You’ve Got To Know When To Hold ‘Em: Cinematic Gamblers

January 7, 2020
They might not be perfect, but these big screen gamblers are all utterly compelling.


Played with swaggering insouciance by Oscar winner Benicio Del Tor, inveterate gambler Franky “Four Fingers” (“Do you know why they call him Franky ‘Four Fingers’? Because he makes stupid bets with dangerous people, and when he doesn’t pay up, they give him the chop”) is the character that kicks off all the bloody, messy, and often hilarious shenanigans of Guy Ritchie’s epochal crime caper Snatch, heading from his native America to London with a diamond stolen in the midst of an Antwerp heist.


In this punchy, well made low budget indie from Half-Nelson and Captain Marvel co-directors Anna Boden and Ryan Fleck, Ben Mendelsohn and Ryan Reynolds are at the top of their respective games as the older, down-on-his-luck Gerry and the younger, flashier Curtis, who team up and then set off on a road trip through America’s Deep South, tipping a play to trawl through the region’s casinos with an eye to scraping back what they’ve let go in the past. Set in a world pre-dating 2020 pokies, Mississippi Grind is a telling trawl through America’s gambling dens.


An Oscars player back in 2003, The Cooler stars the inimitable William H. Macy (TV’s Shameless) as the much feared and indispensable Bernie Lootz, the so-called “cooler” of the title. A walking omen of bad luck, Bernie’s mythic status sees him employed by the top casinos in Las Vegas, who bring him in when a player is on a massive, house-breaking hot streak. But when he falls in love, the hapless Bernie finds that his power to cool a hot gambler has dissipated, and his big, bad, blustering boss (Alec Baldwin) isn’t happy about it.

BEN (21)

In this surprising 2008 gambling flick from Aussie director Robert Luketic (Legally Blonde) based on Ben Mezrich’s best-selling non-fiction tome Bringing Down The House, a pre-career-jettisoning controversy Kevin Spacey does his icy, hyper-intelligent act with aplomb, playing Mickey Rosa, a college maths professor who recruits his top students and then trains them to become house-breaking card counters. The film’s most compelling character, however, is Ben (Jim Sturgess), a gifted, working class Boston student who hooks up with Rosa to make some cash to pay for his college tuition. His moral dilemma gives the film admirable weight.


A master character actor of the first order, the late Philip Baker Hall (who gave a stunning, one-man-show tour de force in Robert Altman’s Secret Honor, playing US President Richard Nixon) gets his greatest role in this debut drama from Paul Thomas Anderson (Boogie Nights, There Will Be Blood), playing seasoned professional gambler Sydney, who takes John C. Reilly’s innocent John under his wing and shows him the ropes when it comes to the tricky night-time world of casinos, which are far different from any online casino.


Though you don’t have to deal with them if you’re trying your luck at Australian casino sites, or in most of today’s games of chance, the bookie used to hold much sway in the world of gambling. In Vincent Gallo’s brilliant 1998 debut Buffalo 66, the actor/writer/director plays ex-con Billy, who finds himself in deep with an intimidating bookie, played with menacing authority by the great Mickey Rourke.


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