About twelve years ago, a teacher hired me to draw a caricature of her colleague as a gift. The colleague, she mentioned, was a New Yorker cartoonist. I said yes immediately, then realised I had no idea what the man looked like.

That’s the whole profession, basically. You know the work, you know the signature, you’ve never seen the face. “It’s the perfect crime,” Avi Steinberg said this week, a decade after drawing him without his knowledge. “You can be famous on paper and still walk around without anyone bothering you.”

Avi kept the caricature. I look at it and see only the mistakes, but he tells me it’s a treasured possession. I’m deciding to believe him.

Ten years, Ten a week.

Avi started submitting to The New Yorker straight out of high school and sold nothing for roughly a decade. I asked whether he hit year seven and wondered if he should pack it in. “I don’t wait till year seven to feel like that…”

The turn came when he worked out what the cartoonists he admired were actually doing. “The greats, they drew a batch of ten cartoons every week. And when I really learned that, my heart sank.” So he gave himself a year of ten a week. No more emotional rollercoaster. At the end of it, he could either do this properly or quit.

He teaches kindergarten in New York City, which is where he gets his best material on artistic confidence. “My students are the best artists in the world. No one told them how not to draw something.”

I told him about being fifteen, getting detention for a savage caricature of my history teacher, then having that same teacher sidle up to my desk during detention and offer me twenty dollars to do a mean one of the retiring school gardener. Avi diagnosed the whole career in one line: being a cartoonist is the balance of being in detention and getting twenty dollars.

Paid to be in trouble. Still true at forty-two.

Then , our official ‘Ryan Seacrest of Comic-Con’ gossip elbowed his way in to the stream

Tom appeared halfway through, still wearing his San Diego Comic-Con lanyard, having got home at half one that morning. He would like to be appointed my official Comic-Con Correspondent. Granted, obviously.

His collection And To Think This Started As A Book Club was up for an Eisner. Then the winners leaked. Comic-Con briefly posted the results on their own website, somebody screenshotted it, and Reddit did the rest. “Not since the Will Smith slap of Chris Rock has there been such a scandal at an award show.”

Tom resisted. Tom failed. He looked the night before, reasoning he would enjoy the dinner more if he knew, and found he had lost to Tom Gauld, “who has the flawless first name of Tom.” He was there with his son and struck a deal: every second book sale converted directly into Pokémon cards. “I basically started asking for payment in Pokémon cards, because that’s what it would be anyway.”

Tom is also up for Gag Cartoonist of the Year at the Reubens, after a Thurber finalist nod and the Eisner. He is hoping to lose all three. “I think it’ll be funnier to go 0 for 3 than 1 for 3.”

Rule of threes. The man is committed to the bit.

Avi’s new book contains an alien character he invented at twelve, posted to the newspaper syndicates, and had rejected. He kept the file for thirty years. “Nothing is ever totally gone. It was very nice to see that the work I did as a twelve-year-old wasn’t a waste.”

He is also banking the small milestones as they arrive: the cover, the proofs, the first box of copies. “However the book sells, whatever the reception is, those things are yours.”

Tom’s verdict on his friend, delivered with real affection: “Avi is like the Aristotle of gag cartoons. Your stick figures coping with the horror of existence is one of my favourite things.” Avi: “My biography.”

Preorder Now!

Watch the replay, then buy the books.

The full episode is up now. There is live drawing in the back half, and Tom talked his way out of it by claiming he cannot sketch, which I am choosing not to believe.

Avi Steinberg, The Jumble is out 3 November and available to pre-order wherever you buy books. Pre-orders genuinely matter: they all tick over on release day and become the number the publisher looks at.

Tom Toro, And To Think This Started As A Book Club, his Eisner-nominated collection, is out now. His children’s book Between the Balloons lands at Thanksgiving and is also up for pre-order.

Buy them from bookshop.org, from your local, from all of it. As Avi put it: buy one from each place, just to spread it around.

‘til next time!
Your pal,

PS. I am up for a Reuben this year in book illustration division for You’re Not a Real Dog Owner Until, drawn with Scott Dooley, alongside two books I own and rate more highly than my own. Morris remains unimpressed, and has been on the drafting table chair since Tuesday.

PPS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

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DMA#55: Paid to be in trouble with Avi…