Unfunny

I was, for much of my life, funny. More than funny. I was a card, a hoot. I could genuinely crack people up. And it wasn’t a desperate kind of humor, either. I didn’t urge my funniness on others the way some people do, constantly nagging their friends with jokes like a party host who insists that you try the clam dip. No, I was low-key, patient. But whenever a situation called for humor, I could absolutely deliver. I had wit and precision and timing—the whole package. I had moments of excellence.

Once, at a social event, I found myself cornered by a financial-services professional, a real windbag, who had a theory that the world’s great thinkers were all crypto-capitalists. Socrates, Descartes, Spinoza, Kierkegaard, Emerson—they all believed in the supremacy of money, he insisted. “Do you know what Thoreau would say if he were alive today?” he asked. And with no forethought whatsoever, I arched an eyebrow and responded, “‘Most men lead lives of quiet depreciation’?” The delivery, you understand, was perfect—dry and restrained. It was one of those moments that matter, if you’re someone who likes being funny. At such moments, everything is effortless and right. Being funny feels easier than not being funny. Your swing is as pure as DiMaggio’s.

I’m not very funny lately, which is not to say that I won’t be funny again one day. But right now I’m experiencing what Saint John of the Cross, if he’d had a different set of priorities, might have called the Unfunny Night of the Soul. Funniness won’t come. I can offer up a clever remark every now and then, but it feels too deliberate, too methodical. It requires effort, like conjugating French verbs. And since humor has everything to do with spontaneity—since a genuinely funny moment is always created suddenly, miraculously, like a particle of antimatter—it’s not fair to count the carefully practiced lines. The fact is, I’m empty.

The cause of my drought, or at least the thing that inaugurated it, is The New Yorker’s Cartoon Caption Contest. I don’t know whether other funny people have been undone by this weekly feature, but its effect on me has been devastating. Every Tuesday, I turn to the back of the magazine, survey the new cartoon-sans-caption, and try to fill in the blank; that is, I try, like thousands of other readers, to create the line that belongs there, the quip that seems not just funny but inevitable, a kind of Platonic reconciliation of picture and words. The cartoons are usually wacky—say, a man walks into a bar with a duck on his head, or a defendant stands before a courtroom judge wearing only scuba gear—but the challenge is to create a caption that is as urbane as the magazine itself. (Other publications, like the un-urbane Parade magazine, have cribbed the fill-in-the-caption idea, but they seem to be looking for lines that are merely funny, not celebratory of what’s funny, not rooted in an ideology of funniness. In other words, they’ll settle for gags.) I approach each week’s cartoon carefully, reverently, marshalling my wittiest energies; I stare at the cartoon for tens of minutes, almost without blinking, like a superhero trying to engage his X-ray vision. But alarmingly—absurdly!—I come up with nothing. Or worse: I create great heaps of unfunniness, captions that might be described as humor byproduct, the spent fuel rods of humor. I become convinced, finally, of the impossibility of the whole project. Really, what can a bartender say to a man with a duck on his head? The question starts to seem more like a Zen koan than an actual problem to be solved. Desperate to salvage the experience, I offer the poor bartender the only words I can think of (“Wow—you have a duck on your head!”), submit them, and mourn my lost talent.

I have, of course, spent time trying to understand my failings. At one point, I gave...