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:
- Be funnier.
- 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."