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Ten Luminous Liars: My Favorite Cinematic Crooks and Con Artists

31 March 2010 Stories and Appreciations 65,922 views 3 CommentsPrint This Post Print This Post Email This Post Email This Post

My movie heroes have always been crooks. Confidence men and thieves are abundant in the real world, and nearly of them are despicable human beings … but in movies, these crooks display an ability I often wish I had: The ability to talk their way into anything, from a safe full of money to an escape from confinement, using nothing more than their gift as storytellers. Explosives and kung-fu won’t do you any good if a good confidence artist reached the objective before you did, and told his convincing tale.

Here are ten of my favorite crooks and liars from Hollywood films. These are my superheroes — stronger than Batman and Godzilla rolled together. Any one of these characters could take on Batzilla and get away with his wallet and hubcaps.

Henry Gondorff of “The Sting,” played by Paul Newman. I don’t think anyone has played a confidence man with more of that namesake ingredient than Paul Newman poured into playing Henry Gondorff. Gondorff keeps us guessing from the beginning, when we meet him as a washed-up drunk, to the film’s closing minutes, when he shoots a friend in the back. Gondorff’s most prominent feature, those piercing blue eyes of Newman’s, do much of his work for him: They pry the truth out of his reckless, evasive young partner Johnny Hooker (Robert Redford), and they glint with shameless malice when Gondorff puts the screws to crooked businessman Doyle Lonnegan (Robert Shaw). And Gondorff gets to utter one of my favorite greetings in film: “Pleasure to meet ya, kid; you’re a real horse’s ass.”

Jack Foley of “Out of Sight,” played by George Clooney. Or “pretty much every other part George Clooney has played.” There’s something about Clooney’s smooth, glib movie-star persona that naturally lends itself to confidence work, and a good number of the characters he’s played — including, but not limited to, Danny Ocean, Michael Clayton, and Mr. Fox — have been built on the skeletons of confidence men. None of them have had the swagger of the Elmore Leonard-written Foley, though. Within the first five minutes of “Out of Sight,” Foley manages to rob a bank with little more than a slight grin, a good head of hair and bunch of friendly prevarications. He’s not carrying a gun, or even wearing a tie.

Simon Dermott of “How to Steal a Million,” played by Peter O’Toole. Even the title of this 1966 film is a con: O’Toole’s Dermott and Audrey Hepburn’s Nicole Bonnet don’t steal a million dollars, or a million pounds, or a million of anything. They boost a forged sculpture which only has value to the daughter of the man who forged it, and to the clueless patsy who bought it; I don’t want to give too much more away. Suffice it to say that the only thing that Dermott really steals is the affections of young Nicole, which O’Toole handily does in his usual ways: with the soft-spoken elegance and impish smile that’s felled everyone from Katharine Hepburn to the Ottoman Empire. The long con Dermott plays has nothing to do with the one Bonnet thinks he’s playing.

Verbal Kint of “The Usual Suspects,” played by Kevin Spacey. Unlike Simon Dermott, Verbal Kint is not much to look at — he has a palsied hand and foot, a permanent hangdog expression and a cheap haircut. But that’s all part of the con, you see: Kint uses these liabilities to get people to misjudge him and to dismiss him out of hand. That allows Kint to tell tales like the one he tells to driven, inquisitive customs agent Dave Kujan (Chazz Palminteri)– the best tale that’s ever been told, a tale that reshapes reality around it. As Kint leaves the picture, you suddenly realize that that even though you’ve heard him talk nonstop for the better part of two hours, you don’t know a thing about him. That’s a real confidence man at work.

Harry Powell of “Night of the Hunter,” played by Robert Mitchum. Have I ever told you the story of left-hand, right-hand? The murderous phony “minister” Harry Powell, played with great relish by Robert Mitchum, has “love” and “hate” tattooed on his knuckles, and while he’s quick to show you the “love” hand, that’s only so you won’t see the Hate Express rollin’ in. A handsome and effortless charmer, Powell seduces recently-widowed women with his piety and rich, buttery voice, then takes their money and kills them — but he doesn’t believe himself a demon; he actually thinks he’s doing God’s work. He’s conning only himself. Someone with a delusion this deep can only be taken down by an elderly woman and a pair of meddling kids.

