Draw Me Anything with Jason Chatfield

About Draw Me Anything with Jason Chatfield

Live drawing videos with the most interesting creative minds in the world, hosted by Manhattan-based New Yorker cartoonist and comedian Jason Chatfield. www.newyorkcartoons.com (https://www.newyorkcartoons.com?utm_medium=podcast)

Publisher

Jason Chatfield

Category

arts · education

Language

en

Explicit

No

First episode

4 Jun 2025

Latest episode

13 Oct 2026

Latest episodes

43 episodes in the feed.

1. 

   13 Oct 2026

   You’re Not a Real Parent Until... (It’s Out Today!)

   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 (https://substack.com/profile/8316438-darlene-campbell), Rhonda, and TELMC (https://open.substack.com/pub/terri397203) 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 (http://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. (https://www.jasonchatfield.com/blog/cartoons-via-email-vs-social-media) 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? (https://www.newyorkcartoons.com/s/itsitpodcast), 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 (https://www.newyorkcartoons.com/subscribe?utm_medium=podcast&utm_campaign=CTA_2)

2. 

   10 Oct 2026

   DMA#59: Michael Maslin - Nearly 50 years at The New Yorker, AI-Generated Cartoons & King Kong drawn upside down

   This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com (https://www.newyorkcartoons.com?utm_medium=podcast&utm_campaign=CTA_7) 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 (https://substack.com/profile/8266872-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.

3. 

   9 Oct 2026

   DMA#59: with special guest Michael Maslin

   This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com (https://www.newyorkcartoons.com?utm_medium=podcast&utm_campaign=CTA_7) Stay tuned for the full recap tomorrow…

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