How To Write and Sell A Cartoon to The New Yorker

Dear Friend,

Sammi and I recently sold our fiftieth New Yorker cartoon. I typed that sentence and then went back to make sure it could be true, because it feels like it has to not be true. But in fact, the number is somehow closer to 60, which I am telling you, I guess, just to brag about it.

I’ve had a hard time writing this post. First, because (as mentioned already) it feels braggy. Second, because I usually write the cartoons in partnership with my dear friend Sammi, and I would never force her to co-write a piece about co-writing cartoons. (Though, I did just text her to ask her if she wanted to add anything, so we’ll see if she texts back.) (Note: she texted back something too falsely flattering for me to repeat here in good conscience.) Third, I have the type of imposter syndrome (SORRY) where it’s like, “If I write about this, someone is going to pop out of the woodwork and tell me that I actually don’t know what the hell I’m doing.” But it’s been six years (and eight since we started submitting), and while I might not know everything about how to do this, I know exactly how I do it. And every time an artist writes something like this, I want to read it. It’s good to see people’s paths.

I remember clearly two important events that led to the beginning of this story.

The first one was that I was in the bath tub and it was winter break. (As an aside, I literally cannot remember the last time I took a bath, and that’s wild, because I used to take one pretty much every day. I wish I could still take a bath, but having a child seems to have obliterated the option. I used to lie in the bath and dream about the life I wanted; now I live the life I wanted and dream about lying in the bath.) I was devouring a Puzzles and Cartoons issue of The New Yorker. New Yorker cartoons, I thought, were kind of the perfect art form. Each cartoon had to do a lot with a little. They involved words and art. And at their best, they managed to be incredibly funny. For as long as I can remember, I’ve cared a lot about things being funny.

In the bath, I decided that I would pour some energy into getting a square-shaped New Yorker cartoon published in the magazine. At this point, I’d had a few Daily Shouts run online, so I had the cartoon editor’s email address. And – this is always true – you don’t succeed when you don’t try.

But when I sat down to try, I failed. I couldn’t think of even one cartoon, let alone the ten you’re supposed to pitch in a batch. A few weeks later, my friend Sammi, who was not yet a writer at The Onion, but was already the funniest person I knew, invited me to have drinks with her at a whiskey bar in Lakeview. (Or I invited her, or it was mutual. Sorry; whiskey was involved.) She pitched the idea that maybe we write together – she was interested in screenwriting a pilot or something. And here’s a thing that I think about a lot: I don’t know that anyone before had asked me to collaborate with them in this way. Like, people had asked (and continue to ask) if I wanted to illustrate their children’s books for them (no), but it’s rare that someone comes to you and is like, “I genuinely like the work you make and I want to make work with you.” It feels really good! And it felt really fun.

I was enthusiastic, and I also had these cartoons on the brain, so I brought up the idea of writing some single-panel gags together. My friend Sophie (no relation) often did New Yorker cartoons with her friend, so I knew it was a possibility, and Sammi was so funny. I just felt like she’d be good at it.

This was pre-pandemic, so at first we wrote cartoons together in person. We met up at The Office of Modern Composition1, which has an extraordinary view of Lake Michigan, and tried, independently, to write jokes. I cannot overstate this: we were both so bad at it. I remember, for example, sitting across from Sammi and being like, “OK, I have the caption for one, but not the picture. It’s like, something about sweater weather.” And then Sammi was like, “Yeah, that’s good.” You’re not missing anything, reader. That was all I had. AND WE THOUGHT IT WAS GOOD.

I’m going to try to dig up early brainstorming pages from those sessions, because I know I saved them and they are somewhere in my office. My memory is that we spent such a long time on those brainstorms, and they were just awful. We picked five of mine and five of hers, and I agreed to draw them. I thought it would be easy to draw black-and-white cartoons, but actually, working in grayscale is an art, and drawing in a visually cohesive and funny way is an even greater art. The drawings took me hours, and they were terrible. I sent them to Sammi and she was like, “THESE ARE GREAT!” This is an important thing for a collaborator to be able to do: to tell you the thing you made that sucks is great. You have to hear that you’re doing a great job from someone, just in order to keep going.

I sent in the ten cartoons, and of course, all ten were rejected. Here, though, we experienced some incredible luck. Emma, the cartoon editor, wrote us back! Emma does not have to write people back. She has a lot of people submitting cartoons to her. Here is what she said in that email, in case you ever send a batch and don’t get an email back – you can imagine you got this one. I think we were in the right place at the right time, and that’s why we got this.

So glad to have you submitting gags! Sadly, none made the cut this week (I get 1,000, show David 60, and buy 20, so don’t ever take it too personally). But I think these are really promising. I loved the Tamagotchi and crystals jokes and of course the drawings are excellent (especially Cats and birthday party). Only note is no need to draw a line between art and caption. Fine to just have it sit below. And I think best to avoid flat gray washes for backgrounds—they muddy things up a bit.

Hope that’s helpful and that you send more soon.

