explores the risks of gambling addiction, is the outcome. There is no doubting that this film is a classic in the genre of gambling movies. Although not having aged as well as some of its older contemporaries, it will always be recognised for its realistic tone and compelling story.
Casino (1995)
This is essentially a gambling epic, similar to a vast Sergio Leone or Howard Hawks western with Robert De Niro portraying the gunslinging boss of the namesake establishment in Casino (1995). Martin Scorsese helmed the epic in this case, one of his most ambitious movies to date.
It shared a similar plot with Scorsese’s earlier Mafia films, such as Mean Streets (1973) and Goodfellas (1990), although it wasn’t as well-received when it first came out. But, it was Joe Pesci and Sharon Stone who stood out for their performances, with the latter earning both a Golden Globe and an Academy Award nomination for Best Actress. Casino will always be remembered as one of Scorsese’s best films since everyone in it gave performances that defined their careers.
Casino Royale (2006)
Casino Royale (2006), one of the more well-known films in the James Bond series, stands out as the most action-packed gambling-related production ever done. Of course, it also pertains to British secret intelligence agents and their covert operations.
The fact that Daniel Craig played the title role in this movie for the first time makes it significant among fans today. His final appearance in the series was in No Time to Die (2021), which was the most recent of his four reprises of the part. Craig’s portrayal of the British secret agent has become beloved by moviegoers, and it all began with Casino Royale.
Croupier (1998)
It’s important to note right away how this project uses private monologues to mimic the neo-noir or detective cinema genres that writer Paul Mayersburg and director Mike Hodges were inspired by. Yet, Croupier (1998) also offers valuable insight into the ins and outs of casino work, with technical language present in every room of the fictional British gambling establishment.
A career-defining performance from English actor Clive Owen that delves deeply into the complex essence of the human condition results from the film’s polished aesthetic and sharp narrative. Jack Manfred should, as a result of that, go down as the single most captivating protagonist to ever be featured in a gambling movie because of how its compelling plot turns into a character study. And even that is just the tip of what makes Croupier so outstanding.
Hard Eight (1996)
Hard Eight (1996) by Paul Thomas Anderson would unquestionably be at the top of our list if it were listing the most underappreciated gambling movies ever created. Along with John C. Reilly, Gwyneth Paltrow, Samuel L. Jackson, and Phillip Seymour Hoffman, who all have significant roles in the complex plot, the film also stars Phillip Baker Hall. Hoffman is the exception, despite the fact that his single part in the movie nearly managed to steal the entire show.
The movie follows Sydney, a character played by Hall, as he mentors John, a character played by Reilly, and teaches him the fundamentals of Las Vegas’s professional gambling industry. There, John meets and falls in love with Clementine, a waitress played by Paltrow, and the plot turns somewhat into a crime thriller as the trio finds themselves embroiled in an unpleasant circumstance that could result in lengthy jail terms for all three.
House of Games (1987)
This heist movie, which was directed by David Mamet, centres on Lindsay Crouse’s Dr. Margaret Ford when she encounters Joe Mantegna’s menacing character Mike Mancuso. One of her patients seeks her assistance regarding his relationship with and debt owed to the aforementioned criminal boss. She is a psychiatrist who recently published a book on obsessive-compulsive disorder.
So once more, she runs into him at the imaginary pool hall that gave the movie its name: House of Games (1987). After she catches Mike trying to swindle her, Dr. Ford and Mike form a close bond and are among the few characters on this list who actually feel the drawbacks of gambling. It’s a really compelling story that still stands up today, even after all these years.
Killing Them Softly (2012)
Following their work on the revisionist western The Assassination of Jesse James by the Coward Robert Ford (2007), writer-director Andrew Dominik and star Brad Pitt collaborated again, and their prior work together paid off with a palpable connection in Killing Them Softly (2012). The project explores the events that followed a heist that occurred during a Mafia poker game.
The theft is portrayed on film, but the action really picks off when Pitt’s hitman Jackie Cogan enters the picture. It has back-and-forth dialogue that is consistently well-written. The whole effort was unquestionably successful, despite some dubious editing decisions and unremarkable camerawork in the technical sectors.
