Draw Me Anything with Jason Chatfield

Michael Maslin has been in The New Yorker for 49 years…He has catalogued every cartoonist who ever drew for the magazine, and wanted me to know that, off camera, he is surrounded by “a lot more books.” (Not his books. Just books. A man after my own heart.)Thank you to everyone who tuned in and left comments during our live stream— a reminder: the live streams are, and will always be, free. If you missed it live, the replay is above. And the recap is written out below. Here’s what happened, (with the links down the bottom…)(This takes me a long while... so I paywall this part. I hope you understand.)First, a correction to my own promo post (oops). I told you the magazine didn’t let him draw his first sale. Wrong. He did draw it. It went in with a regular batch, Lee Lorenz saw the drawing, and then came the note: “We’re just taking the idea.” Whitney Darrow Jr. would draw it instead…“You want your foot in the door, but this wasn’t the foot in the door. This is a toe.”He didn’t even tell his friends. Too confusing to explain. These days, people get a credit line beside the artist; back then it was “kind of hush-hush.”The cartoon, you’ll remember, was a fortune teller telling a man, “Nothing will ever happen to you.” Decades later, Bob Mankoff asked if Michael still had his own drawing of it, and ran it online. “So it got its day in the sun.”His first cartoon under his own name, in April 1978, was a man at a deli counter: “I’ll have a quarter pound of your most reliable cheese.” It would not have been his pick. (Same, Michael. They never take the one you’d pick. Mine was “Vlad The Employer ffs) But he said, “I was extremely glad, of course… that my life changed.”Michael told me he submitted for something like six or seven years before anything sold. His very first batch was drawings with no captions at all, nothing to do with cartoons, sent in because a friend told him to. It came back with the standard rejection slip, and someone at the magazine had pencilled a note along the bottom: next time, send an SASE.He didn’t know what an SASE was. He was a kid. “But the next time you send in is what I focused on.”They haven’t stopped hearing from him since. They created a monster.He moved to New York for one reason: to get into The New Yorker. He was sending 50 or 60 ideas a week on index cards. (He still has the index cards. Of course he does. He’s Michael friggin’ Maslin.) After many, many… many months of nothing, he got a phone appointment with Lee Lorenz and asked what he was doing wrong.“You’re just not right for the magazine.”End of discussion. He thanked Lee for his time and hung up. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.comJessie Kanelos Weiner came back on Draw Me Anything this morning. That makes her my only three-time guest, which I announced live and then immediately wondered aloud whether we still had anything to talk about. (We did. We talked for 45 minutes and I never once got to the drawing I’d prepared.)(Watch the full replay above.)Jessie is an illustrator, an author, a Substacker and a stand-up comedian, and she does all of it from Paris, where she has lived for 18 years. She writes La Vie en Watercolor, she wrote the book Thinking in Watercolor, she runs painting retreats, she teaches at an art school, and she has a kid who fences.The UN of audiences…Last month, in Paris, Jessie very kindly got me a spot at Coucou Comedy, one of the English-speaking clubs over there. We got coffee the morning of the show and I was, by my own admission, terrified. Not of the audience. Of the faux pas. I don’t know the minutiae of a Paris room.Jessie says the thing that unites that room is wanting to hear someone talk badly about the French. The great unifier.She also says Paris audiences are more generous than American ones. She performed in the States for the first time last year and found you really have to beg people for their attention. In Paris, a lot of them have never seen live stand-up before and don’t know what the rules are. There are no rules yet. There is, however, a strong influence from French clown culture, which has apparently produced a number of what she called disenfranchised clowns who have found their way to stand-up.I pointed out that that is just what comedians are.Lean into the fun…Jessie was going through her mum’s old papers and found a Christmas letter from when she was four or five. The recap of her year was: Jessie likes to cut up things and paste them together.

