Want to win the New Yorker's cartoon caption contest? The first rule: Don't be too funny. So says recent winner Patrick House, who lays out his can't-miss strategy in Slate. Keep in mind that reading the New Yorker is an introspective pursuit, one of "lonesome withdrawal." Which means that someone on the train probably doesn't want to guffaw out loud. Aim instead for a "a mild chuckle."
Skip the puns and obscure references. Make it a "theory of mind" caption—that is, "project intents or beliefs into the minds of the cartoon's characters." Know that your first gatekeeper is a twentysomething former roller-coaster operator. And because the victor is determined by online vote, shelve your shame and get everyone you know to vote.