Mississippi Grind (2015)
This comedy-drama, which starred Ryan Reynolds and Ben Mendelsohn, was made by American filmmakers Anna Boden and Ryan Fleck and distributed by A24. Mendelsohn’s character, a gambling addict named Gerry, befriends Ryan Gosling’s character Curtis and views him as a good luck charm in what is essentially a road movie. He then enlists Curtis to accompany him on a cross-country road trip to New Orleans so that they can play high-stakes poker.
Mississippi Grind (2015; gloomy at times, touching occasionally) will make you giggle throughout at the absurdity of its characters and their numerous dubious choices. The two leads also have a sincere friendship that reflects the compatibility of the performers. It’s worth it just to watch their performances if you haven’t before.
Molly’s Game (2017)
This is the The Social Network (2010) of gambling movies; it was written and directed by Aaron Sorkin, which makes sense given that Sorkin also wrote the biographical drama about the creator of Facebook. But in Molly’s Game (2017), the screenwriter made his directorial debut and followed the life of former Olympian skier Molly Bloom.
In control of an underground poker game within the Viper Room in Los Angeles after her career was wrecked by a life-altering spinal injury. Jessica Chastain plays the title role in the movie, and Idris Elba and Michael Cera provide supporting performances. And each performer did a highly praised job of delivering Sorkin’s renowned dialogue. The wit of Sorkin’s script is almost entirely to blame for this endlessly brilliant movie’s ability to gratify any gamblers seeking a realistic poker movie.
Ocean’s Eleven (2001)
One of the most well-known gambling movies ever produced is Ocean’s Eleven (2001), directed by Steven Soderbergh, along with The Hangover and a select few others. Indeed, there is a heist movie as well, but the main setting for the robbery is undoubtedly a Las Vegas casino.
On Rotten Tomatoes, the movie had an 83% approval rating and made $450.7 million against a $85 million budget. The biggest gross differential of any gambling film ever made, and a huge portion of its commercial success can be attributed to its all-star cast. Leading the supporting cast are George Clooney, Brad Pitt, and Matt Damon, together with Julia Roberts, Don Cheadle, Bernie Mac, Casey Affleck, and Elliot Gould. Even though all of its characters ultimately slow down the overall speed (and realism, for a different period), it is unquestionably the best cast any gambling film has to offer.
Rounders (1998)
This is the only movie on the list that has established itself as a genuine cult classic, and it was directed by John Dahl. When it was first released, it earned mixed reviews from reviewers and failed to recoup even half of its $12 million production cost in theatres around the globe. And that’s in spite of Edward Norton, who recently had an incredible string of movies just a few years prior, including an Oscar-nominated performance in Primal Fear, costarring with Matt Damon, who had just come off of his critically acclaimed screenwriting and acting efforts with Good Will Hunting (1997). (1996).
But once more, despite those first poor ratings, Rounders (1998) is now regarded highly. After all, cult classics frequently function in this way. The two actors develop a compelling chemistry as they portray a couple of pals who cruise the poker circuit in an effort to pay off a debt. This raises the overall quality of the movie. Definitely still relevant now.
The Cincinnati Kid (1965)
Many die-hard movie buffs would consider this, which was directed by Norman Jewison, to be the best gambling movie ever made. Its tempo, though, hasn’t aged as well as some of the others on this list. The Cincinnati Kid (1965), directed by Norman Jewison, didn’t top the list, but the fifth place isn’t bad either. He continued to play a strong hand.
Here, Steve McQueen plays Eric “The Kid” Stoner, a rising poker star from New Orleans. The story, which takes place during the Great Depression, follows The Kid as he competes against Edward G. Robinson’s seasoned card player Lancey “The Man” Howard. The actors do a fantastic job at portraying the poker players, and the screenplay is hilarious all the way through the last card is dealt. It is still regarded with such awe for a reason.
The Color of Money (1986)
Paul Newman reprises his role as “Fast Eddie” Felson, who was first introduced in Robert Rossen’s 1961 sports drama The Hustler, in this Martin Scorsese production. But more on that later. From a critical standpoint, The Color of Money (1986) doesn’t quite measure up to its predecessor, but it was a much bigger hit at the box office.
And a big part of that was because of its cast, which included actors like Tom Cruise, John Turturro, and Forest Whitaker in addition to Newman. It also featured an unusual storyline, with Paul Newman’s former pool hustler taking under his wing Vincent Lauria, a new gambler played by Tom Cruise. The end result was a plot that fully realised its primary characters, which was an amazing delight.