Hello again, friend!We did it. Scott Dooley and I birthed a book!You’re Not a Real Parent Until... is out today. It’s pub day! (Publication day, for those of you not in the biz. For those of you in the biz, my condolences.)Earlier today, Scott and I went live here on Substack for our official virtual launch. Thank you to everyone who tuned in live and shared your parenting experiences! (Watch the full replay above.)First, the winners... We promised to give away one free copy of the book. Then, mid-show, without checking with Scott, I gave away two more.Congratulations to: Darlene Campbell, Rhonda, and TELMC If that’s you, reply to this email with your postal address (or a PO box, whatever you’re comfortable sharing with two strange men who draw children wearing underwear on their heads), and we’ll get your copy in the mail.Everyone else: you can buy it right now at yourenotareal.com!The experiment.Normally, when you put a book out, you do press. Podcasts, TV, radio, guest articles, reviews. We’ve done none of that.Instead, we’re trying to sell this book using only Substack. No ad spend, no publicist, no begging an algorithm for mercy.This isn’t a “help me become a New York Times bestseller” thing. (Those are GoFundMes with extra steps.) It’s that we’ve talked to a lot of friends with books out, some with huge publishers, some self-publishing, some with a million followers, and none of them has found a marketing method that reliably works. Worse, the second they post a link to something they’re selling, the platforms quietly bury it.Substack is different. You opted in. You signed up to hear from me about the things I make. So we’re going to see whether a couple of lower-to-middle-rung cartoon-makers can sell a book by talking directly to the humans who actually want to hear from them, and showing you how we made it.We’ll document all of it here, so if you’ve got a book (or anything else) to sell, you’ll see what works and what doesn’t. (We should point out that we have not cleared this with our publishers. This experiment may be career-limiting.)The book follows parents from babies to toddlers to tweens to teens to “all grown up”. Every page is a gag that starts with You’re not a real parent until... and a cartoon underneath.We pump three or four hundred punchlines into a spreadsheet, all with the same setup. Then we hash them out over a series of meetings at bars around Manhattan: the wording, the image, which ones live. (One of the rods for our backs: not starting every single punchline with the word “you”.)Every drawing was done by hand. Pencil, dip pen and ink, then colour. For the first time in my life I used a colourist, the brilliant Nahia Mouhica, and I’ll never go back. We printed it on matte paper so it feels like an art book rather than something you’d find in a dentist’s waiting room.Scott is a parent. His son Leo is two, and the book is dedicated to him. (Technically, Scott says, it was for Messi. He was going through a whole Barcelona thing.) I am not a parent. So we built out families. Divorcees, same-sex couples, mixed-race couples, widows and widowers, all with names and kids of their own, so the gags could run as stories across the book. There’s even a death in the middle. Scott is the guy who dies. (Why not?)Our favourite image in the book is from that storyline:A couple of gags got gentle pushback from the publisher. One was, in the technical language of the industry, “a bit nipply”. Another was “This too shall pass”, which has been said in reference to something a child has swallowed. That one made it in. (You’re welcome.)The whole point of the book, underneath the poo jokes, is that there’s no single right way to do this. Everyone’s figuring it out as they go, and you don’t have to be perfect. As Scott pointed out, the people most outspoken about bad parenting usually don’t have children. It’s like being told how to stack your dishwasher by someone who doesn’t own a dishwasher. (I would like to reiterate: I am not a parent.)From the chat...We asked you to finish the sentence You’re not a real parent until... and you delivered:Rhonda (three kids, two grandkids): ...you’re perfectly fine with your three-year-old’s fashion choice of undies on her head, as long as it keeps her ears warm.This sent us down a rabbit hole about leg holes. Y-fronts leave the ears out. Boxer briefs offer full coverage. And somewhere in there, a cartoon was born: two kids with underpants on their heads, one of them in Calvin Kleins. (Rich Dad, Poor Dad.)Darlene has three daughters and now three grandchildren, which puts her firmly in the book’s “all grown up” section: the parents whose children come to them for advice and then completely ignore it.Another viewer shared that becoming a parent cut the time it takes to