How Bob Eckstein Outdrew Me With a Stick Dipped in Ink

There are two kinds of cartoonists in the world. The first kind look like they live in a studio. The second kind look like they live for their studio. Bob Eckstein, as it turns out, somehow lives inside both.

When Bob logged into Draw Me Anything, he was already mid-anecdote about being thrown onstage at a conference with Leslie Stahl, Ann Patchett and a sudden last-minute change that left him alone in front of hundreds of people. “I had no moderator,” he said, “so I just talked for half an hour about Trump being elected the night before.” The punchline was that the famous authors who followed him bombed. Already the lesson was clear: There is justice in comedy. Occasionally.

Bob has taught writing at NYU and writes a newsletter I love called

The Bob

. So naturally, I asked him why he is so good at talking about the craft of writing without drifting into the kind of mystical babble that makes young writers want to take up dentistry. His answer was simple: People overwrite. They step on their own jokes. They forget to read the room. “Accessible beats clever,” he said. “If your writing is too flowery, you lose the audience.”

We drifted into the evolution of comedy and how everyone now thinks they are the funniest person in their friend group. Bob calls it American confidence. I explained that in Australia, we are raised to never think too highly of ourselves. If you get too confident, the national sport is to cut you down like a tall poppy and inform you that you are drinking your own bathwater. Bob laughed and said, “So that is what you all say about us behind our backs.” (I mean… He’s not wrong.)

One of my favourite stories was how late Bob came to cartooning. The late, great, Sam Gross invited him to the New Yorker cartoonist lunch, told him to come back with a batch of drawings, and somehow the very first cartoon Bob submitted sold. Not normal. Not fair. Deeply annoying. But also, inspiring.

He talked about the passing of Sam and how it marked the end of a certain era of camaraderie in cartooning. Now everyone is scattered, hustling, trying to keep the lights on.

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Bob showed us his studios. Plural. His outdoor office is literally a ten-dollar Adirondack bench he bolted to the roof so he can write in the breeze like a ship’s captain awaiting orders. His indoor studio looks like the set of Master and Commander, built by someone avoiding deadlines.

At one point, entirely unprompted, Bob pulled out a drawing he made with a stick dipped in ink. He then revealed a portrait he drew of me in ten seconds. Meanwhile, I had been quietly sweating while trying to draw Adam and Eve at a restaurant table with a snake waiter. Bob made it look like breathing.

We talked about productivity, and he shared a tip from a hyper-productive artist friend who whispered the secret to a prolific career: