Every week, a New Yorker cartoon is posted online and printed in the magazine without a caption, and thousands of people write in with their suggestions. Readers vote on a winner, and the top pick is printed in the following issue. Willy Staley and Matt Jordan submit a caption pretty much every week, working as a team. They’ve been doing it for years, but they never win—and they probably never will. Their goal isn’t to write a winning caption; it’s to write the most wrong-headed, vulgar, and hilariously inappropriate caption possible. “There’s something to the typical New Yorker cartoon,” says Jordan. “It’s succinct, it tends to be clean, it tends to be on cue. We just try to curveball around that.” Using their failings in the official contest, they’ve built an online following for their Tumblr blog “Shitty New Yorker Cartoon Captions.” They sat down with The New Yorker’s cartoon editor, Emma Allen, to discuss what separates a typical losing caption from a truly shitty one.

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“What did the council decide on item 42?” — answered with the speaker and the moment.