"Humor and victory are different matters entirely. To understand what makes the perfect caption, you must start with the readership. Paging through The New Yorker is a lonesome withdrawal, not a group activity. The reader is isolated and introspective, probably on the train commuting to work. He suffers from urban ennui. He does not make eye contact. Laughing out loud is, in this context, an unseemly act sure to draw unwanted attention. To avoid this, your caption should elicit, at best, a mild chuckle. The first filter for your caption should be: Is it too funny? Will it make anyone laugh out loud? If so, throw it out and work on a less funny one."
Patrick House in Slate offers advice as to how to win The New Yorker Cartoon Caption Contest.
And on his blog, Daniel Radosh offers advice as to how to win his Cartoon Anti-Caption Contest.
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