A recent drawing for the New Yorker’s weekly cartoon contest showed what appeared to be a lecture hall filled with ducks sitting in front of laptops. When I saw it, my first thought was of the infinite monkey theorem, which holds that a monkey, or group of monkeys, infinitely striking typewriter keys would eventually produce the complete works of Shakespeare, or at least Hamlet. Accordingly, I submitted the caption, “I hope they do better than the monkeys.” One of the three finalists selected by the judges was a much funnier and timelier version of mine: “No Shakespeare yet, but they have reproduced several Presidential tweets.” I wouldn’t call my caption a near miss, but at least it was in the neighborhood of the finalist’s ballpark.

Reflecting on the captions I have entered or come close to entering in 132 consecutive contests, I compiled my top five almost successful attempts.

Near miss #1: Contest #590, October 30, 2017

My caption, submitted: “It’s a shame he won’t be appreciated until after he’s extinct.”
Winner, second place: “It will be worth even more when he’s extinct.”

Near miss #2: Contest #559, March 6, 2017

My caption, not submitted: “I thought he’d do a cannonball.”
Winner, second place: “See? A real pirate would have cannonballed.”

Near miss #3: Contest #548, December 5, 2016

My caption, submitted: “I don’t care if you were obeying the laws of thermodynamics.”
Winner, second place: “I don’t make the laws of physics, sir. I just enforce them.”

Near miss #4: Contest #566, April 24, 2017

My caption, not submitted: “She bested the parrot.”
Winner, second place: “We’ll see how affectionate he is when he finds out who ate his parrot.”

Near miss #5: Contest #497, November 9, 2015

My caption, submitted: “I’m the little engine that couldn’t.”
Winner, first place: “She left me for an engine that could.”

I remain hopeful that, one day, I’ll come up with the right combination of words at the right time. I think I can, I think I can . . .

It’s been 10 months since my last post about the New Yorker Cartoon Caption Contest. If that sounded like the prelude to a confession, here it is: one reason I want to win, or at least be a finalist, or at the very least be a semifinalist, is that my victory (or semi-victory) could then become the subject of a blog post—and I wouldn’t have to come up with another idea for that month. So, laziness.

I have entered the competition every week since discovering it, even when I’ve been out of the country, sick, or busy with work. Ninety-six entries, ninety-five losses. (Hope springs eternal; I haven’t yet lost the current contest, though I’m well on my way.) I could try to analyze my lack of success, but why? Besides, I’ve already done that. Ultimately, the prescription must be this: be funnier, or at least cleverer.

A recent cartoon depicted Adam and Eve in the garden, before the fall (as evidenced by their nakedness). She is holding out a pie to him, and he looks concerned as he responds. I submitted the caption that was the most popular among my polled Facebook friends and was also my favorite: “Please tell me that’s rhubarb.”

This post would be very different (jubilant, triumphant, gloating) had my caption been among the semifinalists, which were as follows:

1. “Maybe we should get that to go.”
2. “Wait, we have an oven?”
3. “How much sin would some ice cream add?”
4. “What do you mean it’s your mother’s recipe?”
5. “Are the apples local?”
6. “I hope I don’t regret this tomorrow.”
7. “I’ll be damned.”

The three captions in bold type became the finalists. It remains to be seen which one will win. I voted for “I’ll be damned.”

And I will continue to pursue the popular definition of insanity: doing the same thing over and over and expecting different results.

My caption: “Is it take your dog to war day?” (Contest #486, August 24, 2015)

My caption: “The forecast said localized showers.” (Contest #478, June 8, 2015)

In March of last year, I wrote about my discovery of—and instant obsession with—the New Yorker’s weekly cartoon caption contest. I have an update: I still haven’t won. Or been a finalist. After entering 58 consecutive times. (Film critic Roger Ebert, prior to his victory, made 107 attempts; that number seemed really big 13 months ago.) A few of my efforts appear throughout this post; the winning entries have invariably been smarter and funnier than mine.

For a particular week’s contest, if your caption is among the three on which the public will vote, you are notified by e-mail—or so I’ve heard. So I was more than a little excited to receive a message from the magazine’s cartoon editor, Bob Mankoff, last Wednesday. But instead of congratulating me on my top-three submission, he was inviting all entrants to use a new ranking tool to help choose the finalists from among the 5,000 entries. Give it a try! It can be addicting—especially if you’re waiting for your own caption to come up, so you can “honestly” assess whether it’s “unfunny,” “somewhat funny,” or “funny.”