get dressed in the morning from an hour to 10 minutes. Which, as Scott pointed out, puts parents on par with pop stars doing backstage costume changes.And Tracy asked me to draw a bee. So I drew a bee. It was, by general consensus, a B minus.What’s next?We’re going to do more of these lives, and we’ll announce them in advance. (Tracy, you asked. Done.) If you’ve got a Substack and want us to come on and chat, reply and tell us. We’ll document that too.I’ll also be writing more here about how the series started, how a premise becomes a book, and what happens to this experiment. (and all the behind-the-scenes drawing stuff you know I love yapping about.)And if you can’t wait, Scott and I do a podcast about coming up with cartoon ideas, Is There Something In This?, where you can watch us do the same thing every week with less paper.Please buy the book!The single best thing you can do for this experiment is buy a copy today, ideally two. One for you, one for the parent in your life who has stepped on a Lego in the dark and said nothing.And if this experiment doesn’t work, we’ll document that too. (Career-limiting, remember?)‘til next time!Your pal,PS. 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

Thursday, midday. Paul Noth is in Milwaukee, where he moved back after 20 years split between the Upper East Side and the Princeton area, and where he now has, as he put it while wandering to another room mid-stream to chase better WiFi, multiple rooms. (We get it, Paul. You don’t live in Manhattan anymore.)First order of business: it’s Noth, rhymes with both. He’s been letting people say “Nawth” for decades out of Midwestern politeness. Gosh. Consider yourselves corrected on his behalf. If you missed it live, the replay is above. Here’s what happened, with every link we promised on air down the bottom…Pre-orderers get a signed bookplate posted to them! Just shoot him an email at [email protected] with your mailing address and your desired inscription. (A proof-of-purchase screenshot is also much appreciated.)You know Paul’s most famous cartoon even if you don’t know his name: the flock of sheep gazing up at a billboard of a wolf, captioned “He tells it like it is.” It’s among the most shared cartoons in the magazine’s history; it’s now the cover of his book, and Paul has mixed feelings about its immortality. “It should be a historical document by now,. he said, a little wearily. Here’s the detail that should be laminated and handed to every rejected cartoonist on earth: The New Yorker rejected it the first time he submitted it. So did they reject his other most popular cartoons, first time ‘round. Paul resubmits. He always has, fortified by a story he’d heard about Saul Steinberg, who supposedly used to take his rejected cartoons, put them straight into a fresh envelope, and post them back to the magazine. (The balls on this guy! I love him.)Paul sold to The New Yorker in 2004. The cartoon: a White House press secretary holding a torch under his chin like a kid telling a ghost story, while a reporter asks how he responds to critics who say he’s just trying to scare people. He’d worked on that batch for the best part of 2 months under the wing of Matt Diffee, whom he’d met at the Rejection Show and who walked the batch in to Bob Mankoff.At Paul’s first look meeting, surrounded by his heroes (Gahan Wilson among them), Mankoff greeted the new arrival with two sentences that became his entire art education. The first: “Don’t get cocky.” The second: “I want to see 10 a week from you, even if they’re s**t.” Paul has done 10 a week ever since, through every all-nighter, every TV job, every book. “It was my art school in a lot of ways,” he said. Like me, he’d never been to one. He’d never had art in public before. He learned to draw in public, 10 at a time, and eventually stripped away his early etching-style hatch marks when he realised the truth every gag cartoonist arrives at eventually: “The best style for me was the best execution of the joke.” Or as Lee Lorenz put it in The Art of the New Yorker, which we both worship: a cartoon is beautiful the way a sailboat is beautiful. It has exactly what it needs to function, and nothing else.Mankoff gave me my version of that lecture too, around 2014, back when I wore a suit jacket to the offices like I was auditioning for a bank. He looked at my batch of borrowed styles and asked what I think about when I do my hair in the morning. “Try and think about your drawings as your hairdo. It’s a style you’ve arrived at. You’re not trying to copy Johnny Depp.” This from a man with famously luxurious amounts of hair. It worked, though. It worked on both of us.The Pale Force story is even better than I’d hoped. Jim Gaffigan, it turns out, is Paul’s brother-in-law; he’d married Paul’s