The Most Iconic Card Sharks in Modern Day Cinema

Aug 14

There are a lot of people who love gambling movies nearly as much as they love gambling. And really, what's not to like? You get the thrill of a high-stakes cards game from the comfort of a multiplex or even from your living room.

For a lot of people, these movies gave us a glimpse of Las Vegas casinos and card games. A lot of it was shaped by movies about Danny Ocean planning a high-stakes heist at all the top joints on the Strip or the Corleone family making a move on Moe Greene and the Tropigala.

But what movies about casinos and gambling really got it right? Here's a list of the most memorable, palm-sweating, risk-taking moments on the big screen and the card sharks that dared to pull it off.

1) Le Chiffre in Casino Royale

Not only did this movie bring back to fore the struggling 007 franchise but it also sparked the Texas Hold'em frenzy with its insanely high-stakes showdown between James Bond and Le Chiffre, the cold-hearted terrorist banker whose mathematical genius nearly toppled the indomitable Mr. Bond at the poker tables of Montenegro.

To be perfectly honest, in spite of his incredible poker talent, the guy has some fairly obvious tells: from a little temple twitch right up to weeping blood. All the same, he’s vicious as heck, crunches numbers like Deep Blue on speed and nearly single-handedly bankrupted MI6, so we reckon he’s earned a place on this list.

The final, incredible, ball-breaking hand brings four players all in, with successively impressive cards. But it's not exactly a shocker when it is finally revealed who come away as the top dog of this bunch — Bond. However, the testicular torture Bond endures hardly comes off as a worthy prize.

2) Steve McQueen in The Cincinnati Kid

This movie was a classic poker tale that featured a big-name ensemble bannered by Steve McQueen, the incomparable Edward G. Robinson, Ann-Margret at her trampiest and Jack Weston at his sweatiest. It also featured a catchy title ditty sung by the legendary Ray Charles.

A classic specimen of sharkish 60s suave, the character that McQueen plays —Eric “Kid” Stoner — is the poker prodigy whose strategic genius allows him to take his opponents to pieces with ease verging on contempt. Fearless in the face of more experienced rivals, the Kid is the kind of gambler to whom we all aspire: methodical, ruthless and so, so cool.

The proceedings don't really come to life until the final hand of five-card stud, which actually bears a lot in common with the Casino Royale showdown. It's a riveting sequence that only someone like McQueen could totally pull off. The final hand is a prolonged mano-a-mano with more tension than a Bernard Herrmann score and delivers an exciting punctuation mark to a movie that seemed to drag on for the first 90 minutes.

3) Paul Newman and Robert Redford in The Sting

This George Roy Hill-directed film that starred Hollywood royalty Robert Redford and Paul Newman was also a clever and well-researched exposition of elaborate race-track and stock-market swindles during that time. The movie was partly based on David Maurer's seminal work called “The Big Con,” which was an earnest study of the notorious scams run in the 1920s by con artists like Denver's own Lou Blonger and his Million Dollar Bunco Ring, The Sting is both a crowd-pleaser and an education in suckerdom, right down to the final standoff.

4) William H. Macy in The Cooler

Actor William H. Macy shines in one of his finest roles as the house jinx brought out to chill any player on a big run. He spends most of this under-the-radar indie from 2003 looking like a house falling down. He's a cooler, a loser hired by casinos to break other players' lucky streaks. That is until he falls in love with Maria Bello, who plays the role of a tough cocktail waitress who has more to her than meets the eye.

Macy actually becomes a walking lucky charm, losing the casino thousands, and infuriating his boss, a menacing Alec Baldwin in full-throated Glengarry mode who damn near steals the movie, with a cunning and calculated performance. “The Cooler” is a sexy, violent fantasy of disillusionment and crushed hopes, which if you think of it for a while, is very much like Las Vegas itself.

5) George Segal and Elliot Gould in the California Split

California Split is one of the more muted films directed by Robert Altman and it is a veritable tour of poker rooms, casinos, race tracks and other fields of doom. However, the real star of the show is the undeniable chemistry between the itching-to-bet George Segal and the stammering gambling neophyte Elliot Gould, which is nothing short of terrific. The aimlessness of their journey is the main plot point of this flick, to the extent the movie has one. When a man's obsessed with risk, winning doesn't satisfy, and even the hot streak of a lifetime doesn't guarantee a happy ending.

6. Clive Owen in Croupier

British actor Clive Owen plays the role of Jack Manfred, an aspiring writer and dashing bastard, who finds plenty of material to write about — such as corruption, lust and the kind of sangfroid that comes from watching people throw money away all night — when he takes a job at a London casino.

It’s funny, but there’s just something about this story of a struggling writer who gets sucked into the glamour of casino life that strikes a chord with audiences.

Anyway, Owen owns this role, oozing cool confidence as he juggles chips with superhuman dexterity while simultaneously carrying off an eloquent interior monologue.

In fact, Jack is exactly the kind of guy you want onside if you’re out to make a killing on the card table: efficient, reliable and meticulous Don't fret too much about the weird plot turns of the last act and enjoy Owen's sleek performance and the intelligent script, chock-filled with snappy dialogue and great noir narration.

7. Robert de Niro and Joe Pesci in Casino

“Casino” is based on the real-life rise and fall of Frank "Lefty" Rosenthal and Tony "The Ant" Spilotro, The movie is a signature Scorsese romp, with a lot of blood, Joe Pesci and Robert De Niro, kinetic camerawork, outrageous 1970s wardrobes, and a virtual cacophony of f-bombs.

