My 5 Favorite Con-Men

Regular readers here at Longish will know that I'm more than a little obsessed with British detectives. So now, for a change of pace, let's get to know my favorite British con-men. There are a few conditions—con-men are not criminals of the vulgar sort. No, indeed; these dashing figures eschew unsophisticated fisticuffs, and make do with intelligence and witty repartee. For this reason I would not nominate Moriarty (his weapon is strategy, a general of the underworld), though I would almost nominate Saruman (disqualified because his witty repartee stems from an enchantment.)

Also, they must be loads of fun. Let's start with the most fun of them all...

1. A.J. Raffles, created by Arthur Conan Doyle's brother-in-law Ernest Hornung, was the original gentleman thief. Accompanied by his Watson, a journalist named Harry "Bunny" Manders, Raffles is a dashing cricketer by day, amateur cracksman by night.

An abundance of overdrawn, invariably foreign arch-rivals challenge the patriotic Raffles and his slow-witted biographer in their endeavors to line their pockets. And it is definitely pocket-lining that the two are after - they don’t “steal from the rich and give to the poor.” This is partly why I enjoy Raffles so much. We like him, but don't sympathize with him. He’s no white knight. In the books, there was always an uncertainty as to whether we should be rooting for or against him. This intentional ambiguity gave him an edge that Sherlock Holmes never achieved.

As for the superb 1975 TV show, it lessens the darker aspects of the Raffles character (as has nearly every adaptation, from David Niven to Ronald Colman to Nigel Havers), but also allows a sardonic alienation to satirize Raffles’s existing faults. Like the novels, these tales still operate within a decidedly moral universe; Raffles (played by a pitch-perfect Anthony Valentine), adheres to a rigid (if a bit arbitrary) law of good conduct. He is furious when a fellow thief double-crosses him, saying the man gives the criminal class a bad name. He would never dream of robbing a host (unless, of course, Raffles and Bunny are broke, in which case "we can't all be moralists, and the distribution of wealth is all wrong anyway"). It is Raffles's obliviousness to his faults (and, of course, his hilariously sympathetic attempts to justify them), that allows us to laugh off his crimes, while maintaining our moral clarity. And it is true that the series is at its weakest when trying to prop up its protagonist as a Robin Hood (as in “Mr. Justice Raffles.”)

Still, it's a marvelous show - one of my all-time favorites. The quality does vary a bit (it takes an episode or two to get into the flow of things), but it's lots of fun.

The first episode:

2. Jackie O'Shea, of 1998 film Waking Ned Devine, has all the savvy, charm, and moral sense of A.J. Raffles, though he operates on a significantly lower social scale. A resident of the idyllic, tiny Irish village of Tullymore, Jackie and his best friend Michael spend their days concocting mischief and frequenting the local pub. Their big chance comes when old Ned Devine wins the lottery and promptly dies from the shock of it. Convinced that the spirit of Ned wishes them to claim the winnings, Jackie and Michael set off on an escalating set of hijinks to pull off their 7-million-pound heist.

Like Raffles, Jackie is obviously laboring under a level of self-delusion—but because we, the audience, are in on the secret, we let it slide. We laugh with him, but also at him, and just a bit at ourselves.

The opening scene:

3. Moist von Lipwig is the creation of British fantasy author Terry Pratchett, and protagonist of hilarious TV movie Going Postal. Another morally-motivated confidence trickster, he's a work-in-progress, reforming as the story goes along. 

Collared by the Ankh-Morpork City Watch, Moist is hanged (to within an inch of his life - “the last inch is the crux of the matter”), and then hired by Ankh-Morpork’s benevolent dictator Lord Vetinari to restore the postal service. It’s a perilous task, and Moist must employ all his skills to fend off homicidal competitors, psychotic employees, and mountains of supernaturally vindictive paperwork. A smattering of British costume royalty (David Suchet, Charles Dance, Claire Foy) round out the lovely ensemble cast. 

As Moist interacts with Mr. Pump, a conscientious Golem, and Adora Belle, a cynical campaigner for Golem’s Rights, he begins to realize the everyday consequences of men living off the wealth of others. There are no peccadilloes (a word which I’ve been dying to use for years). I’ll leave it to you to draw the political conclusions.

Trailer:

4. Flambeau isn’t technically a British thief, but given that both his creator (G.K. Chesterton) and man who plays him (Peter Finch) in 1950 film The Detective, are British, I felt it was a fair compromise. Like Moist, Flambeau is offered a form of redemption through his relationship with others. This time it’s diminutive, foolish priest Father Brown, played by an owlishly charming Alec Guinness. While dated and rather slow, the film is one of the more faithful representations of Chesterton’s best-known sleuth and nemesis, and the rivalry of the two characters lends poignancy to the narrative.

5. Professor Marcus is the only crook on my list that has neither a moral compass (conditional or otherwise), nor a redemptive character arc. That’s not to say that The Ladykillers (1955) isn’t concerned with a form of rough justice, but Marcus and his gang (this is really a group nomination) are definitely the antagonists. Once again we have Alec Guinness, now playing sleazy con-man Professor Marcus. Peter Sellers, Herbert Lom, Cecil Parker, and Danny Green are his accomplices, a motley crew who try and swindle an elderly lady named Mrs. Wilberforce (Katie Johnson). Guinness hams it up shamelessly, abandoning his more familiar style of understatement. The film itself is quite subtle, not being laugh-out-loud funny but quietly tapping into the British strain of eccentricity.

If there's anything I've noticed in this list, it is that I like bad guys - but not when the bad things they do are justified by the storyteller. So over to you - who are your favorite crooks, swindlers, and confidence tricksters?

Longish