Winning the New Yorker Cartoon Caption Contest is Easy

Michael Murray currently lives and works in Toronto. He has an extensive wardrobe and is a...

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Winning the New Yorker cartoon caption contest was pretty easy for me, but then again, I’m something of a genius. Maybe not an “IQ genius,” like some other thinner, bookish people, but all the same, I have my own sparkle. My mother assured me that, ever since that bee stung me in Niagara Falls on my 24th birthday, I’ve had a special quality about me, something almost luminous. “There was a touch of the divine in that bee poison,”  she said, “you’ll always be a ‘petit cerveau’ to me.”

You probably want to know an awful lot more about me, about my journey from bee sting to crafting the perfect cartoon quip, but I don’t want to bore you with the details of how I struggled academically, professionally, athletically and romantically before rising to the top in one electric flash, when I, Michael Murray, won the New Yorker cartoon caption contest.

Let’s just concentrate on the victory so that I might be able to inspire you to similar heights, for truly, in our hearts, is the New Yorker not the summit to which all our hopes ascend?

My caption was for a cartoon that had two grizzled cowboys riding through a desert. One of the cowboys was on a horse, the other a giant insect. The cowboy on the insect appeared to be speaking to the other guy in a nonchalant way. I looked at it and thought, “On a clear day, I can get Santa Fe on the antenna.”

This won.

After several weeks I was sent an unimpressive copy of the cartoon with my caption on it, upon which was a yellow post-it note in which Farley Katz, the artist, exclaimed, “Great caption!”

I have to admit, conquering the world was a little anti-climactic.

However, should you wish to scale the same mountain I would suggest thinking of the New Yorker as the literary equivalent of a looming, Soviet monument. The magazine towers over us, an intimidating and unalterable center of culture and aspiration. The presence of the New Yorker never lets us forget how small we are. Whimsical? Sure, but it’s a stern kind of whimsy. We are what the New Yorker needs us to be. There are rules and the rules must be obeyed, and if you want to win the contest you’re best advised to forget about writing the funniest caption and settle instead for one that will be fresh and surprising, but only within a very familiar and limited cultural context.

You have to work within the construct of the urbane sophisticate. Think of the New Yorker as your client, and your job as reinforcing a powerful, century-old brand. The material is always subordinate to the overarching personality and agenda of the magazine. You can’t drop the names of politicians, celebrities or companies into your caption, for that would be gauche. You’d best avoid puns, too. They’re too British, and Americans can only tolerate British humour as translated through Canadians, as the Brits made them pay taxes, which is something Americans completely fucking hate.

So your client wants to broadcast a particular, magical kind of Manhattan culture out into the world, a verbal distillate of one of those Woody Allen movies from back in the day that doesn’t really exist in time. The New Yorker has a subtext of nostalgia, and it will never truly have a youthful spirit, so don’t try to reinvent the caption wheel (I have tried both profanity and writing in Japanese script and neither worked), as it will only bring misery and frustration to your house. You have to be hip in your verbal configurations, but only in a “cool dad” kind of way. You should be beyond fashion. As for all its urbanity, the New Yorker is really about domesticity and the small, tender chores that orbit it, rather than the feral prowling of cupcake-baking Lena Dunham acolytes.

Think gentle melancholy, think small, think (New Yorker) familiar, but think smart, and always pay attention to who is speaking in the cartoon. The caption has to make sense of the visual narrative, so even if the “subject” isn’t in the dynamic position in the cartoon, the caption still has to emanate from that source. It is a rule. If you do these things, you will have a good chance getting past the first gatekeeper and be made a finalist, and then, well, then it’s up to the voters, and if the gods smile, all glory—in the form of an unimpressive copy of the cartoon with an insincere post-it note stuck to it—will be yours.

As preparation, I am providing you with one of my wife’s doodles that I found stuck to the fridge. The person who submits the most New Yorker-esque caption will receive a vividly orange baseball hat straight from Cuba—it was blessed in words that I did not understand by a woman smoking a cigar, so it is sure to bring good luck. This is the cartoon:

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