"I think what makes someone good at writing captions is the ability to be very free in their thinking. Humor is essentially a type of play. If you try to solve this like you would answer an SAT question, you will fail. Part of it has to be loosey-goosey. When you look at one of these things, you have to let your mind be free, let your unconscious or subconscious do the processing. You can’t go through enough possibilities... It’s funny. Maybe I’m going somewhere in a cab or giving a speech, and somehow it’ll come up that I am the cartoon editor of The New Yorker. People will come up and show me their caption and say, 'Honestly, was my caption not better than the ones that won?'"But the best explanation of the ineffable humor behind a good New Yorker cartoon was on Seinfeld:
Elaine: Well boys, I did it. I had to stay up all night but I finally came up with a great New Yorker cartoon. Pretty good? Well uh! This is a gem . Kramer look it....(Kramer stays silent).....What? It's funny. Jerry: It's a pig at a complain department. Elaine: And he's saying " I wish I was taller" ha ha. See? that's his complaint. Jerry: I get it. Elaine: Do you!!!.. because that's not a normal complaint. Jerry: How 'bout if it was something like " I can't find my receipt, my place's a stye. Elaine: Everything with you has to be so .. jokey. Jerry: I'm a comedian. Elaine: I wish I was taller, that's, that's, that's nice. That's real. Jerry: Well I got a complaint. This cartoon stinks.