My First Cartoon in the New Yorker 

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This was my first cartoon to appear in The New Yorker magazine. I submitted it in May 2021 and it appeared in the December 6th, 2021 issue.

At the time I drew this, two-factor authentication was getting more and more common when logging in. What might authentication look like in ancient history? The idea of a flying rock with numbers or symbols on it replacing a text message seemed funny to me. A fort on the outskirts of the Roman Empire was a good setting (and the background would be easy to draw). I used Google Image to find some examples of wooden Roman forts.

Thumbnails and ideas for the faces, poses and props (especially the little ‘cart of wares’).

I started by sketching in a notebook with a blue ballpoint pen. The original caption idea is at the top of the page and, surprisingly, it’s pretty close to the final version.

The thumbnail sketches are all pretty much the same but I moved the catapult, flying rock and the guard around to see what composition worked best. I went with the thumbnail in the lower right .

I had to pick a number. The drawing needed six or seven characters to look good. In Roman numerals that equates to a number in the thousands. 2527 had a nice mix of M, X, V and I, and it’s the PIN number for all my bank accounts and health records. (Nah! I actually made sure the number didn’t have a special significance for any group.)

I moved on to pencil sketching with a #2 pencil on printer paper. Keeping the paper in portrait mode keeps me from letting the drawing get to wide… horizontal cartoons don’t work as well in the magazine format.

Pencil sketch. For the composition, I imagined a large circle around the whole thing and you can see that lightly sketched in in the background.

This is the step where I’m most worried about messing the idea up and ‘locking in’ to a composition that doesn’t work. I try to have the mindset that I can throw it away and start over. Sometimes I draw a new line then reach for the nonexistent ‘undo’ button. Lots of erasing. It usually takes about an hour to get to a point where it feels ready.

Scanning the pencil sketch lets me fine tune the drawing without sacrificing the spontaneity of the pencil sketch.

The pencil sketch is scanned and opened in Photoshop. I move, resize, rotate, and tweak elements of the drawing (Edit -> Transform -> Distort is my best friend). The location of the catapult arm and the flying stone were really important and being able to position them digitally was a big help. At this point, it looks really ugly, but everything is where it should be.

The digital image above is printed and taped to the back of a piece of Bristol paper. A light table lets me see the lines as I ink the drawing. This technique is nice because there are no pencil lines to erase. Most of the inking is done with a dip pen. It’s hard to control the dip pen and that’s a good thing… there’s lots of variation in the lines. For this drawing I used a Micron 005 for the wood grain. For the ink wash I use an Aquash Watercolor Pen filled with an ink/water mixture (‘Aquash’ is a weird name). 

Final artwork done with a dip pen, a Micron .005 for the wood grain, and an ink wash.

The finished drawing gets scanned at 600 ppi greyscale. Back in photoshop, the Level tool is used to make sure the whites are white, the blacks are black, and the grey just looks right.

The New Yorker accepts batches of up to ten cartoons on Tuesday mornings. If they decide to buy one, they let you know Friday afternoon. When I have a batch submitted it’s hard to think about much else on Friday…just keep refreshing Mail and watching for “O.K.” in the subject line. 

The editor liked the little ‘cart of wares’ the character at the gate was dragging and I have to admit I enjoyed drawing that detail the most.

Honestly, I’m not sure what the grey thing near the back is. I think I was going for a sack of grain but it came out more like a hat or a loaf of bread, or a hat made out of bread.

After they buy a cartoon and the artist sends in the final artwork, it can be a year or more before the cartoon runs in the magazine.

My first hint that the cartoon was going to be printed was receiving this email near the end of November:

The copyeditor asked for these changes for one of your cartoons.


"We sent you a secure access code! Do not share this code with anyone! Your access code will expire in 10 minutes!"


"We sent you a secure access code! Do not share this code with anyone! Your access code will expire in ten minutes!"

Sound OK to you?

You bet it sounded OK with me! Two weeks later the cartoon ran in the magazine.