Invaluable advice from Patrick House.

Rule 1:

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.

Rule 2:

Remember that the Cartoon Editor’s Assistant is “an outsider who has never trod in the cemented garden he protects. He had to look up “urban ennui” when he arrived in New York—he didn’t learn it riding the subway for 25 years. Exploit the fact that Farley is working off the same stereotypes of The New Yorker readership as you are”.

Rule 3:

Apply Advanced Joke Theory.

You must aim for what is called a “theory of mind” caption, which requires the reader to project intents or beliefs into the minds of the cartoon’s characters. An exemplary New Yorker theory of mind caption (accompanying a cartoon of a police officer ticketing a caveman with a large wheel): “Yeah, yeah—and I invented the ticket.” The humor here requires inference about the caveman’s beliefs and intentions as he (presumably) explains to the cop that he invented the wheel. A non-theory-of-mind caption (accompanying a cartoon of a bird wearing a thong), however, requires no such projection: “It’s a thongbird.”

Lovely stuff. My favourite New Yorker cartoon btw shows a giant chesspiece in the middle of a desert, surrounded by cacti and boulders. The caption: “Interesting chess moves, #367. King’s Pawn to Albuquerque, New Mexico.”