Mr Lucky (1943)
No contemporary rom-com would ever make this list but what we have here is Cary Grant portraying a shady gambler who tries to scam a war relief charity by taking the identity of a dead gangster only to have a change of heart after falling for a wealthy socialite. Black and white, exuding 1940s Hollywood glamour, complete with all the black spots flickering and sound crackling, this old-timer exploits the “bad guy gone good” theme in a non-obtrusive elegant manner. So, Nicholas Sparks, you can use that Notebook of yours to jot some notes on a good romance. Just imagine what the Blood Bank scene would have looked like had Hitchcock directed it.
The Cooler (2003)
Bad luck incarnate Bernie Lootz, portrayed by William H. Macy, is a professional loser who has found a way to capitalise on his uncanny ability to lose every single bet he makes. Paying off a debt to casino manager Shelly Kaplow (Alec Baldwin), Bernie is a full-time “cooler” responsible for restoring the house edge by ending high-roller streaks as he seems to be able to transfer his bad luck onto other players. Bernie’s fling with a waitress somehow seems to weaken his cooling powers causing him and his boss a big deal of trouble. With great performances and a fun premise, the film accentuates the whimsies of fate and the idea of superstition and luck in gambling.
Fear and Loathing in Las Vegas (1998)
Before his streak of colourful quirky characters, Johnny Depp did an outstanding performance as Raoul Duke who takes a ride to Las Vegas in search of the American dream together with a psychotic lawyer. This adaptation of Hunter S. Thompson’s novel of the same name follows their psychedelic journey, infused with a lot of and different kinds of drugs and alcohol. The duo fall short of reaching their American dream goal, crossing paths with disillusioned hitch-hikers, gamblers, and of course the odd police officer in a run of surreal experiences, as the intoxicating substances gradually take hold.
Owning Mahowny (2003)
Philip Seymour Hoffman plays Dan Mahowny – a Toronto bank manager who seems like a capable helpful professional in a gray suit, invested in his career and focused on frugality. A scratch beneath the surface reveals that the quiet and mild-mannered man is actually stealing money from his clients’ bank accounts in order to fund his gambling addiction. Hoffman does a brilliant performance as he portrays exactly what gambling addiction does to players – it’s not the thrill of the wins or the despondency of the loss – it’s the entire process of losing control.
Hard Eight (1996)
This neo-noir thriller is Paul Thomas Anderson’s debut with an original storyline and compelling characters. Philip Baker Hall plays a gambler past his prime who becomes the unlikely father-figure for a young kid (John C. Reilly) down on his luck, in love with a waitress, and short of money he needs for his mother’s funeral. Although it lacks the dynamics of other gambling movies, Hard Eight places the emphasis on the human story and character depth. A soft, sort of a languid story, the movie goes into the details of gambling schemes, but never loses the focus on the mistakes, experience, and relationship of the characters.
With so many gambling movies focusing on the players’ stories, Croupier is a rare elegant gem that tells the story of the dealer as the link between his bosses and the customers. Clive Owen does a stunning performance as Jack Manfred – a struggling writer working as a croupier who narrates his own story in the third person. Detached and emotionally cold, Manfred seems convinced of his capability to stay in control of his life, narrate it, and write it into a novel. He doesn’t gamble at the casino but seems to be placing high bets in his personal life, as he finds himself entangled in a casino heist and juggling three women.
Okay, what do we have here – John Malkovich portraying a mental Russian mobster and a Will Hunting with a twist facing off in a no-limit, heads-up game of Texas Hold’em. Does it get any better? This movie explores the grim side of addiction in a nonchalant way. Brilliant performances by both Malkovich and Matt Damon show there’s nothing glamorous about queasy fascination with danger and the short-lived adrenaline rushes brought on by the fear and thrill in gambling. The dark humour in this neo-noir, however, prevents you from contemplating the meaninglessness of life and imperfect human nature as you can’t be getting all philosophical while watching a gangster munching on biscuits, can you?
The Cincinnati Kid (1965)
It’s been over 50 years since the premiere of one of the most iconic gambling movies ever and the debate over the scene with the last hand still instigates vehement debates among gamblers to this day. Poker experts are more concerned with how implausible and even “laughable” it is, throwing poker out the window, while movie critics tend to focus on the motive of growing up and coming of age and the metaphor of experience versus the imperious spirit of youth. Whether you’re interested in the mechanics of stud poker and you’re exploring all opportunities you might find yourself facing, or you’re just a sucker for the good old Hollywood classics, bump this up in your watching list.
The Gambler (1974)
The Gambler offers a glimpse inside the mind of an addict in a way that no other gambling movie really does. Carried by brilliant performances, the film explores the gloomy world of gambling addiction from the momentary jittery panic of losing a game to its further development into a consuming need for deeper and darker obsessions. James Kaan builds up a genuine and authentic character unlike any we’ve seen so far – Axel Freed, a troubled college teacher who has a fascination with danger and not only invites it to his life but even seeks and woos it, going further down the path of debt and self-destruction; a sobering reminder of the precarious nature of compulsive gambling.Casino (1995)
Based on a real story brought to the screen with the mastery of Scorsese and the stunning performances of Robert De Niro, Joe Pesci, and Sharon Stone, Casino is probably the hands-down ultimate gambling-related movie classic that tops any list. The film makes us feel like we’re having the curtain lifted from a scene that we really should avert our eyes from for our own safety. De Niro portrays a bookie who has to run Vegas casinos for his mob bosses, while Joe Pesci’s character Nicky Santoro is a thief and a killer whose recklessly violent behavior puts them both in danger. In a true Scorsese dynamic editing, Casino stands out from the director’s other mob movies with some of the most memorable scenes in the history of cinema, taking gambling on a macro level – behind closed doors where the steaks are really, really high.