10 Diverse Films About Gambling

Ace Casino
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. And 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 new bingo sites.

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 Big Town (1987)

The Big Town Matt Dillon

Directors: Harold Becker, Ben Bolt

In this drama set in 1957 Chicago, J.C. Cullen (Matt Dillon) is a small-town gambler who heads to the Windy City to hit it big. Far from making the fortune he set out to find, he instead becomes the pawn of two high rollers (Lee Grant and Bruce Dern), gets caught in a love triangle with Lorry Dane (Diane Lane) and her strip-club owner husband (Tommy Lee Jones) and becomes involved with another woman, Aggie Donaldson (Suzy Amis), to boot.

Despite its narrative shortcomings, The Big Town offers many cinematic pleasures: the pacing is particularly snappy, juggling multiple subplots with ease, a fantastic soundtrack and remarkable set design. The sets in question evoke a 1950s Chicago complete with neon signs, bold marquees, and warm diner lights awash in bursts of primary color that bring to mind the world of Warren Beatty’s Dick Tracy (which would arrive in theaters a few years later). Though not as evocative of comic book panels as Dick Tracy, the film’s nostalgic design creates a world that’s absolutely brimming with life. Definitely worth a look.

9. Let It Ride (1989)

Richard Dreyfuss 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.

8. God Of Gamblers (1989)

Chow Yun-fat God Of Gamblers

Director: Wong Jing

Watch any five-minute selection of God Of Gamblers, and you might not know what sort of film you’re watching. Watch the whole movie, and you still might not know. For a time the highest-grossing film in Hong Kong history, God Of Gamblers is, from scene to scene, a broad farce, a gangland action film, a slick drama set in the glamorous world of high-stakes gambling, a revenge thriller, and a slapstick comedy.

Do San (Chow Yun-Fat) is a slick professional gambler on a seemingly endless winning streak. On his way to defeat a rival in a card game, Do’s streak comes to a close when a head injury leaves him brain-damaged. Reduced to the mental capacity of a child, his friend “Knife” (Andy Lau) and Knife’s girlfriend Jane (Joey Wong) are left to care for him. They soon realize that his gambling abilities have been left intact, and in a series of events reminiscent of Rain Man, Do makes a comeback.

Great stuff here, where else are you gonna see Chow Yun-Fat act like a child and a badass gambler in the same movie?

7. Casino (1995)

Casino Tables

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.

6. Hard Eight (1996)

John C Reilly Hard Eight

Director: Paul Thomas Anderson

For reasons that will not become clear until much later, an aging gambler (Philip Baker Hall) takes a down-on-his-luck man (John C. Reilly) under his wing and begins to teach him the tricks of the profession in this dark drama set in the world of second-tier casinos and anonymous hotel rooms.

The two form an exclusive, almost paternal partnership, disrupted only by the arrival of a cocktail waitress (Gwyneth Paltrow) and a bullying con man (Samuel Jackson, in a role that may have stumbled upon the very definition of evil). Though on the surface, this is a classic film-noir set-up, Paul Thomas Anderson’s script and deliberately paced direction take a detour into much deeper emotional territory – and the superior performances of all involved respond in turn.

In actuality, this film is little more than a small resonant mood piece whose hard-bitten characters are difficult to like. But within its self-imposed limitations, it accomplishes most of what it sets out to do… and it does so exceptionally well.

5. Croupier (1998)

Croupier Movie

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.

4. The Cooler (2003)

The Cooler Dice Tattoo

Director: Wayne Kramer

Bernie Lootz (William H. Macy) is a loser of epic proportions. Just his bad luck alone is enough to turn the luck of anyone who comes near him. Losing is even his profession. Lootz is a cooler at an old school Vegas casino called The Shangri-La. His boss is Shelly Kaplow (Alec Baldwin), who is a firm believer in doing things the way of old Vegas.

Much to Shelly’s dismay, Lootz’s luck takes a sudden upturn when he meets his personal lady luck in the form of a beautiful cocktail waitress named Natalie Belisario (Maria Bello). She sees Bernie for what he is: an honest, nice guy. Now Bernie’s got a girl and luck is on his side. When Shelly sends him to “cool” a table, it doesn’t work and the patron continues winning. Naturally, things go left from there.

As a character study of a weary man who has had it with the scuzzy lifestyle of living in Vegas and yearns to get out, only for mounting road blocks to keep getting in his way, The Cooler is low-key and quite perceptive. It’s a small complex movie that packs a big punch.

3. Owning Mahowny (2003)

Philip Seymour Hoffman Gambling Movie

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.

2. Rounders (1998)

Matt Damon Rounders

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 frankly because it was quite 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.

1. The Gambler (2014)

The Gambler Mark Wahlberg

Director: Rupert Wyatt

“I’m not a gambler,” insists Jim Bennett (Mark Wahlberg), the title character of The Gambler, though both his actions and the name of the film chronicling them beg to differ. English professor by day, wannabe high roller by night, and shiftless, washed-up novelist by both, Jim makes his first appearance at a shady Los Angeles gambling den. Here, in the film’s opening scene, he wins big at the blackjack table, doubles down and loses it all, wins again on money staked to him by a loan shark, and then blows all of that on another foolish bet—all within 10 minutes of running time, and without a second of hesitation.

None of this looks like the type of behavior one might expect from a man who doesn’t have a problem. Yet as Jim gets deeper and deeper into trouble, and the details of his charmed life shift into focus, an alternate explanation for such reckless wagering presents itself. Maybe Jim isn’t a gambler. Maybe he’s just a rich asshole with a death wish.

Based on the 1974 film of the same name, here, The Gambler is refashioned into a swaggering California crime comedy about a golden boy rebelling against his own privilege, mostly by flushing every dollar he can get his hands on down the toilet.

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

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