sister a year or two before. Paul, not yet a New Yorker cartoonist, pitched Jim an animated bit for Late Night with Conan O’Brien, modelled on Steve Martin turning up to Letterman with something weird in his back pocket. When the head writer asked whether he’d done animation before, Paul said yes. (He had made flip books, so… technically not a lie?)The budget was roughly what a guest gets paid for sitting on the couch, which is not a number that produces animation, and his first delivery came back with the note that a 16-megabyte video file cannot be broadcast on network television. The night the first episode aired, running on no sleep, he watched it freeze for a single millisecond and briefly died. Then it killed, the series got Emmy-nominated, and Paul got a comedy education by osmosis: Robert Smigel, Brian Stack and Demetri Martin down the hall, Conan’s face providing the biggest laugh of every episode no matter what Paul animated. His conclusion, having vowed never to do low-budget animation again: Worth it.The Laureate Report…I put the important questions to Wisconsin’s inaugural Cartoonist Laureate, and I can now report the following to the people. There is no salary. There is no diplomatic immunity. There is, crucially, no sash: “I have to make the sash myself, apparently. Like a Mayor McCheese-style sash.” His opening list of demands included full access to the Oscar Mayer Wienermobile. His actual duties, in his own words: “to figure out what the hell the cartoonist laureate does.” So far that means cartoon classes for kids, library outreach, trying to attach a cash prize for whoever comes next (”that’s what cartoonists actually need let’s be real”), and a retrospective of 175 of his originals opening at the Museum of Wisconsin Art in January, sharing a title with the book. When the museum’s president first floated the laureateship, Paul assumed she meant Lynda Barry, P.S. Mueller or Craig Thompson. She meant him.His process, for the process junkies: 10 ideas written first thing every morning, “usually bad”, purely to switch on the part of the brain that notices things. Voice memos through the day, transcribed the next morning. And this, which made my week: Paul had listened to Tuesday’s episode with Brian Biggs and co-signed the boredom sermon. “If I keep the stimulus away, I just keep things mentally kind of quiet; I will start entertaining myself after a while.” Three episodes ago this was my crank theory. It is now, I’m declaring, the official position of the show.Somewhere in here Matt Diffee himself materialised in the chat, speak of the devil, and was informed we’d been blaming everything wrong in Paul’s life on him. For the record: Diffee ushered in a whole generation of cartoonists, Paul among them, and his Rejection Collection books are the sacred texts of everything above.Paul’s dad was a lifelong newspaper man who brought home cartoon collections from the feature desk for his cartoon-obsessed kid, and who gave him one piece of career advice: don’t go into print media. He could see the writing on the wall. So Paul didn’t pursue it. He tried screenplays, plays, other lives. “I look back at an old notebook where I was trying to write a screenplay,” he said, “and the margins are just full of cartoons. In retrospect, it should have been obvious.”At the end, Paul described what this show apparently is: “It’s basically like a digital cartoonist lunch.” The magazine’s cartoonists used to eat together every Tuesday. We don’t anymore. I suppose I’ve been rebuilding the table an hour at a time, and I couldn’t be happier about who keeps sitting down at it.Now, the promised links…Pre-order I Am Going to Eat You... and Other Awkward Truths Out 13 October, 200+ of his most-loved cartoons plus 50 never published, and Paul says the unpublished ones “are usually the funniest ones, to be honest”. Pre-orderers get a signed bookplate posted to them! Just shoot him an email at [email protected] with your mailing address and your desired inscription. (A proof-of-purchase screenshot is also much appreciated.)Pre-orders are everything in publishing now, so if you were going to buy it anyway, buying it today is the whole ballgame. And since our books share a birthday: pre-order You’re Not a Real Paren… This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