It was helpful, and unnecessary, and we were very thankful. We met back in person, repeated the process, and sent in another ten bad cartoons. She said they were “much better!” There’s an email exchange between me and Sammi where we are like, “WOW.” Ultimately, we submitted thirteen batches of ten – that’s 130 total cartoons – that were rejected.

The pandemic came, and now Sammi and I could not meet in person anymore. We moved to Zoom, which actually meant we could meet more often, since we weren’t having to get all the way downtown to write jokes. We replicated the process, except that we spent a little longer gossiping, and then we turned cameras off and went into our own caves for an hour each, and then got back together to read over joke lists. We typed the jokes into a Google Doc, and they were (and to this day continue to be) mostly bad. I know I am becoming a broken record with this “we were bad at this” stuff, but I think it’s important to know how much bad stuff many people have to wade through to get to anything remotely good.

AND – a new paragraph for this – an advantage to writing with a partner is that you can read each and every bad joke to her, without worrying that you’re going to end up wasting time drawing something that isn’t good. Sometimes she sees something brilliant in a joke I thought was stupid, and vice versa. Sometimes she’ll be like, “What if it was a hermit crab instead of a lobster?” and the whole joke is instantly ten times better. It’s great to have someone to sort through the raw material with. It’s also great to have someone to share your joke about Pinocchio going down on a lady who likes the way his long wooden nose feels and tells him to tell her more lies. That’s not going to be a cartoon — this is the New Yorker, people, have some class— but damn if it isn’t incredibly fucking funny to me.

So we had a rhythm, and we’d gotten used to rejection. We’d made an Instagram account for our rejects, and I loved seeing Sammi on a regular basis. Things were basically good.

And then, on April 4, 2020, right at the start of the first year of the pandemic, we got an email whose subject line was, “O.K.”

It felt like it must be a mistake, but I emailed to check, and it wasn’t.

What happened next:

1. Sammi and I exchanged EMAILS THAT WERE WRITTEN IN ALL CAPS AND WERE RIDDLED WITH TYPOS.

2. I mixed a gin and tonic. This is not a thing I ever did; I don’t even own gin or tonic. I had roommates who did. I put a lime in it.

3. I went up on the roof and thought about my enemy. I have one enemy. He doesn’t have to be my enemy, but he chose that path, and that is fine. It’s fine to have an enemy. I thought, “My enemy will see that this has happened, and he will be jealous. I’m so happy about it.”

4. I wished I had had a different reaction and felt like I was a bad person, because shouldn’t I just be purely happy about this? A life dream? ACTUALIZED? But oh well. You don’t get to pick your reactions to things, and at this stage of my life, I cared so much about making my enemy feel jealous.

   1. Now that I have a child, I could not care less. In fact, I wish my enemy well. More happy people is better. I hope he succeeds and gets all the things he wants. I want to stress that meditation, therapy, yoga, and an understanding of Buddhist philosophy did nothing to help me arrive at this mindset. All along, it just required that I be a type of bone-tired I did not know it was possible to be. There is simply no energy to hate an enemy anymore.

5. Several weeks passed, and eventually, our cartoon was printed in a real magazine, beneath an article about Boris Johnson. I walked to the newsstand near my house (I have no idea how this place is surviving, tbh, but it’s the best place on Earth), and bought four copies of the magazine. I told the guy behind the counter – it’s always that guy behind the counter there – that I was in the magazine. He was nonplussed. I sailed home on a cloud.

I think I imagined that we would submit another 100 cartoons and then finally sell another one maybe, but actually, once we’d broken through, it became much easier to sell the cartoons. We sold a cartoon about chickens in the next batch. And then we were selling cartoons like it was our job. Because it was our job!

It slightly, slightly irritates me that people think that I do not write the jokes because I do draw the pictures. I write half of the jokes, and Sammi writes the other half of the jokes. Both of our jokes are chosen, and way more of both of our jokes are rejected. I have, in fact, submitted some solo batches when Sammi’s been traveling, or whatever. But I don’t like doing the solo batches. I like every part of the ritual of meeting with Sammi: writing the jokes; reading the good and the bad out loud to her; hearing her say, “Yeah that’s funny,” even when something is not funny; and laughing until I pee at the jokes that she writes.

It’s amazing to look back and realize that we’ve been doing this for eight human years. I grew a person in my body and she’s become a Self since then. She is not interested in my job, but I do tell her, apropos of nothing, that I am a cartoonist. That’s what I wanted to be when I loafed in the 2018 bathtub with a magazine and a dream, and now that’s what I am. In fact, we got an “O.K.” at the exact minute that my daughter was born. (I found out later. I was busy.)

When that one came out, I took a picture of my tiny new person next to the cartoon in print and sent the picture to Emma.

Six years after our first “O.K.,” I still feel the same thrill run through my blood when I get another one. When I’m feeling sad (I have never admitted this to anyone before), I do a search in my Gmail for “Emma Allen O.K.,” and then just stare at the stack of “O.K.”s in my Inbox. It feels like when your crush texts you, BUT BETTER AND MORE. I let my stomach flip until I feel better, settled into this reality where somehow, I am doing what I wanted to do.

