Barb’s Best Bets: Top 10 Gambling Movies That You Must See

Updated on October 16, 2019

Every year movie critics weigh in on what they consider to be the top 10 movies of the year. While the lists are not identical, the differences are usually in where a particular film ranks in the top 10 rather than whether or not it should be included. Here I am offering a much more specific list of what I consider to be the top 10 gambling movies–not for any particular year, but for all time.

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Keep in mind that this list is purely subjective. I have found other lists of top 10 gambling movies online, which I have looked at for comparison purposes, only to discover that each list is different. We all have our own personal preferences that not only reflect our different tastes in movies, but different interests and reactions when it comes to gambling and how we like to see it portrayed in films.

Furthermore, I have not even attempted to rank the films individually on relative merit from 10th place to first place. But I didn’t want to simply list them in any random order either. So, as explained below, I am organizing my top 10 gambling films into two broad categories. Then, within each category, I list and briefly describe the applicable films chronologically from the earliest release to the most recent.

Why movies about gambling are so popular

I know a few people who condemn gambling in any form and vehemently preach against it at every opportunity. But whether you love gambling, loathe it, or are basically neutral, it is never going to go away.

The activity, in one form or another, has been deeply ingrained in human nature since the beginning of time. Modern conveniences like the Internet and online and mobile gambling only make indulging in it easier.

So considering the enormous popularity of gambling, it is no surprise that it is prominently featured in many films, some of which you have undoubtedly seen.

I was asked to compile a list of the top 10 movies about gambling, which I am providing here. However, with so many worthy possibilities to choose from, if you disagree with any of my choices or think that one or more movies that are not on the list should be, I am not surprised. My own personal distaste for excessive violence and a barrage of strong language has meant excluding some films that others might have included, while other films that captured my fancy might not do the same for you.

I am not a professional film critic. Some of the films made the cut primarily because they are highly entertaining. Others relay an important message that every gambler needs to hear about the pitfalls of gambling when it becomes excessive and takes control over one’s life. The first category, which includes six films, is The Lure of Gambling. The second category, which includes four films, is The Dark Side of Gambling.

Six must-see gambling films that convey the lure of gambling

People gamble for a myriad of reasons. But regardless of whether it’s the fun and excitement, need or desire to win, pure greed, or some combination thereof that’s the prime driving force for a given individual, the lure of gambling is undeniable.

Realizing that NJ Gambling Websites readers comprise a very diverse group of gamblers, I chose six gambling films that I think will have mass appeal. All of them present the activity in a positive light. Whether your preferred form of gambling is on casino games, poker, sports, or horse racing, these films are enjoyable to watch.

But you’re more than just a spectator; you’re rooting for the characters you want to come out on top and maybe even identifying with them. Even the roguish characters have an admirable gutsiness about them that can be intriguing and captivating.

Presumably, one of the main reasons you gamble is for entertainment. So an entertaining film about gambling, like any of the following, wins an enthusiastic thumbs up from me.

The Cincinnati Kid (1965)

This film tells the story of a famous poker player back in the 1930s–well before your time. There’s a good chance you haven’t seen the film either since it’s more than a half-century old. But it’s just as relevant for anyone aspiring to be a better poker player today as it was to an earlier generation of players.

The late Steve McQueen starred in the movie as the up-and-coming young poker player Eric Stoner, aka “the Cincinnati Kid.” Stoner wants nothing more than a chance to play against and beat one of the best players of his time, Lane “The Man” Howard (played by Edward G. Robinson).

A friend arranges a private game, but another player who lost heavily to Howard previously has the cards fixed against him. The Cincinnati Kid objects because he wants the chance to beat Howard fair and square.

I won’t spoil the suspense as to what happens as the big game plays out. To find out, you will have to rent the movie and watch.

What makes this gambling movie relevant

As any poker tournament player learns the hard way, and this film is a good reminder, starting hands that look like that don’t have a chance sometimes win. Meanwhile, hands that look like “monsters” can turn into costly losses at the river to an even bigger hand. Sure it’s frustrating to have your Aces cracked when a player with 7-2 off-suit pairs both cards or when your full house loses to a bigger full house or a straight flush. But that’s poker.