Wednesday, midday… Brian Biggs is alone in his Philadelphia studio, an old garage he describes as a hermit cave, holding his phone in one hand and a pen in the other. I’m at my drawing board doing the same. For the next hour, 90 people watched 2 grown men show each other their doodles.If you missed it live, the replay is above. What follows is what you missed, with links to everything we held up to the camera.Brian has made more than 80 books. The Everything Goes series, Tinyville Town, the New York Times-bestselling Frank Einstein books with Jon Scieszka. So naturally, when he started his Substack, the imposter syndrome turned up anyway. “I had to give myself a break,” he said, “and get past my oh-no ego and just let it happen.”“All I want to do, man, is just draw. I just want to draw. When I was a kid, I got in trouble for drawing and telling stories… and I have to remember that I’m 58 and that’s what I do every day now.The turn came on an exercise bike in his basement, listening to Giuseppe Castellano’s podcast episode with myself and Adam Ming, where Adam Ming said to stop treating Substack as the road to being published and start treating it as being published. “It just was one of those ding moments,” Brian said. He got off the bike and got to work.The work is The Walk, and the story behind it is every author’s recurring nightmare. In 2019, Brian published a picture book with Penguin called The Space Walk: an astronaut, alone in space, who just wants to go outside. It came out, in his words, “to the great yawn of indifference of children’s publishing”, and was out of print within a couple of years.But out of print means the rights come home. So Brian is now turning that orphaned story into a full graphic novel, and serialising every step of it on his Substack: thumbnails, wrong turns, existential wobbles, all of it. “Every stupid thought I’m having about this is going onto my Substack,” he said. The story is already mutinying. “The story has decided it wants to be something bigger than I think I want it to be,” he told me, having informed his wife that morning it might be three 200-page volumes. “I’m 58 years old, man. Do I have a 600-page graphic novel in front of me?”The logic, though, is sound: last time, the book arrived to silence. This time, “at least it’s going to be a thing that there’s an audience built in already following it. And they care about it.” Every page will be hand-lettered, incidentally, because Brian letters the way you’d read it aloud, and he’d rather do that than make a font. He’s seen his hand-lettering redrawn by translators into Hebrew and Chinese, stroke by stroke. “I would love to meet those people one day,” he said, “but I’m afraid they would punch me in the face.”Somewhere in the middle of all this I made him explain the line in his bio about being calligrapher to a princess, and I’m pleased to report it’s all true. Junior year at Parsons, 1988, studying in Paris, he answered a job-board ad to address envelopes for a man in a cravat who threw parties for people like the Rothschilds. Which is how a kid from Texas, whose calligraphy career began with a drugstore Speedball set and the Renaissance Fairs of early-80s Houston, ended up hand-lettering the guest book for Princess Ghislaine de Polignac, whose family had been friends with Marie Antoinette, and who hosted Ronald and Nancy Reagan a few weeks later. Brian was escorted out as the Reagans arrived. He did the work at his apartment drawing table, Enya on the stereo (not sure which album…), his roommate’s Akira comics all over the futon.A year or 2 later, he was waiting tables at a Bennigan’s, telling anyone who’d listen: “I was a calligrapher for a princess for a month.”S**t Brushes and Other Filing SystemsThen I flipped the camera, and we got into the pens, as is my tradition. Highlights of the show-and-tell: his Kuretake brush pens, my Hunt 101, the ink bottle I suction-cup to train tables, and his filing system of labelled coffee cans reading “new brushes”, “good brushes” and (after asking the stream’s permission to swear) “s**t brushes”. He keeps a box labelled “used but might be useful on a rainy day”. He made it in 1994. It’s bloody full. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.comOn Wednesday at 8pm, I did something I have never done in 20 years of cartooning: I drew a stork, live, on the internet, while two grown men discussed laundry detergent… (I know. Weird that it took me so long, right?!)Let me back up.I went live on Substack with my co-authors on a book we’re writing about how couples can run a home without slowly startin…