Jimmy Dell of “The Spanish Prisoner,” played by Steve Martin. “Good people, bad people, they generally look like what they are,” says “problem solver with a heart of gold” Jimmy Dell. David Mamet, the playwright and director who made “The Spanish Prisoner” and a host of other great con-artist classics (including “House of Games,” “American Buffalo” and “Heist”), took that line to heart in casting Steve Martin as Dell; the comedian and actor can look like both good and bad people, depending on how the light catches him. Martin is never anything less than likable, even as he ensnares hapless businessman Joe Ross (Campbell Scott) in a more-or-less inescapably fatal web of deceit.

Jackie Brown of “Jackie Brown,” played by Pam Grier. Quentin Tarantino adapted Elmore Leonard’s 1992 novel “Rum Punch” with the director’s usual touches — faded stars, profanity-laden dialogue, references to the popular culture of 1970s — but in changing the book’s white protagonist Jackie Burke to the black Jackie Brown and casting onetime blaxploitation superstar Pam Grier in the role, Tarantino made his last truly great film. Nearly all the credit for “Jackie Brown’s” success belongs to Grier, who plays Brown as a fast-thinking, sexy dynamo who’s not above roping her bail bondsman (Robert Forster) into a scam — and not below falling for him. There are other good performances in the film, including Robert DeNiro as a burned-out hood and Samuel L. Jackson as a double-crossing gun runner, but Grier owns the picture. She cons Tarantino right out of it.

Peter Joshua of “Charade,” played by Cary Grant. Another crook compelled to go legit by the doe-eyed innocence of Audrey Hepburn, Cary Grant’s Peter Joshua is the traffic cop of “Charade.” While others may be driving the action, Grant re-directs them down different streets virtually every time he shows up on screen. He’s an inveterate liar; even his name changes several times over the course of the film. And in the moments that count, you’re not at all sure whose side he’s on. No wonder Audrey falls for him.

Frank Abagnale Jr. of “Catch Me if You Can,” played by Leonardo DiCaprio. Frank Abagnale Jr. is real. The onetime confidence artist and counterfeiter passed $2.5 million dollars’ worth of bad checks in the 1960s, beginning when he was just 16. Steven Spielberg, one of the few directors to make proper use of Leonardo DiCaprio (even Martin Scorcese has guessed wrong sometimes), makes some embellishments to Abagnale’s story — for example, in the continuing relationship between Abagnale and his father (Christopher Walken). By and large, though, most of the things pictured in the film actually happened. Abagnale really did write all those bad checks; he posed as an airline pilot, lawyer and doctor; and he stole an ostentatious lifestyle primarily to meet girls.

Dortmunder of “The Hot Rock,” played by Robert Redford. Someone with Robert Redford’s good looks has no choice but to play a few good liars, and Redford has played some of the best: “The Sting’s” Johnny Hooker,” “Spy Game’s” Nathan Muir and “Sneakers'” Marty Bishop, among others. But Dortmunder is a different kind of thief and con man: He has little faith in his abilities as a liar or thief, believing himself cursed. (At one point, he even gets robbed himself.) But when Dortmunder needs to come up with a good tale to save the plan (or his own skin), he does just that, time and again. And in every single instance, he looks surprised that it actually worked.

Geoff Carter

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  1. Great choices, especially Henry Gondorff. I suggest the addition of Laurence Jameson from “Dirty Rotten Scoundrels” – Michael Caine’s suave and smooth-talking “royal” character only slightly surpasses Glenne Headly’s American soap queen.

  2. OK, I know it’s a little dated, but I’d nominate Zero Mostel in the original “The Producers”. But you called ‘em, spot on, once again!

  3. Nice. I’d also like to nominate Angelica Huston and Annette Bening as honorable mentions for “The Grifters.”

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