10 Enthralling Movies About Gambling

It’s not exactly a secret that the internet has now become a large part of the lives of millions of people all over the world. One of the ways in which this unique medium has influenced us is in regards to online gambling. As soon as the technology became available, a number of casino operators raced to the forefront, bringing us online casinos, sports books, and even poker sites.

Look at a company like Ladbrokes (get your £50 Ladbrokes free bet if you haven’t already), which recently hired the CMO from their competitor William Hill. They’re bending over backwards to push the gambling landscape forward.

But what about before the online gambling revolution? Well, over the years, Hollywood has given us views of gambling from every side imaginable; the good, the bad, and the not so pretty. So please join us, if you will, as we take a look at 10 diverse films about gambling in all its glory.

10. The Cincinnati Kid (1965)

Cincinnati Kid Scene

Director: Norman Jewison

The Cincinnati Kid follows Eric Stoner (Steve McQueen); known mostly as “The Kid”, as he tries to become “The Man”, otherwise known as the best stud poker player around.

The film is set in depression-era New Orleans in the smoky backrooms and pool halls where the professional gamblers go to work. The beginning scenes show examples of the danger that is often associated with high-stakes gambling as The Kid fights off thugs that he wins money from.

Director Norman Jewison’s tight pacing moves the narrative along briskly, keeping the gambling scenes tense all the way through. His use of subtle lighting and frugal, but on-point sound and music queues provide for a constant feeling of uneasiness. This gives way to a climactic poker hand that will have any audience sitting forward in their chairs.

9. A Big Hand For The Little Lady (1966)

Little Lady Movie

Director: Fielder Cook

A naive couple and a child arrive in town on the way to San Antonio, Texas to buy a farm there. There is a poker game between the richest men in the region. The man (Henry Fonda) cannot resist it and though he is a terrible poker player, enters the game betting all the money of his family.

In the climax of the game he suffers a heart attack. His wife (Joanne Woodward) then takes his place at the table. That’s the only way of recovering their savings. But there is a little problem. Can anybody explain her how to play poker?

Just like in a poker game itself, A Big Hand For The Little Lady lets it all ride until the final action, with a “kicker” you truly won’t see coming. We won’t ruin it for you here, but in a movie where the odds are seemingly stacked, the real action may have nothing to do with the cards. A film that’s relatively unknown to most poker players, A Big Hand For The Little Lady deserves a watch. It’s a film that proves that sometimes the best way to learn a lesson is by sitting down at a poker table.

8. Let It Ride (1989)

Jennifer Tilly Let It Ride

Director: Joe Pytka

Jay Trotter (Richard Dreyfuss) is going through a rough spot with his estranged wife Pam (Teri Garr) and feels like he’s making very little progress. He feels his luck change when his cab driver friend Looney (David Johansen) plays him a tape he made of people talking in the back of his taxi. One of the conversations is between two people that claim they’ve fixed an upcoming horse race. Jay decides to take the information seriously, and heads to the track immediately.

As he meets up with all the gambling-addict regulars he considers friends, he decides to bet on the fixed horse; a longshot at best. When he wins, though, his day begins to take on an almost epic quality. Could he indeed become rich by simply hanging around the track all day and betting on horses? Or will it just ruin his marriage even further? He soon discovers that, out of the weirdest circumstances, come the most unusual friends and supporters, and his day becomes very interesting.

Only in the movies can you come across selfish bastards that you actually like. Of course it helps when your bastard is played by the likes of Richard Dreyfuss. Bonus points for the appearance of a young (and ridiculously sexy) Jennifer Tilly.

7. Bookies (2003)

Nick Stahl Bookies

Director: Mark Illsley

After losing a wad of cash gambling, college friends Toby (Nick Stahl), Casey (Lukas Haas) and Jude (Johnny Galecki) get smart and realize they need to be the bookies, not the gamblers. Before long they’ve got a thriving business that earns them the unwelcome attention of some local mobsters.

In a movie with this storyline, one might expect a certain element of predictability. But surprisingly one great thing about this movie is you are kept wondering where it is going. You’re never sure how it’s going to end or what will happen to the characters as it plays out. This unpredictability, along with the element of realism regarding many of the procedures in the real betting world, is one of the best aspects of the film.

This is one of those undemanding pieces of entertainment that somehow creep up on you and force you to enjoy them. This one’s doubly recommended to those familiar with the joys and sorrows affiliated with sports betting.

6. Croupier (1998)

Clive Owen Croupier

Director: Mike Hodges

Jack Manfred (Clive Owen) is an aspiring writer going nowhere fast. He soon realizes that his current life as a casino croupier has all the ingredients of a great novel.

Croupier is a wonderfully written portrait of the gambling world from the perspective of someone on the other side of the felt. It’s an insightful analysis of the psychological turmoil of a gambler’s mind. Our main character’s voice provides intermittent background narration to the action on screen and details how he becomes split between the blond headed Jack, the author, and the black haired Jake, the amoral croupier. The two divergent personalities battle for control of Manfred, most markedly in his desire to gamble. Jack refuses to gamble, but Jake finds himself slipping into more serious wagers that involve his personal safety and perhaps even his life.

In one complex narrative, his mind works like an automated abacus as he adds and subtracts variables and calculates his chance of survival. Manfred ultimately concludes the popular opinion of gamblers, that they subconsciously yearn for their own destruction, is incorrect. Instead, he surmises that gamblers wish the obliteration of everyone else in the world and relishes his ideal position as a professional server of self-destruction.