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.comCarly Valancy beamed in from Valencia, Spain.Some of you will remember Carly. She interviewed me on her Substack, A Good Omen, a while back. This week I got to return fire.Four years ago, Carly reached out to the writer Alex Dobrenko`. When she interviewed him, she asked who she should talk to next. He said me. She sent me one email. I said yes. Then I sent her one email (”I know how busy you are, but...”), and she said yes. Somewhere since then, I also filled out the intake form for her next Reach Out Party cohort, which means I am now both her interviewer and her student, a conflict of interest I intend to exploit fully.She told me my ask landed as a gift, not an imposition: “I ran outside and told my husband. You know what’s so cool? The chain of events that can happen from one email or DM.” That’s her entire body of work in a sentence. One email. Everything else is scaffolding.Carly is a former actor. Broadway community, Hell’s Kitchen, 44th Street, the whole catastrophe. At about 25, stuck in a coffee shop job she hated and hunting for an agent, she did the thing that would become her life’s work without knowing it: she reached out to 1 stranger a day for 100 days.It worked, in the boring, verifiable way these things sometimes do. She found an agent she’s still friends with. She booked a national tour. And around day 82, she finally mentioned the whole scheme to her acting coach, who was appalled. Not by the project. By the secrecy. “You have to tell people you’re doing this!” Then: “When you get to day 100, you should throw a party at the studio. I’ll host it. You can call it Carly Valancy’s Reach Out Party.”She ran the 100 days again at 30, and the second lap taught her the lesson hiding inside the first:“There was so much more beauty in the process, in who I became in it and how I found my voice. A lot of people treat networking as a means to an end. It’s something you do when you need something. Instead, think about it as a process of becoming.”Carly has a phrase I’ve been carrying around like a lucky coin: increasing your surface area for luck. More reach-outs, more rooms, more chances for the universe to trip over you. Lately she’s refined it into something even better: “placing yourself in the current of serendipity”…I asked her to define a good omen, given she’s named an entire publication after one. She gave me a visual instead:“I’m going to give you a lava lamp. It’s constantly moving, and there’s some kind of glow about it where you’re just like, what is that thing? It’s got texture, and it’s alive.”Then she gave me a better one, borrowed from the theatre director Anne Bogart, whom she cold-emailed (of course she did) with the same question:

Subscribe, rate, and please leave us a funny ⭐️⭐️⭐️⭐️⭐️ review wherever you listen to podcasts.Welcome back for another episode of Is There Something In This? Outside, seaplanes kept coming down the East River like they’d been thrown, and every twenty minutes Scott and I stopped mid-sentence to watch one not crash. One aborted, came around, and hit the water hard enough that we both made the noise. Nobody plans these segments. I’m back from Columbus, where actual listeners turned up and forced us to describe our audience out loud. Here’s what we landed on: you’re pretentious, but you’re dumb enough to know you shouldn’t be. You want Barry Blitt on trade deficits, but you also want to know if the mouse has a really big dick. You are, in other words, exactly like us. (btw here’s a thing: I’m now live-drawing the ideas as we go, so the video version on Substack and YouTube is where you can watch me ruin a perfectly good joke in real time.)Then we did the jokes. A jester’s head in the guillotine bucket, and the salesman who pitched the guillotine to the king as a workflow disruption. A MoMA guard with a new sign about muttering AI slop near the Van Gogh. A snowman in couples counselling, his wife a bucket of water: “I just think this summer has changed her.” A moth has an idea, and every moth for miles descends on it…Somewhere in there, we stopped writing jokes and got onto the Flock cameras, the licence-plate network that lets cops look up their exes without a subpoena.Also: the balls on the Big Merino, a pigeon with a hustle, a Borg water tower in Greenpoint, and a Gallagher courtroom gag from which Scott has formally removed his name. Because why not?Our new book, You’re Not a Real Parent Until..., is out on October 13th and available for pre-order now wherever you buy books. It has, I’m reliably informed, already reached one bookshelf in Moscow.By the way, if you want to binge all of our previous episodes in an endless playlist like it’s some kind of Netflix Drama that just got nominated for an Emmy®, you can find our entire backlog right here.Send us your cartoon idea suggestions! We can’t guarantee we will read every one on the show, but we will read all messages we get here.Subscribe now▶ Be sure to send in your suggestions via Instagram @newyorkcartoons or [email protected]. Cheers!▶ Buy our new book at: www.realdogowner.com▶ Check out our Facebook page at: www.facebook.com/ITSITpodcast‘til next time!Your pal,PS. 