How To Win The New Yorker Caption Contest

Robert Mankoff offers two tips on how to win The New Yorker’s Caption Contest:

  1. Be funnier.
  2. Enter more.

Since there are approximately 5,000 entries per every contest, your probability of winning is modeled by this simple equation:

X = 1-(4,999/5,000)^n

Where X is your chance of winning over time, and n is how many times you enter. If you enter the contest for 1,000 times, probabilistically speaking, your chances of winning the contest at least once go up to 20%.

This was a surprise to me, however:

By the way, contrary to conventional wisdom, your odds will also be better if you’re a woman. While some research, using college students as subjects, showed that men were marginally better at generating funny captions than women, for our contest it goes in the other direction. Yes, guys do enter more frequently; eighty-four per cent of all entrants are men. But only seventy-seven per cent of the winners are. For gals, the figures are sixteen and twenty-three per cent. Sisterhood is powerful in our contest, at least marginally so.

Mankoff clearly is invoking the “Gladwell principle” of 10,000 hours here:

While entering more, man or woman, helps, you’ll need an extra element to realistically have a shot. Which brings us back (and about time, too) to No. 1: being funnier. Interestingly, entering more helps you on that score as well. Why? Because if you have any talent for anything, and that includes captioneering, you get better by doing more of it. That was certainly true for Roger Ebert, who finally won after a hundred and seven tries, and although the evidence is only anecdotal, being pretty much restricted to the anecdote you’re reading, I see the more entries/higher level of funniness trend throughout the contest.

So, do more work, both by entering more contests and by spending more time generating captions for each contest. Interviews with winners show that they often do just that, by devising lots of captions for each contest, then tweaking, editing, and finally culling to submit the best one.

Now, shouldn’t you be thinking of more captions?

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