My caption: “He’s a notorious gagster.” (Contest #480, June 29, 2015)

Since I started entering, I don’t feel any closer to cracking the nut that is the New Yorker Cartoon Caption Contest. In fact, based on my failure up to this point, I feel distinctly qualified to offer advice on what not to do:

1. Don’t submit your entry early in the week, late in the week, or in the middle of the week.
2. Don’t go with your first instinct or ponder the cartoon at length.
3. Don’t embrace clever wordplay or avoid it.
4. Don’t go for the obvious or the obscure.
5. Don’t seek out the opinions of others or work in isolation.

In other words, I’ve tried everything. Of course, the best way not to win is not to enter. I won’t not be entering anytime soon.

I have become obsessed with the New Yorker’s weekly cartoon caption contest. Since the magazine’s first issue, in 1925, it has been known for its cartoons. They have even attained pop-culture status. You may recall a Seinfeld episode in which Elaine demands to know why a particular New Yorker cartoon is funny. The magazine’s editor responds, “Cartoons are like gossamer, and one doesn’t dissect gossamer.” In other words, “I don’t get it either.” The caption contest has existed since 2005. On the HBO series Bored to Death, Ted Danson’s character, George, studies the contest cartoon, on the last page of the magazine. He muses, “What would a police duck say to a suicidal bear? . . . ‘You can bear it.’ Oh God, that’s terrible. I’m never gonna win this thing.” Actually, some of the reader-generated captions are very good. Of the ones I have seen, my favorite accompanies the illustration of a woman and a clown at a sidewalk café table. The clown is seated, looking sad. The woman is standing, her wine untouched. She says, “Well, if you must know, he makes me laugh.” You can see it here.

I have to imagine that the contest presents one of the best ways for the average person to get published in the New Yorker. Still, the odds are against you: the magazine receives five to ten thousand entries per contest. (You’d probably have better luck with a letter to the editor.) And being a celebrity doesn’t help: High-profile losers include comedian Zach Galifianakis, political satirist Stephen Colbert, country singer Brad Paisley, New York Times columnist Maureen Dowd, and three-term mayor of New York Michael Bloomberg. In 2011, film critic Roger Ebert became a finalist and won, on his 107th try.

How does the contest work? The magazine publishes a cartoon in need of a caption. Readers submit their captions online. The magazine chooses three finalists, on which the public votes. The winning caption appears in the magazine, and the winner receives a print of the captioned cartoon, signed by the artist who drew it—a.k.a. my new goal in life. Is there a magic formula for getting a caption past the judges? Humor would seem to be the most important component. Contest winner Patrick House, a Stanford University neuroscientist, offers some insight:

To understand what makes the perfect caption, you must start with the readership. Paging through the New Yorker is a lonesome withdrawal, not a group activity. The reader is isolated and introspective, probably on the train commuting to work. He suffers from urban ennui. He does not make eye contact. Laughing out loud is, in this context, an unseemly act sure to draw unwanted attention. To avoid this, your caption should elicit, at best, a mild chuckle. The first filter for your caption should be: Is it too funny? Will it make anyone laugh out loud? If so, throw it out and work on a less funny one.

Chicago attorney Larry Wood, who has won multiple times, gives the opposite advice: “I think you should try to be as funny as you can.” The New Yorker’s cartoon editor, Bob Mankoff, concurs; to increase your chances of winning, he recommends, “Be funnier.” I have collected the following additional tips from Mankoff, past champions, and researchers who have studied the contest:

1. Be persistent. Enter every week.
2. Be brief.
3. Minimize punctuation, especially exclamation points.
4. Be novel and surprising. (A thousand people might send in the same caption, if it’s an obvious fit for the drawing.)
5. Be abstract, such that the picture can’t be retrofitted to the caption.
6. Use simple language.
7. Avoid proper nouns.
8. Cover everything that’s happening in the image, but don’t restate what’s in it.
9. Avoid puns and labored wordplay.
10. Keep it clean.

I have entered six times. So, who’s with me? Remember, if you don’t enter, you can’t be bitter when someone else’s subpar caption wins.