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.Copyright Disclaimers: We’re inviting you into our living room; don’t walk out with our lamp. Please refrain from selling our jokes. All original content is © Copyright 2024 Jason Chatfield & Scott Dooley for “Is There Something In This?” All rights reserved.We welcome you to download and play the podcast and share it with others for personal use; please acknowledge “Is There Something in This?” Podcast as the source of the material. You may not, except with our express written permission, distribute or commercially exploit the content.On the topic: This podcast may include images that are used under the Fair Use doctrine of the U.S. Copyright Act (17 U.S.C. § 107). These images are utilised for purposes such as commentary, criticism, news reporting, education, and research. Fair Use allows for the limited use of copyrighted material without requiring permission from the rights holder, provided the use does not infringe upon the market value of the original work.We do not claim ownership of any third-party images used in this podcast. All rights remain with their respective copyright holders. If you believe your copyrighted work has been used in a way that does not fall within Fair Use, please contact us, and we will address any concerns promptly. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

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 Tom Toro , our official ‘Ryan Seacrest of Comic-Con’ gossip elbowed his way in to the streamTom 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.”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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.newyorkcartoons.com/subscribe

I said at the top of this episode that I didn’t want to call Josh Gondelman a comedian, because the word does about a third of the required work.Here is the CV, and I have since checked it against his actual bio rather than my memory, which is a courtesy I extend to guests and to no one else. Five years at Last Week Tonight with John Oliver, first as web producer and then as staff writer, where he collected four Emmy Awards, two Peabody Awards and three WGA Awards. Head writer and executive producer on Desus & Mero at Showtime. A contributor to the final season of The Marvelous Mrs. Maisel. Two stand-up specials: People Pleaser (2022) and Positive Reinforcement (2025). A book of essays, Nice Try: Stories of Best Intentions and Mixed Results. Co-creator of the parody Twitter account @SeinfeldToday. A regular panellist on NPR’s Wait Wait... Don’t Tell Me!We first met about ten years ago at Union Hall, doing Picture This, the show where cartoonists draw live while comedians perform and everyone pretends this is a normal way to spend an evening. I have two deeply unemployable skills: cartoonist and comedian. My parents are thrilled. Picture This is the only place on earth where both of them are load-bearing at once.Josh’s read on it was better than mine:“You’re watching something that’s never happened before and will never happen again. Everybody is kind of on edge seeing how the artists will interpret the comedy and how the comedians will react to the art. It’s perfect.”We also remembered a show where the comic on stage was working a long stretch about diarrhoea, and I, being a professional, had no choice but to render it. Gratuitously. Backstage was a convivial disgrace. We were crying.That’s the whole show, really. Backstage is better than the stage. (Don’t tell the box office.)The Overnight Success That Took 9 YearsI confessed that I had followed @SeinfeldToday for years without ever once registering that Josh was behind it. He co-created it with Jack Moore in late 2012: log lines for Seinfeld episodes, were they to exist in the present day, and present day was 2012 into 2013… which is now a period piece.The numbers are f*****g absurd:“By, I would say, 48 hours later, it had like 100,000 followers... Never had anything like that happen to me before or since. It was like as close as I had to being Hawk Tuah.”The Sunday night the account was formed, Josh had dinner with a friend who worked as a manager. She told him, gently, that she loved working with him and would keep helping him out, but that her boss was after clients with a slightly higher profile.Two days later, the boss wanted a meeting. And to sign him!“I’ve never seen something turn on a dime like that in my life before.”He had samples. He’d been doing stand-up for years. But he didn’t have the bulletproof script sitting in a drawer waiting for the world to finally notice him. He had drafts that were “all kind of a little rough.” So the lightning struck, and he spent the next year converting it into late-night writing applications, one at a time, like a man turning a lottery win into a mortgage.The heat arrives whether or not you’re ready. It doesn’t wait while you tidy up.The Taste of a 57-Year-Old Father of ThreeNice Try is a collection of essays, and I have described it, to Josh’s face and now to you, as being like “A Kind David Sedaris.” He took the compliment the way he takes everything, which is to say he immediately turned it into an admission of ongoing inadequacy:“We moved into a new apartment last week and I was just shelving my books and I saw my old copies of Naked... I haven’t looked at it in years, but it was like, I’m chasing that still as a prose writer.”Same. The personal essay has a king, and we are both loitering outside the palace.There’s a bit in the book about a childhood library trip and discovering R.L. Stine, and a line about having the taste of a 57-year-old father of three.