The Sting (1973)

The 1973 movie The Sting is another one where gambling (poker and horse racing) are featured prominently. Yet there was no gambling at all when the people responsible for making this film picked Paul Newman and Robert Redford to play the starring roles. With a dynamic acting duo like that, how could the film not be a winner?

Then cast them as two con men, one a small-time grifter, Johnny Hector (played by Robert Redford) and the other the experienced pro, Henry Gondorff (played by Paul Newman) and make their mutual target a powerful crime boss.

After Hector had inadvertently made the crime boss a victim in a small street con and got caught, the boss had one of Hector’s friends killed. So Hector, eager to avenge his friend’s murder, enlists the help of Gondorff, who is a master con artist, along with a bunch of other con men who also despise the crime boss.

That’s all I am going to tell you about the plot. But trust me. You will need to pay close attention from start to finish. This action-packed movie manages to throw in so many exciting twists and turns, it’s a nail-biting thriller from start to finish!

What makes this gambling movie relevant

The Sting was nominated for 10 Oscars and won seven, including Best Picture, Best Director, and Best Original Screen Play. It was also selected for preservation in the US National Film Registry of the Library of Congress for being “culturally, historically, or aesthetically significant.”

Kenny Rogers in The Gambler and its four sequels (1980-1991)

Whenever the song or film title The Gambler is mentioned, one name immediately comes to mind: Kenny Rogers. Right now you are probably singing the words to the chorus of this familiar song to yourself. But on the off chance you have forgotten them, here they are:

“You’ve got to know when to hold ‘em,

Know when to fold ‘em,

Know when to walk away,

And know when to run.

You never count your money

When you’re sittin’ at the table.

There’ll be time enough for countin’

When the dealing’s done.”

No matter how many times you have heard Kenny Rogers sing this tune, it never gets old. So if you enjoy the song, but have yet to see the five made for TV gambling movies it inspired, by all means, do so.

Rogers plays high stakes gambler Brady Hawkes in all of the films. In the first film, he is traveling by train from El Paso to Yuma because his young son, who is being raised by his stepfather, needs his real father’s help. But much of the film is focused on his adventures on the way.

Of course, a gambler’s life is one adventure after another up until the day when he or she finally packs it in. So the saga continues.

Here is the 1980 film that got the ball rolling and, in chronological order, the four sequels:

1980: The Gambler

1983: The Gambler: The Adventure Continues 

1987: The Gambler, Part III: The Legend Continues

1991: The Gambler Returns: The Luck of the Draw

1994: The Gambler V: Playing for Keeps

What makes this gambling movie relevant

Unfortunately, for all of the Kenny Rogers fans out there who never got a chance to see him perform live, you won’t get that opportunity. Due to health problems, he had to cancel the last few concerts on his 2018 farewell tour, and he won’t be performing live ever again.

But you can see him for a lot less money by renting any or all five made for TV films in The Gambler series.

Rain Man (1988)

This classic movie will mesmerize you from start to finish. But it is especially enthralling for anyone who enjoys playing blackjack.

How blackjack differs from other casino games

An important difference between blackjack and most other casino games is that not just luck, but also skill, is a major determining factor in a player’s ability to win. More specifically, proper use of an advanced technique known as card counting can actually give some players a small edge over the house. This advantage does not guarantee winning, by any means, but does increase the likelihood of winning.

When the distribution of cards remaining to be dealt favors the house, the skilled card counter either won’t bet at all or only bet minimally. When the reverse is true, the skilled card counter will bet heavily.

Rain Man’s amazing card counting skills

Rain Man is a story about Raymond Babbitt, the autistic savant older brother of Charlie, a selfish car dealer. At the start of the film, Charlie (played by Tom Cruise) receives some unsettling news. He learns that his father from whom he was estranged, has died but bequeathed virtually all of his multimillion dollar estate to the institution where Raymond (played by Dustin Hoffman), a brother that he didn’t even know existed, lived.

Charlie wants an equal share of Raymond’s inheritance. But when his effort to get it fails, he moves on to Plan B. Raymond displays some of the typical symptoms of autism like rigid routines and lack of emotion. However, he also has a photographic memory and amazing counting skills, which Charlie gets wind of and decides to use to his own advantage.