5. Mississippi Grind (2015)

Mississippi Grind Scene

Directors: Anna Boden, Ryan Fleck

Compulsive gambling, and likely any other form of addiction, depends on either a heavy dose of delusion, the reckless hopefulness that despite the odds you’ll still come out on top, or a masochistic drive toward self-sabotage. Or else it’s a large helping of both. Mississippi Grind focuses on two individuals who share these characteristics in spades.

Down on his luck and facing financial hardship, Gerry (Ben Mendelsohn) teams up with a younger charismatic poker player named Curtis (Ryan Reynolds) in an attempt to change his luck. The two set off on a road trip through the South with visions of winning back what has been lost.

Attention must be called to some really great moments as tension builds between the pair’s differences. Most notably is a scene where they exchange each other’s weaknesses in letting on their gambling tendencies, while applying it to a general personality. One such example is Gerry slumping into his seat not just when he has a bad hand, but feels a drop in confidence as a human being. It’s simply really smart writing and a great way to integrate the topicality of the movie into dialogue. Quite brilliant indeed.

4. Owning Mahowny (2003)

Philip Seymour Hoffman Owning Mahowny

Director: Richard Kwietniowski

The fact-based Owning Mahowny follows Dan Mahowny (the late Philip Seymour Hoffman), the youngest assistant manager at one of Canada’s largest banks. A figure of few words and fewer distinguishing character traits, he’s the classic man in the gray flannel suit – or he would be, if gray flannel fit into his budget. Taking frugality to its extreme, the character dresses in cheap clothes, carries a tattered briefcase, and drives an exhaust-spewing car at least 10 years past its prime. Why spend money on such niceties, after all, when doing so would only cut into his gambling funds?

As the film opens in 1980, flashy bookie Frank Perlin (Maury Chaykin) happily relieves our main character of most of his money. But when the money starts to run out, Mahowny begins resorting to desperate measures to keep afloat, skimming from other people’s withdrawals and creating fictitious clients with deep wells of credit.

Owning Mahowny is an unflashy but fascinating meditation on addiction and greed. It’s a movie that rejects the pyrotechnics, glamour and spectacle-mongering of mainstream Hollywood yet manages to engage, connect and transfix to an extraordinary degree.

3. Rounders (1998)

Rounders Matt Damon

Director: John Dahl

Mike McDermott (Matt Damon) is a law-student with card playing aspirations. He wants to become a rounder, a professional player at the Mirage, in Las Vegas. Mike ends up betting his entire bankroll in a game against local mobster Teddy KGB (John Malkovich) and witnesses his dreams going down the toilet on a single playing hand. He swears off cards and starts doing grunt work for a fellow rounder named Joey Kanish (John Turturro).

It’s not before Mike’s old friend Worm (Edward Norton) gets out of prison and in trouble again that he gets the urge of playing cards once more. It’s both nature and necessity calling Mike, but it might very well cost him everything he has.

Rounders single-handedly motivated millions (maybe not millions, but a lot) of people to play poker competitively. The movie was very under-appreciated at the time it was released namely because it was ahead of its time. It was only later that it was recognized as being a precursor to the explosion in the popularity of poker. And although Rounders remained mostly unnoticed by the masses, it attained the ultimate cult status in the poker world. It’s rare to play in a poker game with friends and go through the whole night without someone quoting at least one line from the movie.

2. Casino Royale (2006)

Casino Royale Gambling Scene

Director: Martin Campbell

The 21st film in the James Bond Series, Casino Royale was the first to star Daniel Crag in the lead role. After earning his double-0 status, Bond is sent on his first mission to investigate the dealings of a banker named Le Chiffre (Mads Mikkelsen) who has been using his clients’ money to short-sell stock in successful companies before engineering terrorist attacks to profiteer from the sink in share prices.

After Bond stops an attack in Miami at the unveiling of a new airliner, Le Chiffre is forced to find a way to recoup his losses by setting up a high stakes card tournament at the Casino Royale in Montenegro. With the assistance of treasury agent Vesper Lynd (Eva Green), Bond enters the tournament in an attempt to stop Le Chiffre from winning his money back and in turn closing down his operation altogether.

Casino Royale resurrected the Bond franchise and took it in a more action-packed direction with the brawn of Craig a far cry from the smoothness of Connery, or charm of Brosnan. Instead he became a cold, ruthless killer, and that’s just on the poker table.

1. Casino (1995)

Casino Final Scene

Director: Martin Scorsese

In much the same way as Goodfellas before it, Casino is another collaboration between crime reporter Nicholas Pileggi and Martin Scorsese, and one that also details the life of a career criminal: Frank Rosenthal (renamed as Sam “Ace” Rothstein in the film). Unlike Scorsese’s earlier gangster film though, Casino was a much more glamorous and indulgent affair, detailing the life of Rosenthal (Robert De Niro) as he rose up to a position of prominence as the manager of a mob-run Las Vegas casino.

Nicky Santoro (Joe Pesci) was Ace’s extremely violent sidekick on their way up in the shadow of the criminal world, and Ace isn’t exactly thrilled when Nicky also relocates to Vegas. Ace meets and marries professional hustler Ginger McKenna (Sharon Stone), a gorgeous but money-hungry gold digger with an unhealthy attachment to small time hustler Lester Diamond (James Woods). Eventually Ace’s life begins to unravel: he insults the wrong local power brokers and runs afoul of Vegas’ licensing requirements; Nicky’s violent methods reflect badly on Ace’s business; and Ginger looks to rob him blind and make off with their daughter.

Visually, Casino is quite stunning and manages to really capture the excitement and glitz of gambling in a casino. So long as Casino stays focused on the excesses – of language, of violence, of ambition – in the life-styles of the rich and infamous, it remains a truly smart and knowing spectacle. And the ultimate cautionary tale.

Any other films you’d like to add to the list? Let us know in the comment section below.

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