The Cooler (2003)
From a contemporary perspective, The Cooler (2003) is among the less well-known movies on the list, but that doesn’t mean it wasn’t warmly received when it was first released and made millions of dollars in theatres. Without a doubt, its performances were admired. Alec Baldwin and Maria Bello were actually nominated for Best Supporting Actor and Best Supporting Actress, respectively, at a number of reputable award organisations.
And such plaudits speak more to the movie’s true quality than critics’ praise or the quantity of tickets that were bought at the box office. As the title character Bernie Lootz, played by William H. Macy, he acts as bad luck for the other gamblers, having been placed there by the casino as a sort of unfavourable presence. Also, it shows the inner workings of Vegas while meaningfully examining its characters.
The Gambler (1974)
The Gambler (1974), starring James Caan as the title character, is arguably the greatest example of a serious gambling addiction ever shown on film. He’ll wager a sizable sum of money on a poker game in Las Vegas, a professional football game with friends, or a pickup basketball game he happens to come across while taking a stroll through the park in the afternoon.
In this crime movie, Axel Freed is also a writer and an English teacher, but once again, his true passion is gambling, and Caan’s portrayal of him received high praise. In fact, the well-known American actor won his second Golden Globe nomination for this performance, and in many ways, he carried the entire movie on his shoulders. One of his best performances and one of the greatest movies about gambling ever made should both be remembered.
The Hangover (2009)
The Hangover (2009) is the only unmistakably comedic film on the entire list, so that’s a bit of an oddball to start things off with. Nonetheless, a few other entries do have humorous backgrounds. Despite this, this contemporary smash is ultimately unquestionably a high-caliber movie, receiving favourable reviews from reviewers and even taking home the Golden Globe for Best Musical or Comedy.
Naturally, it was a huge hit in theatres, grossing $469.3 million on a $35 million budget. It tells the story of Doug’s bachelor celebration in Las Vegas and follows Phil, Alan, Stu, and Doug on their journey there. And all of them are played by accomplished actors, many of whom excel in comedic roles – Ed Helms, Zach Galifianakis, and Heather Graham, to name a few. Naturally, Bradley Cooper is also a part of it, helping to make him a household name in the business.
The Hustler (1961)
This is the second movie on the list, after The Sting, that virtually surpasses the genre of gambling from a purely analytical standpoint. Of course, this is the movie that inspired Scorsese and his team to make The Color of Money, which was also directed by Robert Rossen and starred Paul Newman as “Fast Eddie” Felson. The Hustler (1961), despite the fact that it was a successful movie in its own right, is virtually considered a classic.
During the 34th Academy Awards, it received two wins out of the nine nominations it received, and the Library of Congress has since chosen it for preservation in the National Film Registry. And the stars of this sports programme, Newman and George C. Scott, drive the project to absolute greatness as Fast Eddie attempts to test his pool hustle skills against the professional player “Minnesota Flats.” There’s a reason why it’s received so much praise.
The Sting (1973)
The Sting (1973) is arguably the most well-regarded movie on the list, having received seven Academy Award victories out of a total of ten nominations. Also, it has a 92% approval rating on Rotten Tomatoes and has been chosen for inclusion in the National Film Registry by the Library of Congress. Yet one can contend that the cast’s chemistry was largely responsible for its acclaim from both critics and fans.
It makes sense considering that Butch Cassidy and the Sundance Kid director George Roy Hill previously collaborated with key stars Paul Newman and Robert Redford (1969). Every featured frame vividly displays the on-screen relationship that exists between the actors and the director. It tells the tale of two seasoned crooks who get up to scam a mob leader and exact revenge for the murder of a comrade they both shared. It ranks here at number seven and holds up in every way imaginable.
Uncut Gems (2019)
This movie, which was written and directed by Josh and Benny Safdie, is best known for having given American comedian actor Adam Sandler a new lease on life. He won a lot of praise for his portrayal of Howard Ratner, a gambling addict who runs a jewellery shop in New York City’s Diamond District.
In addition to receiving positive reviews from critics, Uncut Gems (2019) grossed a respectable amount of money at the box office and was the highest-grossing movie ever created by the production firm A24 at the time of release. Its whole cinematography and sound design emanate a particularly anxiety-inducing tone, which is still a major talking point among fans today. It’s definitely worth seeing out if you happened to miss this critical darling from a few years back.