“Books were kind of the place where I could have more adult taste. My parents were a little more protective with movies and TV and even violent video games. But with books, it was kind of whatever I could get my hands on.”Which is how a child ends up with real, considered positions on prime John Grisham. The Rainmaker. The Client. The Firm. He said “prime Grisham” the way other men say “prime Coltrane.” That truly is 57-year-old-father-of-three behaviour.Writing in Someone Else’s MouthHere’s the thing about Josh’s writing that I’ve never been able to get past. Him on stage is him on the page. The voice is identical, and it’s completely unique, and yet he spent five years writing in an acerbic British one, and got four Emmys for it.How?Below: how you make an atrocity funny without becoming a ghoul, the word Gary Gulman put in my head that I can’t get out, the pumpkin quiche incident, and why the meanest guy in the room in 2007 was never the one to copy.“In a good writer’s room, the best writer’s rooms, I think, have real diversity of perspective. And so even when the host is filtering it through how they think and talk and see things, you are bringing what your interests and ideas are when you can get it through the lens of what they do.”Part of what the host wants, he said, is breadth. He pointed to a Last Week Tonight piece made after his time there, on Black hair care and health, led by Ali Barthwell:“That’s really cool that John has the range to go, I’m going to figure out how to talk about this thing that is compelling to me even though it is not of my personal experience. And then I want someone like Ali who can go, I can speak to this from personal experience and I can make it sound right coming out of John.”So it isn’t impressionism. It’s not doing the accent in your head. You learn the show’s keystone phrases and structures and referential touchstones, and then:“How can I expand this palette in directions, like in vectors, that are fun and specific to me as well?”Which means that all those weird esoteric tangents, the ones that feel like they’ve been beamed in from a stranger’s dream? Those are somebody’s fingerprints, and if you know the room, you can dust for them.“Oh, this is about an angry penguin with a whimsical name. And you’re like, well, that’s a Jill Twiss specialty for sure.”He also recalled an extremely elaborate bit, requiring numerous graphic mock-ups, concerning an ornate sex party at Wes Anderson’s house. Unmistakably Will Tracy, who went on to write The Menu and Bugonia and worked on Succession for its entire run.Now that I think about it, I’d always been able to spot Asher Perlman on Colbert the same way. There’s a full stop that arrives, and you go: ah. There he is.Getting Your Fingernails UnderneathI asked him the question I actually wanted answered. At Last Week Tonight, he had to take genuinely bleak news and other material and make it funny. Not funny instead of serious. Funny as the delivery mechanism for serious.“I think that layer kind of lets you take a couple of harder swings.”You don’t always mock the tragedy. You mock the discourse around the tragedy. But, he said, it doesn’t always have to be removed levels of commentary. Sometimes the material walks right up and hands you itself:“Then you see the CEO of the company that did the polluting going, look, you gotta dump sludge somewhere. And you’re like, okay, that we can make fun of. We can make fun of this a*****e.”Then the second part, which is the best description of comedy writing I’ve heard in a long time:“Look for the little things where you can get your fingernails underneath and go, oh, I can claw something up here that’s fun and funny, and not just a wry good point.”Because a very good point that only elicits ‘clapter’ is, as he put it, its own thing. Fine. Applause is not laughter and laughter is not agreement.“There’s an idea that you can really sink into someone’s subconscious, that they walk away and they’re actually thinking about it going, holy s**t.”…“The efforts of these shows are not mostly to change the … This is a public episode. 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