10 Films That Show The Dark Side Of Gambling

Gambling may be a popular and fun pass time for many people around the world (everyone loves a little Swanky Bingo action, you know you do), but for some it can come with some major consequences – and the world of cinema has shown us this time and time again. This is 10 Films That Show The Dark Side Of Gambling.

10. Mississippi Grind (2015)

Ben Mendelsohn Mississippi Grind

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.

9. The Gambler (2014)

The Gambler Brie Larson

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.

8. 21 (2008)

Jim Sturgess 21

Director: Robert Luketic

Ben Campbell (Jim Sturgess) is a shy, brilliant M.I.T. student who – needing to pay school tuition – finds the answers in the cards. He is recruited to join a group of the school’s most gifted students that heads to Vegas every weekend armed with fake identities and the know-how to turn the odds at blackjack in their favor. With unorthodox math professor and stats genius Micky Rosa (Kevin Spacey) leading the way, they’ve cracked the code. By counting cards and employing an intricate system of signals, the team can beat the casinos big time. Seduced by the money, the Vegas lifestyle, and by his smart and sexy teammate, Jill Taylor (Kate Bosworth), Ben begins to push the limits. And soon enough, Ben becomes corrupted by greed…

Regardless whether there are a number of cliches and plot incongruities, this entertaining and fast-paced flick will find an audience hoping to learn how to beat the dealer. Based on the infamous math students of the MIT Blackjack Team, the film showcases the Las Vegas lifestyle and certainly defines the “what happens in Vegas” way.

7. Funny Games (1997/2007)

Funny Games Family

Director: Michael Haneke

It doesn’t matter which version of Funny Games you watch (although it’s proper to say the original was better), as they are essentially the exact same movie. Director Michael Haneke first made Funny Games in 1997 in Austria. 10 years later, he directed a shot-for-shot remake for American audiences. No matter which you watch, you can’t really win; Funny Games is going to disturb you no matter what.

In both films, a family of three is taken hostage in their summer home by two young men, who bet them they will be dead by 9 the next morning. The two captors toy with the family, and use a game of eeny-meeny-miny-moe to find out which of the family will die first. We won’t spoil it for you, but we’ll just say that there isn’t anything remotely funny about these games at all.

6. Bookies (2003)

Bookies Nick Stahl

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.

5. Owning Mahowny (2003)

Owning Mahowny 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.

4. Poolhall Junkies (2002)

Mars Callahan Poolhall Junkies

Director: Mars Callahan

Obsessed by the world of pool, Johnny (Mars Callahan) could be one of the best. But his mentor and “trainer” Joe (Chazz Palminteri), a shady hustler who decides how and who Johnny plays, is holding him back from his dream. When the day finally comes, Johnny breaks from Joe, which leads to only one thing — violence. Joe is beaten up by some of Johnny’s buddies as a sign to leave him alone, and with this final act of freedom, Johnny leaves the world of pool-sharking.

After an ultimatum from his girlfriend Tara (Alison Eastwood), Johnny finally commits to a “real” job in the construction business, but is soon miserable there. He finds himself spending most of his time with his younger brother Danny (Michael Rosenbaum) who it seems is following in his footsteps on the road to a life Johnny left when he broke from Joe. As for Joe, he is bent on revenge for the beating he took, and soon he has a new protégé Brad (Rick Schroder) who is just as good if not better then Johnny. And he’s got his eye on Johnny’s brother.

3. Cruel Intentions (1999)

Cruel Intentions Bet Scene

Director: Roger Kumble

Kathryn Merteuil (Sarah Michelle Gellar) and step-brother Sebastian Valmont (Ryan Phillippe) are a deliciously entertaining villain pairing in this wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a diabolical wager of sexual conquest without consequences. The pawns? The naive Cecile Caldwell (Selma Blair) and the virginal Annette Hargrove (Reese Witherspoon).

It’s summer break, and Kathryn has been dumped by her beau for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Cecile by deflowering her and turning her into a tramp – thus humiliating her ex by delivering Cecile to him as damaged goods. After reluctantly agreeing, Sebastian sets his sights on a greater challenge – the new headmaster’s daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries. Sebastian bets Kathryn that he can seduce the pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled biblical, something he’s wanted since he’s their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat. Of course, none of this turns out good for anyone in the end.

2. Hard Eight (1996)

Hard Eight Samuel L Jackson

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.

1. Casino (1995)

Sam Casino

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. 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.

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