De Niro plays the manager of the Tangiers, who slowly loses his fortune after getting mixed up with a common-street strumpet, Sharon Stone. In the meantime, he rhapsodizes about Vegas like a goombah philosopher. "The cardinal rule is to keep them playing and to keep them coming back;" "all the bright lights, and the comp trips, and all the champagne, and free hotel suites, and all the broads and all the booze. It's all been arranged just for us to get your money;" and the classic: "You can either have the money and the hammer or you can walk out of here."

Scorsese was so enamored with industry that the HBO show, Boardwalk Empire, tracks the rise of Atlantic City. Casino is also a movie that can be used to teach students about Vegas history and gambling as a business, which is something the characters end up ignoring while they're busy skimming the take, chasing the tail of Stone, putting someone's head in a vise or beating each other to death with baseball bats.

8. Matt Damon in Rounders

Unless you're Matt Damon, and you've been to the school of hard knocks and have already figured out that poker is all about brains, discipline, and humility, not bluster and luck. John Dahl's probe of the game is gritty and insightful, yet strangely hopeful. In more ways than one, it's a more meticulous and realistic treatment than you'll see in a lot of movies about gambling, despite the Hollywood touches.

Rounders is widely considered to be the Goodfellas of poker. Well, not in the greatest-Scorsese-movie-of-all-time kind of way but in the way that it made a lot of guys who resemble Ray Liotta believe that they could play the game just as well as Matt Damon did. Talk to any of the hotshot players at Magic City Casino's poker room, and unavoidably, they'll spew John Dahl's 1998 cult flick as gospel.

9) James Caan in The Gambler

James Caan's intense portrait of a gambling addict, who also happens to be college professor, lecturing on Dostoyevsky when he isn't hitting on 18 at the blackjack table or wheedling cash from his own mother, is inexorably somber. But it's also addictively watchable, following the professor's downward spiral to its logical conclusion.

Apparently, Caan was struggling with a cocaine habit during the filming of this neo-noir gem. A tough time for him no doubt, but it might explain the air of authenticity he brings to his performance as Axel Freed: a lifetime gambler in deep with the wrong people.

Axel stands as a cautionary tale to gamblers everywhere; he is a victim of the seedier side of our beloved pastime. Landed in more debt than the Lehman brothers and with the loan sharks circling, Axel’s disintegration is as painful as it is compelling.

10. Nick Moran in Lock, Stock, and Two Smoking Barrels.

The lead guy Eddy played by Nick Moran bets a fortune in a game of three-card brag only to lose it all to some improbable hand. Surely a dilemma all card sharks have faced at some point. Except, Eddy owes the dough to some mobster named Harry the Hatchet, and he has to pay it back at an amphetamine pace while being directed by a Guy Ritchie. The movie presents an endeavor that is no easy task. And while the realness meter of this particular movie is dubious at best, it remains an enjoyable and wild ride.

11) Warren Beatty as Bugsy

Bugsy Siegel, the Jewish gangster who founded Las Vegas receives the biopic treatment in this two-hour epic, which is widely known among movie lovers as the movie where Warren Beatty finally got Annette Bening. Siegel's idea to establish the first casino in the middle of the nowhere that was previously known as the Nevada desert was as irrational as a deadbeat poker player's belief that this next hand will finally be the one that wins back his welfare check.

12) Frank Sinatra in A Hole in the Head

We really can’t make a list of great gambling movie characters without mentioning the great Frank Sinatra, who all but personifies Vegas. In this Frank Capra classic, which was actually filmed at the Magic City Casino in 1959, Sinatra portrays a deadbeat dad with a penchant for losing money at the tracks. He ends the movie singing High Hopes, surely the unofficial theme song of desperate gamblers everywhere. Safe to say, this movie was a lot believable than Sammy Davis Jr. as a slick thief in the original Ocean's Eleven.

13) Nicolas Cage in Leaving Las Vegas

Nicolas Cage plays an adventurous archeologist with a gambling problem and a weakness for kind-hearted hookers. It all ends well as Cage went on to win an Academy Award.

Realness meter: (Spoiler!) In the end, the upstart loses to the man; that's as close to the bone as it gets folks.

14) Nick Nolte in The Good Thief

Nobody wants to see Matt Damon win a card game. We want to see a desperate, down-on-his-luck basket case win because, at the end of it all, that's what basically all gamblers are.

And if the basket case in the movie wins, then perhaps, we also win. In The Good Thief, that guy is Bob Montagne, a former thief and ace blackjack player saddled with a heroin addiction, and played by the patron saint of fuck-ups, Nick Nolte. Bob has a mantra and it goes like this: Play to the limit, no matter what the consequences. With its booze-filled, Leonard Cohen soundtrack, and neon-colored imagery, this movie is as close to poetry as the genre has ever produced.

15) Kevin Spacey in 21

Honestly, pretty much anything Kevin Spacey has a hand in virtually turns to gold, and crooked MIT Professor Micky Rosa is certainly no exception.

He’s a callous, amoral, greedy old professor who takes advantage of the genius of his star pupil Ben Campbell played by Jim Sturgess, whom he connives with to take on the blackjack tables in Vegas as a card counter. No sooner than Ben begins enjoying the fruits of his labor, Rosa tries to cheat him out of his winnings. He gets his just desserts in the end, but while his scam plays out, Spacey’s cocky self-assurance and utter lack of scruples are a filthy pleasure to behold.

That's the list. But before the howls of anger begin heading our way, here are a few honorable mentions that might get gamblers’ juices flowing:

  • Philip Seymour Hoffman's notable portrayal of a bank manager with a gambling habit in Owning Mahowny
  • The highly entertaining and suspenseful casino scene at the climax of Bob le Flambeur
  • The western comedy A Big Hand for the Little Lady
  • The Grifters, which was a slick descent into a small-time hustler predicament where the luck runs from bad to worse