Writing Jokes With Robert Leighton (The New Yorker)

How has your time at Northwestern influenced the rest of your career?

While I was at Northwestern, I did a number of things that regularly put my work in front of my peers. In particular, I edited the humor magazine and I drew a comic strip for the school paper. I knew my audience was smart and sophisticated, and I would hear (directly or through the grapevine) whether my work was hitting or missing. I had a lot to learn, and still do, but some part of me is still imagining that Northwestern audience out there.

Are single-panel cartoons more difficult to produce than cartoon strips? (Why or why not?)

In retrospect I think writing the comic strip was easier than coming up with single-panel cartoons. Over my four years drawing “Banderooge” at Northwestern I developed a cast of characters, each with his or her own voice. To some extent the characters began to write the strip themselves because of the ways their desires clashed.

In creating single-panel cartoons (I hate the term “gags”), you are dreaming up an entirely new scenario each time, and trying to imbue the players with enough signals so that the humor comes through: This kind of guy saying thatkind of thing to that other sort of person.

What makes a single-panel cartoon particularly effective?

My favorites (whether my own or by others) have an incongruous visual element that is resolved by the caption. Reading a cartoon happens over a number of almost imperceptible steps. First, because the visual elements register effortlessly, I think you glance at the drawing just long enough to think, “Oh, it’s cavemen admiring a cave drawing” or “Oh, it’s two frogs, one of them has a paddleball,” but you don’t understand what you’ve seen until you read the caption, which ideally should cause you to look again at the picture. And then the incongruity in the picture should cause you to want to read that caption again to enjoy it more fully. Back and forth and back.

Do you have any themes or motifs that you especially enjoy?

I think I’ve sold more cartoons about cavemen than any other topic, so I must find them a rich area to contemplate. Of course, a caveman cartoon isn’t usually about cavemen at all. It’s about relationships, or snobbery, or whatever — you’re just presenting it in a caveman motif.

I do like to write cartoons about childrearing. But again, that theme is woven into cartoons that might appear to be about bullfighting or evolving fish or what-have-you. I don’t have a ton of drawings depicting Mom and Dad raising the children.

How did Puzzability first come together?

My first job out of Northwestern was as an editor at Games Magazine. This was really a dream job for someone like me. That magazine was an extremely creative, playful publication with a staff that rivaled The New Yorker for wit and intelligence (they had no business hiring me; I had never written a puzzle in my life). Some years down the road, the magazine fell on hard times and many people associated with it scattered to the winds. I reached out to some of them to form our own puzzle-writing company. I’ve been lucky in that I’ve always worked with people who pushed me to stretch what I could do.

How does one become a puzzle writing expert?

I’m no expert. But I know when I’ve done something good, and so instead of your question I’ll answer this one: “How does one get to be someone who can write a good puzzle?” It’s a craft like any creative endeavor. You work at it constantly, you develop a vocabulary of ideas you’re comfortable with, and you combine those ideas in new ways just to see where they take you.

An odd thing about writing a puzzle is that you need someone else to test-solve it to make sure it works. If it needs refining, your tester (which in my case would be one of my co-workers) needs to retest it “dumb” — that is, pretending that they don’t already know the solution. Those notes, and that refinement, help you anticipate problems for next time. Puzzle writers want to give their audience just enough to solve the puzzle, but no more than that.

How cool was it to work on Mr. Robot?

Recently Puzzability has worked on a number of cutting-edge projects; one of them was a Mr. Robot tie-in book. The project was very cool to work on, particularly when we got the call, because we were told the season’s big reveal before anyone else. If you watched Season 2, you know that Elliot was keeping a diary while he was in prison. But meanwhile his alter-ego, Mr. Robot, was trying to break him out.

Elliot was unaware of the plans of this other part of his psyche. A writer on the show’s staff wrote the meat of the diary, but Puzzability was brought in to craft hidden messages that Mr. Robot was sending to, and receiving from, the outside world. They had to be accessible enough for readers to find them, while being so well hidden that Elliot wouldn’t recognize them as codes. And Elliot is a brilliant hacker, nobody’s fool, so it was a fine line to walk.

The ‘Red Wheelbarrow’ Tie-In Boo

The book was produced to look exactly like a composition notebook with pencil handwriting inside. But there are also tipped-in items that look like prison artifacts, and we created many of those. One of them is a photocopied list of bible quotations that Elliot was given in his mandatory prison bible class. There’s a code hidden in that, but Elliot just tucked it into his notebook and never gave it a second look. Mr. Robot figured it out, and so did readers.

That is awesome (thank you for sharing). Generally speaking, what makes for a good work space?

I’m the wrong one to ask. I feel like I can work anywhere. My puzzle work is definitely augmented by computers and occasionally graph paper, but a lot of the noodling (and cartoon-writing) actually happens while I’m walking. It’s good to have the Notes program on my phone for ideas that have to be written down. I don’t rely on having a clean surface or perfect silence, although yes — I do prefer those to their opposites.

I also just grab the blank side of scrap paper to work out ideas for cartoons. I used to do them in sketchbooks but they began to feel too “precious.” I prefer the throw-away nature of working on scrap paper. It’s liberating.

Why do you think cartoonists become cartoonists?

I don’t think that cartoonists ever decide to become cartoonists. I think they just don’t decide to become something else. I think that when we are little we are instinctively creative and open about the world, and we can’t draw all that well, and we think the world we see is confusing and adults are dumb, and all that stuff. And we simply continue along that path until we learn how to draw better. Then we’re cartoonists.

What makes you laugh?

Something really, really clever. It doesn’t even have to be funny per se. But if it’s just so carefully thought-out and well-realized that I never could have thought of it, it’ll elicit laughter. From a Buster Keaton sight gag to a wonderful anagram. It tickles my brain (I don’t necessarily laugh out loud, although that happens, too). As a cartoonist slash puzzle-writer, I get those reactions all the time. Nice way to spend the day.