Charlie is $80,000 in the hole for Lamborghinis for his customers that his creditors have seized because he failed to make the required down payments. So he takes Rain Man with him to Vegas to help him win the money at blackjack. Much to Charlie’s delight, Raymond takes to card counting like a duck to water. Eventually, the two brothers are thrown out of the casino, but not before they win $86,000, more than enough to cover Charlie’s debt.

Afterwards, Charlie decides to make up for lost time and have a good relationship with his brother. Raymond returns to the institution and Charlie promises to visit him.

What makes this gambling movie relevant

Rain Man was the recipient of four Academy Awards: Best Picture, Best Original Screenplay, Best Director, and Best Actor in a Leading Role awarded to Dustin Hoffman.

However, watching Raymond’s exploits in the casino is more entertaining than it is educational. The statistical advantage to be gained by counting cards as depicted in the film is greatly exaggerated and has no resemblance to reality. Moreover, today’s blackjack games employ “countermeasures” designed to further minimize that advantage. In most online blackjack games, the cards are reshuffled after every hand, making card counting, in effect, impossible. In Live Dealer Blackjack, the cut card is placed in the middle of an eight deck shoe, which makes card counting a waste of time since half of the cards are never dealt.

In Atlantic City, card counters can’t be barred like they can in Nevada casinos, but that doesn’t mean that they can bet whatever they please for as long as they please and expect to get away with it. A number of years ago, a very large and somewhat eccentric fellow whom the Atlantic City local card counters called Rain Man would stand behind a blackjack table and keep track of the cards. Then, when the count got high enough, he would raise a pencil high up in the air, and his partners would descend on the table like vultures to place $500 bets. They were lucky if they got to play one hand before the pit boss yelled “Shuffle!”

 Seabiscuit (2003)

All forms of gambling have their share of improbable upsets. But some of the most exciting and memorable are in the world of thoroughbred horse racing.

The 2003 film Seabiscuit, directed by Gary Ross and starring Tobey Maguire, Jeff Bridges, and Chris Cooper, was based on the best-selling novel by Laura Hillenbrand: Seabiscuit: An American Legend.

It’s surprising that a film about this spectacular racehorse was such a long time in the making since his racing career dates back to the 1930s, the end of the Depression Era. However, for readers of NJ Gambling Websites, here’s the good news. The next best thing to seeing the horse at the racetrack is now an option.

Seabiscuit’s heartwarming rags to riches story

The film tells the heartwarming true story of how three men, all down on their luck, meet and make it their joint mission to turn an equally unlikely prospect, a lightly regarded colt named Seabiscuit, into a champion racehorse. For Charles Howard, an automobile mechanic, life is especially tough, as he is trying to cope with both his only child’s death and the end of his first marriage. Howard, who is determined to find new meaning to his life, decides to enter the horse racing business. He buys Seabiscuit and finds a horse trainer and jockey who want to work with him, as they are not in a good place in their own lives either.

The problem is that the undersized, temperamental Seabiscuit, despite an excellent pedigree for racing, has a reputation for being “incorrigible.” But the new trio working with him, remain undeterred, see the horse’s potential, and are excited by the challenge.

Turning him into a winning racehorse is a long grueling process. But once Seabiscuit achieves success in minor races, Howard and his team have their sights set on bigger goals.

One of their dreams is for Seabiscuit to run against Triple Crown winner War Admiral. At first, War Admiral’s owner wants no part of it. But eventually, he gives in, and the highly publicized race occurs. More importantly, Seabiscuit’s amazing rags to riches story and improbable rise to fame captured the hearts of the whole country.

What makes this gambling movie relevant

Seabiscuit achieved his fame in the 1930s, when we weren’t around to see it. Yet anyone who has ever been down on his or her luck or is acquainted with someone who is can relate and cannot help but be inspired, whether a gambler or not. And for horse racing fans, getting to watch facsimiles of Seabiscuit’s races in the film and see how they play out is thrilling.

Meanwhile, the bettor in me couldn’t help but wonder what the odds were on Seabiscuit and how they must have shrunk as his fame skyrocketed. I would have also liked to see folks at the racetrack placing their bets.

But Seabiscuit is not a film about betting. It is a film about gambling because it shows how having a winning attitude and believing in yourself and your goals can make overcoming enormous odds possible.

21 (2008)

This is another film about card counting. 21 is based on the true story, as related in the best-selling book Bringing Down the House, about a group of students, mostly from MIT, who became a formidable blackjack team. Visiting Las Vegas on weekends over an extended period of time, the team won millions of dollars.