There are lessons here, and they feel worthwhile to share. One is that this is a thing that I do when I’m not doing my full-time job, or parenting. If I did not think this was the most fun thing to do in the whole world (I do think that), then it would not be worth the time it takes. Because it is… a lot of time. Another lesson is that persistence matters. I think we are drawn to stories where things happen fast, but nothing in my life has happened fast. Everything takes a long time, and the only way to arrive is to keep going.

And here’s something you might not have expected: I think Sammi is at a disadvantage because writing for The Onion uses a completely different part of your humor-writing brain than writing New Yorker cartoons. I know this, because I auditioned to write for The Onion a few years ago and was like, “Oh my god, I can’t do both these things. It’s like walking down a path into a deep forest, and then walking a mile back to venture into a totally different forest that’s in the absolute opposite direction.” That’s the only way I can describe it. The fact that she can humor-code-switch so easily ought to be vehemently applauded — and the same goes for anyone who writes more than one type of funny thing.

My process for writing New Yorker jokes now, which is something I am less bad at than I used to be, is:

1. Look at a boatload of New Yorker cartoons other people have written. Laugh and think about how I will never be as funny as those other people, but I will valiantly try to emulate them.

2. Think, “OK, what do I notice I’ve heard people saying a lot? And who would be the funniest possible person to say that thing in a cartoon?”

   1. For example, early in the pandemic, I wanted to write a cartoon where someone was saying, “Not everything is unprecedented.” It was at a time where people had stopped saying “unprecedented,” and had started complaining about people saying “unprecedented.” Here’s what I came up with. I still feel proud of this one:

   

3. Then, when that doesn’t work, think, “What is a thing a bird would say that a person might also say?” I write a ton of bird jokes. It does not always work.

4. Look around the place I’m sitting and notice objects and think, “What’s something people sometimes say about [item]? And who would be the funniest possible person to say that thing in a cartoon?”

5. Text Sammi that I need ten more minutes, because who can write ten jokes in an hour? It’s always too ambitious.

6. Think, “OK, but how hard will this be to draw?”

Joke-writing is the most searching-for-the-muse-like writing I have experienced. It’s like sitting very still near a place you know an owl lives. If you are still and quiet enough, the owl will come to you. The joke is the owl. Don’t poke any nests, or you will fail.

Re: drawing the cartoons. I thought it would start to take me less time to draw, but in general, drawing or painting anything has started taking me a longer time the more I learn. This is also true about cooking, right? You realize there are ways to make the food good, and then you don’t want to cut any corners. My drawing has gotten better. But there have been funny jokes we’ve written that suffered because I couldn’t possibly draw it. New Yorker cartoons, like anything else, are their own language, and you slowly learn to speak it. It’s fun to learn a language!

Sometimes I want to read about someone’s craft, and some of you have expressed interest in that too. Nevertheless, at the heart of this is something human: I wanted to tell jokes, but for reasons I won’t go into here, the stage wasn’t the place for me. Now I’m in brilliant company, doing something that some of the greatest humorists of all time also did. This was a way in; a door. I try to tell my students that there are always other ways in. I tell them, too, that the world wants to hear their voices, even if they don’t care about everything they have to say. And once in a while, even though everything is garbage, it’s worth reflecting on the fact that we are a species that is able to make, and to laugh, and to try new things on for our entire lives, and that’s actually kind of really special.

Good luck out there, bravely facing all that breaks your heart.

Love,

Sophie

• Lol, Sammi and I have a New Yorker cartoon in the issue of The New Yorker that came out two weeks ago!

  

• I think probably lots of New Yorker cartoonists have written a version of this essay but better — but I never miss Liana Finck’s newsletter, and Jason Chatfield has my favorite newsletter for cartooning craft.

• Less than three hours from now, I’ll be at the Gerber-Hart library to discuss “Kin: The Future of Family.”

  

• Thank you for all the seriously kind words about the library bench! I have to go through and respond to comments, but I see all of them, and feel them in my heart.

• We are in the middle of a heatwave. I like it, and I am sorry.

• I know this is the wrong thing to feel about it.

• I am sitting in a non-air conditioned room sweating with the fan on my face.

• But ants are crawling on me, too, which I guess I shouldn’t blame on the heat, but I do. You forget how often ants come. They come and then they’re here. They have no boundaries. They are very smart.

• Can we talk for a minute about jumpsuits / rompers? I love them as an ITEM, but I CANNOT STAND THE WORK I MUST DO TO PEE. The one that Kat got me from Big Bud Press (used, and I still think it cost $900) is great because it has a simple zipper on the front. That’s not too much. But the one I rented that I’m wearing now has TWO TYPES OF BUTTONS. Why? I am sitting here with it mostly just unbuttoned because I am going to have to pee soon. Actually, I have to pee now! But I’ve got to get this newsletter out, it’s ridiculous how long this one has taken me.

• What do you guys feel about all the talk about protein these days?