Expert reveals tips for winning The New Yorker cartoon caption contest

I am not in any way obsessed with The New Yorker caption contest each week. I swear. I like to submit my cleverly constructed witticisms (which have — shockingly — never been selected), but in no way does this cause me to put the rest of my day on hold 'til I have the perfect caption.

This essay in The Atlantic by a guy named Lawrence Wood, the self-described Ken Jennings of the caption contest, looks at his one true love: 

I have spent much of the past 25 years obsessing over that magazine's cartoon-caption contest, in which readers compete to supply the cleverest line of dialogue to a captionless drawing. I have entered more than 900 contests, losing almost all of them. But, because I have won eight contests, and made it to the final round in seven others, I hold the all-time caption-contest record. And I might have some insight into how you can beat me at my own game.

He goes on to let us in on some tricks of the trade, though in some ways it's like trying to describe inspiration and how to find it — you either got it or you don't. 

A particularly effective tactic is to think of a familiar turn of phrase that takes on a new and humorous meaning within the context of the cartoon. One contest featured a drawing of what appears to be a lawyer engaged in settlement negotiations on behalf of a dog. I thought my entry—"He'll negotiate, but he won't beg"—was pretty good, but it came in second. The winning caption was superior: "My client is prepared to walk."

Those made me chuckle. And "chuckling" seems to be the goal. I often find the captions "clever" but not really "funny" and have often wondered whether that was actually the point, the sweet spot to winning. 

Should your caption be funny? Perhaps surprisingly, there's some controversy around this point. In an article for Slate published not long after I won my first contest, Patrick House, a Stanford-trained neuroscientist who won Contest No. 145, cautioned against submitting anything genuinely laugh-out-loud funny. To do so, he argued, would discomfit the neurotic, introverted New Yorker reader. "Your caption should elicit, at best, a mild chuckle," he wrote.

Aha! Verification of my theory from an expert. That must be why I've never won — my captions have just been too damn funny.
There's more insights, particularly about cursing and profanity, if you read on. And if you've never tried the contest, I highly recommend it.

The New Yorker editor's excuse for inviting Steve Bannon to headline its festival works for every New Yorker cartoon