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The vast, intricate conspiracy of the New Yorker caption contest

A cover of The New Yorker.

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An immaculately coiffed lion in a Don Draper getup is visiting a caged lion friend at the zoo. Try making sense of something like that. Or of a businessman talking to his secretary with a fully grown crocodile resting belly-up on his desk.

I am a regular contestant in The New Yorker Magazine's Cartoon Caption Contest and every week for the past 117 weeks I have wrestled with bizarre cartoon images just like these. Along with many thousands of other contestants from the United States and Canada, I attempt to supply the missing caption that best exemplifies the sophisticated humour of The New Yorker.

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Although I have not yet been even once among the three weekly finalists, my optimism is undiminished.

If nature calls at around 2 on a Monday morning – as it often does – on my way back to bed I will stop off at for the freshly posted contest results and the coming week's cartoon challenge. For the rest of the night I will try not to think about that bedridden Neanderthal man with the multiple intravenous lines, or Groucho Marx in the form of a thundercloud delivering the Torah to Moses.

At work on Monday mornings, I attribute my fatigue to weekend-long Iron Man training sessions.

Although not entirely without merit, my earliest efforts were quirky and unwieldy affairs. I was disdainful of my family's constructive criticism, particularly my wife's weekly verdict: "It's really funny, but I don't understand."

About a year ago, I was buoyed by the enthusiasm of friends for my caption, "I bought it on the chopping channel." The cartoon depicted a living-room scene with a hostess, two guests and a full-size guillotine standing in the corner. But "chopping channel" did not make the cut, and those same friends have never allowed me to talk about the contest again.

To them, my single-mindedness must suggest one of those newly minted psychiatric disorders we've been hearing about lately – the ones that allow you to function, but not very well. My friends have had enough, but I clearly haven't.

"Chopping Channel" was arguably my very best submission to date. In the wake of that devastating defeat, I have crafted a perfectly rational conspiracy theory. Like many desperate men, I spend far too much time on the Internet and, late one night, I learned that the contest's editor and chief judge shares my loopy and exceedingly rare given name.

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The U.S. Census Bureau reports that in 2000, only 0.008 per cent of all newborns were named Farley. As a baby name, Adolf has exactly the same popularity quotient. I sensed a problem. Could it be that to avoid charges of name nepotism I am being vetoed and doomed to the wastebasket of cartoon history?

But a conspiracy theory is not going to get me on the inside back page of The New Yorker. Realizing this, I have since pored over the contest's archives and familiarized myself with its voluminous theory base. The result is a more analytical approach.

Most past winners advise against the use of superfluous punctuation. Periods and question marks may be unavoidable, but exclamation marks are regarded as the kiss of death. I avoid apostrophes anyway, since I tend to put them in the wrong places.

Research shows that any mention of brand names is not a good idea. One cartoon of a man showing off a room full of grand pianos prompted my caption: "It's the Costco Party Pack." I'm a lot wiser now.

Brevity, even more than levity, appears to be the hallmark of a successful caption. A random sample of 20 recent winners suggests the ideal caption contains 8.7 words. In my quest for minimalism, I have submitted a few one- and two-word captions that were so cryptic I didn't understand them myself.

My most impressive tactic is a nifty little theory borrowed from neuropsychiatry – something called "Theory of Mind". TOM skills are a lot like everyday empathy, allowing us to enter the minds of others and grasp what they are thinking.

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It's not easy, though. The cartoons of The New Yorker regularly feature cats, walruses, crustaceans and, most recently, an unhappy-looking serpent with a curvaceous and distinctively humanoid tush. Personally, I've done some very good work with poultry.

For driven participants like me, the contest's lure is the promise of narcissistic gratification – the second-best kind.

In a recurring fantasy, I am sitting in the lobby of Manhattan's Algonquin Hotel. Opposite me sits a thirty-something version of the late Susan Sontag, a woman of dark, smouldering beauty and an icon of 20th-century intellectual life. The martinis are dry and it's late afternoon.

We chat about her celebrated essay "Against Interpretation", and my sublimely amusing caption in a recent issue of the New Yorker.

As for my lions, the one in the Brooks Brothers suit is saying, "We miss you at the office but Human Resources Department does not mean all you can eat." That could have been a winner, but it's 8.3 words too long.

Farley Helfant lives in Toronto.

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