Tom Jolliffe puts his chips on ten essential gambling films…
The money goes down. You’ve placed your bets. Now it’s time for the nitty gritty. Win or lose. If you win, do you quit while you’re ahead or go again? Cinema has long held a fascination with gambling across its many forms, but the predominant focus comes back to the human element. It’s the (often hapless) gambler who has dug himself into a hole. Whether it’s cards, horses, sports games, bets or the spinning roulette wheel, there are an array of ways the unlucky gambler can lose his money. It tends to be that cinema brings us into the well trodden lifestyle of the gambler, already burdened with debt at the start and feeling as if their only way out is a winning hand/bet/game. Inevitably, there are complications and consequences, but this desperation often makes an engaging character and enthralling story. Here are ten essential films revolving around gambling.
Mississippi Grind
Ben Mendelsohn is the hapless middle aged gambler. Ryan Reynolds is the strange charismatic newbie to the circuit, oddly happy to lose money, who becomes something of a lucky charm. The two strike up an odd bond and a gambling road trip that meanders like a stray card in the wind. It’s compelling, with Reynolds exuding charm but as much restraint as we’ve seen from him, whilst Mendelsohn is superb. This captures an odd grimy romance of the circuits and the routine and there’s an interesting dynamic between the two leads.
Hard Eight
Paul Thomas Anderson’s first film is a fantastic neo-noir. Showing all the traits he’s since become known for, Anderson crafts a tale in an engagingly murky world with interesting character dynamics. Philip Baker Hall shines as an aging gambler who takes John C. Reilly under his wing. There are an array of great supporting actors among the cast too (Samuel L. Jackson, Philip Seymour Hoffman and Gwyneth Paltrow) and its an assured and gripping debut from Anderson, remaining one of his most lithe works.
Croupier
Mike Hodges (Get Carter) had a return to form with this underrated gem. Croupier carried a good reputation for a few years but has slowly disappeared (unfairly) into slightly forgotten territory. Clive Owen takes on a job as a croupier. He’s done it before, but the job (in South Africa) got to him eventually. His mantra has always been, ‘I don’t gamble.’ This aspiring writer gets reacquainted with this grim and sometimes frantic world. He’s fascinated by his colleagues and the punters but is particularly drawn to a beautiful South African gambler who is on a bad streak (Alex Kingston). She enthralls him enough to break a cardinal rule, not to engage with punters outside of work. All the while, his book in progress and its lead character begins to merge with him. He is Jack, the character is Jake, and soon Jake’s persona infects Jack’s. He’s lured into helping a heist and goes beyond his limits. To an extent the man who never gambles on the tables, has taken a different kind of gamble.
Uncut Gems
A down on his luck, hapless and compulsive gambler (Adam Sandler) has accrued large debts and just keeps on gambling. Collectors are hounding him and he’s awaiting a prized uncut gem that he’s sure will fetch a big price in auction. The Safdie brothers’ film pounds into life right away and doesn’t let up. It’s a relentless and gripping film, as Howard’s every decision seems to dig him ever deeper in a hole. There’s a crushing inevitability to the outcome, even after it seems Howard’s luck has finally come in. The tension builds almost to unbearable levels too. Meanwhile, Adam Sandler has never been better.
Bad Lieutenant
A morally bankrupt police officer on a path to self destruction, is riddled with gambling debts. He’s amoral, abuses his authority and succumbs to every hedonistic whim he can. He feels the walls closing in as yet another bet ends in loss, whilst the rape of a nun cuts even his moral center to the bone. He wants to find the perpetrators and he seeks a last act of redemption. Harvey Keitel’s performance leaves nothing behind. He’s sensational and enthralling, even as reprehensible and irredeemable as the character gets.
Lock, Stock and Two Smoking Barrels
Guy Ritchie’s dazzling debut probably remains his most re-watchable film. There’s a spark of brilliance throughout, even if it amalgamates some tried and trusted genre tropes (and is notably one of the post-Tarantino surge). The young cast are charismatic and engaging (including the four friends Nick Moran, Jason Statham, Jason Flemyng and Dexter Fletcher), whilst Vinnie Jones has a memorable cinematic debut. So many great lines, a deviously twisting plot and a killer soundtrack make Lock, Stock an essential piece of British cinema from the last 25 years.
The Hustler
Robert Rossen’s uber stylish and gripping film takes the gambling to the underground pool halls. A young, small time hustler (Paul Newman) lets ego get the better of him and challenges a local legend, Minnesota Fats (Jackie Gleason) to a high stakes match. He’s shown up and goes on a self destructive path. He gets back on the circuit but the grimy world leaves him at a moral quandary. Can he step away before he pays too great a price? The pool sequences are great, the cinematography is sensational and Newman and Gleason are superb. Newman would reprise his role in semi-sequel, The Color of Money. The Hustler, is superior but Scorsese’s follow on is still well worth a watch.
The Gambler
Something of an unsung classic from a golden period in American cinema, The Gambler saw James Caan, fresh from The Godfather, taking center stage. He’s a respectable teacher by day, hopeless gambler by night. Axel (Caan) is up to his eyeballs in debt but digs down instead of trying to find a sensible way out. This has similarities with Uncut Gems, with the feeling of unshakable destiny as Axel seems preordained to always make things worse for himself, even when he wins. Caan is fantastic in this gritty and stylish crime drama.
White Men Can’t Jump
Rival basketball hustlers team up to scam local circuits before setting their sights on more legitimate cash potential in a 2 on 2 tournament. The original Wesley (Snipes) and Woody (Harrelson) film. Woody is Billy Hoyle a likeable loser and constant bane of his girlfriends life. They’re on the run from mobsters because of Billy’s gambling debts, but he can’t shake off the addiction. Chance after chance and of course it becomes inevitable that Gloria (a superb Rosie Perez) will be pushed to her limit. Meanwhile Sidney (Snipes) is the assured hustler, but even he can’t account for the crushing realities of ghetto living he’s aspiring to escape from (his family home stripped of everything, including cash saved to get a new home). Full of great dialogue, fast paced basketball scenes and wonderful chemistry between Wes and Wood, White Men Can’t Jump is one of the best sport dramas of its era (from a master of the genre, Ron Shelton).
Wake in Fright
A rural Oz teacher, stuck in a dreary outback teaching post is off for the summer, and heading back to Sydney. He stops at ‘The Yabba’ on the way through, and therein begins a kind of anti-Alice in Wonderland, as he becomes ingratiated by the locals and falls foul of many of their customs (including heavy drinking and gambling). The Yabba folks hospitality counters their simple and sometimes raucous pursuits. He loses all his money betting, unable to get away. Increasingly, John (Gary Bond) begins to succumb to the world and the pursuits. He’s magnetised by it and repulsed at the same time, slowly horrified by the effect its had on himself. It’s a slow burning, atmospheric, sweaty and quirky odyssey in the Oz outback with a barnstorming Donald Pleasance.
See also, The Killing of a Chinese Bookie, Snatch, Casino Royale, Win it All, Oceans 11, and Rain Man. What’s your favourite gambling film? Let us know on our social channels @flickeringmyth.
Tom Jolliffe is an award winning screenwriter and passionate cinephile. He has a number of films out on DVD/VOD around the world and several releases due out in 2021/2022, including, Renegades (Lee Majors, Danny Trejo, Michael Pare, Tiny Lister, Nick Moran, Patsy Kensit, Ian Ogilvy and Billy Murray), Crackdown, When Darkness Falls and War of The Worlds: The Attack (Vincent Regan). Find more info at the best personal site you’ll ever see here.
Originally published August 4, 2021. Updated November 11, 2022.