As pointed out in an article on, much of what is shown in the movie is pure fiction rather than an accurate portrayal of what really happened. For example, the romance between two team members and one player carelessly losing $200,000 in a single session, never occurred outside of the film.

Another type of incident portrayed in the film that never happened with the real team was team members being beaten up by casino security guards. This was Hollywood’s fabrication designed to make the visual effects more graphic and nothing more. This is not to say, however, that the casinos were not onto the MIT team and didn’t use other countermeasures against them. But strong-arm tactics like beating the bloody daylights out of a player is not something that today’s legitimate casinos do.

What makes this gambling movie relevant

Anyone with an appreciation for the game of blackjack, and especially those who have dabbled in card counting, will find this film, despite its many flaws, fascinating. The film shows that becoming a proficient blackjack player is a lot more difficult than one might think.

Moreover, the real MIT blackjack team was active in the early 1990s, and playing conditions have changed since then. Winning significant sums of money while remaining undetected for an extended period of time is much harder now.

The likelihood of an individual player today duplicating anything close to the success of the MIT team is extremely remote. See my relevant comments with regard to the film Rain Man because they also apply to this film.

Four must-see gambling movies about the dark side of gambling

People love to gamble, so it is only natural for Hollywood to focus on the glitz and glamour, often to the exclusion of gambling’s darker side. Here are four gambling movies that provide a chilling reminder of what can happen when gambling spirals out of control or the need to obey the law and do what is morally right pales compared to the lure of big money.

The Gambler (1974, 2014)

The original 1974 version stars James Caan, Paul Sorvino, and Lauren Hutton. Axel Freed (played by James Caan) is a Harvard-educated English literature professor with a gambling addiction.

Despite his gambling becoming more and more out of control, Axel somehow manages to keep it a complete secret from his family and girlfriend for a long time. But that changes when he loses $44,000 to his bookie. His mother bails him out, but instead of paying off the debt, he goes to Vegas, where he wins more money, only to lose it back again on more basketball bets.

When loan sharks come to his house in the middle of the night threatening to beat him if he doesn’t pay up, his girlfriend is disgusted. But this time, Axel’s family refuses to give him a dime, so he arranges with one of his college students, who happens to be the school’s star basketball player, to shave points on a game.

The plan works. But Alex’s insatiable need to tempt danger soon gets him into more trouble, and this time he gets seriously injured in a fight.

What makes this gambling movie relevant

Keep in mind that this movie was made back in 1974. Fortunately, both casino gambling and sports betting are now legal in New Jersey, and for the latter, all betting is up-front. You can only wager money that is in your wallet or in your NJ online gambling account.

So while it is still certainly possible for NJ bettors to bet a lot more than they can afford and even lose the rent money, at least they don’t face the added pressure of owing additional money to shady characters after the fact.

Even in 1974, when outside of Nevada, both sports betting and casino gambling were illegal, the portrayal of bookies and their bosses using strong-arm tactics to threaten or actually beat up non-paying customers is more Hollywood fiction than reality.

However, the film contains some memorable classic lines, to which any gambler can relate. One of Axel’s friends comments “Jeez, Axel, I have never seen such bad cards.” In another segment, Axel can’t understand how he could have lost so many basketball bets because when he checked the scores on the radio while the games were still in progress, his teams were winning. His bookie then asks him: “Where have you been? Siberia? Those where half-time scores!”

By the way, there is a 2014 remake of this film with Mark Wahlberg as Axel Freed, which I have not seen. I recommend that anyone who is currently gambling or considering it see at least one version of this film.

If you have a gambling problem, help is a phone call away

Legal gambling within one’s means, whether done solely for recreation or as a way to try to augment one’s income, is both exciting and fun. But when done to excess, it ceases to be either.

If you or anyone you know has a gambling problem, call 1-800-GAMBLER. Help is available 24-7.

Indecent Proposal (1993)

Financial worries can be the downfall of many couples, even those starting out in a healthy relationship. Indecent Proposal is a film about a married couple on the verge of losing their house. They are so desperate for money that they can’t think rationally. They make one reckless decision after another.

