Even celebrities find winning the “New Yorker” caption contest hard

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The New Yorker cartoon caption contest is notoriously tricky to win. Beyond the fact that there are surely many entrants each week, there's also the extremely particular science behind the humor that wins — as has been noted before, often writing the flat-out funniest caption will instantly guarantee you runner-up status. So don't feel too down if you've never managed to do it. Heck, just look at how many publicly beloved (or at least acknowledged) figures have never won, even though their celebrity status could theoretically garner them votes. According to the Wall Street Journal:

The six-year-old contest, which appears in the back of the magazine every week, has dogged best-selling authors, Pulitzer Prize winners and business tycoons. Michael Bloomberg, self-made billionaire and three-term mayor of New York, has been heard to complain that no matter how hard he tries, he can't even come up with a contender.

A contest from 2007 showed two dogs talking as they watched another dog poised to throw a stick. One of the 7,807 submissions for that cartoon came from [Zack] Galifianakis. "Big deal. I can DRIVE a stick," he wrote. The caption was passed over in favor of the winner, "He's his own best friend." The actor hasn't entered the contest since.

Other frustrated big names include Maureen Dowd, singer Brad Paisley, and British authors Bernard Cornwell. Perhaps the most notorious is Roger Ebert, who entered the contest 107 times before the internet mobilized to vote his 108th entry into the number one spot. But considering the, uh, sometimes "inscrutable" nature of the top submissions — to put it sort of kindly¹ — maybe the fact that it took him so long to nail it should reassure him that he's actually doing something right.

¹It's true, though. Sometimes the winners are good, and sometimes the winners are… interesting? Let's say interesting.