What I learned from Bob Mankoff

The winding path from Perth to the New Yorker’s pages.

Jason Chatfield
The Walkley Magazine
6 min readAug 4, 2017

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My relationship with The New Yorker started when my aunt bought me a subscription for my 21st birthday. It was an education getting to know the humour and the taste of the cartoon editor. The gatekeeper. The oracle. Bob Mankoff.

The art of writing and drawing the perfect cartoon is a years-long, sometimes decades-long process of learning and rejection. Surgically finding the delicate marriage of perfect word economy and perfect line economy. Oh, and hopefully making it funny.

Today I continue my New Yorker subscription in Manhattan, receiving it each Wednesday as it’s released instead of waiting three weeks for it.

In November 2014, I woke to a message from fellow cartoonist Dan McConnell. He was flying in from Seattle to submit cartoons to The New Yorker. The conversation quickly escalated from “Let’s catch up!” to “I dare you to put 10 cartoons together and come submit with me on Tuesday!”

I spent the next two days scribbling gags, then madly honing them. I wrote and re-wrote punchlines, agonised over words and punctuation. I barely slept. All my brain could do was think of gags. My couch became a psychiatrist’s lounge. My toilet tank became a water cooler. The sneakers dangling off the power lines outside became Manolo Blahniks.

I didn’t feel finished, but settled on a final six to submit, and hurtled uptown on the F-train for one of the last submission mornings at the Conde Nast building at Times Square. The grumpy gentleman at the security desk broke into a smile when I said I was submitting cartoons to The New Yorker. He laughed at three out of six.

On the 20th floor, the walls were lined with old New Yorker cartoons and covers: Blitt, Steig, Getz, Addams, the great James Thurber. More people poured out of the lifts, including my friend Dan, portfolio in hand.

Finally, the lift doors opened to reveal a tall, curly grey-haired gentleman in sneakers, jeans and Google Glasses. Bob Mankoff, the New Yorker’s cartoon editor of almost 20 years.

The Cartoon Lounge was like a doctor’s office full of neurotic gagsmiths. I sat in the corner and eavesdropped, nervously ordering and re-ordering my cartoons. A grey-bearded man in his early 80s sat calmly across the room, a framed cartoon on the wall behind him signed S.Gross. Dan popped his head in and said, “Oh, hi Sam! I didn’t see you there. Jason, meet Sam Gross.” I had been looking at the man himself. One of the most prolific New Yorker cartoonists ever published.

Cartoon by Sam Gross

Before I could say anything, assistant cartoon editor Colin Stokes called me into Mankoff’s office. I broke into a sweat and darted a look at Sam. He raised his eyebrows and said: “It’s ok. I’ll go.”

A few minutes later, Sam walked out and said, “You’re up, kid!” I walked in, nervously clutching my pile of scribbles.

“You’re new, aren’t you?” Mankoff asked. I just nodded silently and gulped. He told me there are two kinds of New Yorker cartoonists, Word-Firsters and Doodle-Firsters, and asked which I was.

“I guess I’m a word-firster. I write the gag first, then draw the doodle.” The DickJoke Restraint-O-Meter® was off the charts.

He picked up my first cartoon and studied it. Nothing. Next one. “Hmm.” I don’t think I breathed until he stopped on one. The cartoon showed neighbours staring overhead at a pair of Manolo Blahniks dangling from the power lines.

“See, this one is good, but it’s too obvious.” I finally exhaled. “You need to let the reader arrive at the punchline without writing it all out for them. Let them solve the riddle themselves.”

He moved on. “We try and stay away from the ‘cartoon grotesque’, where you’ve drawn the old lady as a kind of caricatured version of an old, decrepit grandmother. If you just draw a regular old lady it can be just as funny, and it isn’t distracting. The punchline should do most of the work.”

He stopped on the next one. “Hmm. Toilet humour … No.”

He looked at the final one and stacked them back together, pausing to consider his next words.

“The way you wear your hair, it’s a conscious decision. It’s a style you’ve seen somewhere, at a party or in the streets or with your friends … you’ve decided, that’s the way I’ll wear my hair so I’ll fit in or I’ll look a particular way, right?”

I nodded like I knew where he was going with this.

“When you decide how your work looks, whether it looks like everyone else’s, or it’s completely unique and distinct, you’ll stop being so preoccupied with the look of the thing and just focus on the thing itself, what it needs. You don’t need to be a great artist to do a great cartoon. There are lots of artists who work for us who aren’t great artists, but they include just what the joke needs and leave out the rest. You should work on finding that balance.”

He told me he was happy I’d started submitting and asked if I intended to continue. “If you’ve been paying attention, you’ll notice we’ve started publishing a lot of new cartoonists in the magazine.” He gave me a big smile and raised his eyebrows, showing me the door.

I slunk back to the cartoon lounge, rejection slip in hand. Lamb after lamb went to the slaughter. My spirits were lifted as Sam Gross scribbled a note on the back of my rejection slip. He was inviting me to the legendary post-submission cartoonists’ lunch: a decades-old New York tradition.

If you’ve ever had the joy of hanging out with comedians or cartoonists, you’ll see how they analyse the world in the most incredible detail. They dissect every little part of everyday life in a forensic way, taking great joy in finding absurdity in the quotidian. The afternoon passed in a happy blur. I stood in awe of how quickly it had all happened.

I would definitely be doing this again. And again …

Epilogue

This story has a happy ending.

Two years later, on Bob Mankoff’s final day as New Yorker cartoon editor, he purchased one of my cartoons. It was just published in July. The next day, Mankoff started his new role as Esquire’s humour and cartoon editor, inviting me to be a contributor. Back at the New Yorker, Emma Allen took over as cartoon editor with Colin Stokes as associate cartoon editor.

This story was published in Issue 89 (July 2017) of the Walkley Magazine. It first appeared on JasonChatfield.com.

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Jason Chatfield
The Walkley Magazine

New York-based Australian Comedian & Cartoonist for the New Yorker. Obsessed with productivity hacks, the creative process, and the Oxford comma.