David (played by Woody Harrelson) is an architect, and his wife Diana (played by Demi Moore) is a successful real estate agent. The two of them were high school sweethearts who have been together ever since.

But when the recession hits them hard, instead of tightening their belts and trying to make their dwindling bank accounts last longer, they take their last $5,000 and head for Las Vegas. After a disastrous run at the craps tables, a billionaire they had never met before (played by Robert Redford) makes them a tempting offer–a million dollars in return for one night with Diana.

David and Diana accept the offer. The decision ultimately costs them their marriage.

What makes this gambling movie relevant

When people are desperate enough for money, they can succumb to all sorts of aberrant behavior they would not otherwise engage in, often with dire consequences.

Indecent Proposal received mixed reviews from the critics. However, it is worth seeing as a reminder that gambling is far from being a sure thing and definitely not a recommended way to deal with financial problems.

High Roller: The Stu Ungar Story

Winning the World Series of Poker (WSOP) Main Event even once is many aspiring poker players’ ultimate dream. However, the odds stacked against it are enormous. Stu Ungar and Johnny Moss were the only two poker players to date to win three WSOP Main Event tournaments.

The 2003 biopic entitled High Roller: The Stu Ungar Story depicts the fascinating but tragic story of a man who sought fame and fortune, achieved it, but couldn’t handle it, and ultimately lost everything.

Michael Imperioli plays the poker legend as the viewer gets an in depth look at this hard to believe but nevertheless true story. Stu Ungar’s whole life was a precarious roller coaster ride. But the rise from teenage card shark to world-class poker player was only one part of it. Another was his reckless racetrack gambling and chronic drug abuse.

Despite having won an estimated $30 million at poker, when Stu Ungar’s life abruptly ended in 1998 at age 45 in a cheap Las Vegas motel room, he had no assets to his name.

What makes this gambling movie relevant

The short, sad life of poker legend Stu Ungar is an extreme example of a man who was seemingly invincible at poker but anything but in his ability to manage other aspects of his life. Most of us will never become world-class poker players, much less win the WSOP Main Event. But what matters far more than any bracelet, or adoration of fans is the peace of mind that comes from leading a balanced life with a sense of purpose.

Molly’s Game (2017)

Molly’s Game is another film about gambling based on a true life story. The 2017 film starring Jessica Chastain, which I saw in Philadelphia, was based on Molly Bloom’s memoir with the same title.

What makes Molly’s story different from those in the other films I have described in this section on the dark side of gambling is that what got her into trouble was not her own gambling, but running illegal underground poker games.

Prior to her involvement with illegal gambling, Molly Bloom had career aspirations that were both lofty and legitimate. She was a world-class skier training for the Olympics, but a serious injury ended her skiing career permanently.

Then, instead of attending law school as planned, she moved to Los Angeles and got a job as a cocktail waitress. She then met a real estate developer who hired her initially as his office manager, but later to help run his underground poker games. Molly became so good at it, she started running her own game.

Move to New York

Problems developed with some of the players, though, so Molly moved to NYC to start a new underground game there, and once again, she was very successful.

But despite her clientele including some very wealthy players, among them members of the Russian and Italian Mafia, losing players who failed to pay up were a recurring problem. Molly then started taking out a piece of the large pots for herself, which was illegal.

Molly found herself in more trouble when she turned down the offer from the Italian Mafia to extort money from losing players. Afterwards she was attacked in her home at gunpoint and her mother’s life was threatened as well. Meanwhile, in an attempt to cope with all of the stress and aggravation, she became addicted to drugs. Then the FBI swooped in and seized her assets.

Two years later the FBI arrested her and charged her with running an illegal gambling operation with ties to the mob. Although she pleaded guilty, since this was her first offense, the judge sentenced her to community service, probation, and a $200,000 fine in lieu of prison.

What makes this gambling movie relevant

Since running high stakes underground poker games for personal profit is clearly against the law, it was only a matter of time before someone squealed and Molly Bloom was arrested.

Even though she was able to avoid jail time, the record of her criminal activity will affect her for the rest of her life.

Furthermore, long before her arrest, she was putting her life in danger with her use of illegal drugs and association with unscrupulous people.

For anyone tempted to get involved in the illegal gambling scene in any way, including patronizing these places as a customer, Molly’s Game will hopefully serve as a stern warning not to do it.

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