How to win the Caption Contest

The New Yorker cartoon editor Robert Mankoff has some advice for folks trying to win that magazine's famous caption contest, and I can't think of better tips for winning the Observer's contest as well:

1. Be funnier.
2. Enter more.

He provides some (tongue in cheek?) background on probability theory to explain how your chances to win rise the more you enter.  But the most solid bit of advice comes at the end of the piece:

"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."

You may have noticed, over the years, that many of our caption winners seem to be repeat performers. I'm guessing it's because they do what Mankoff says.

Comments

[Phil Clutts]

That advice makes sense. After sending in many unsuccessful submissions in the enthusiasm of the Monday morning moment, I learned to compose on Monday, then on Tuesday, dump, edit, or add to what I thought was clever the previous day. On Wednesday I usually dump more and tweak, occasionally adding one. Sometimes I think I am pushing your limits of patience with my multiple entries, Kevin, and sometimes I'm surprised that a submission I thought was mediocre "makes it."
They say that brevity is the soul of wit. Tough to do most of the time. I find it painful to think at length about how to keep it short. :<)
Anyway, we participants appreciate your efforts and patience with us to keep the "challenge" going each week.

[suzanne & co.]

Love the advice and I definitely follow #2...maybe more than Kevin would like!