The sheer logistical terror of running a comedy festival is not something the average person truly understands.

You have to convince nearly a hundred highly neurotic, sleep-deprived stand-up comedians to travel to a single location. You have to make sure they get picked up at the airport. You have to house them. You have to pray they have the personal o…

I live in an ancient little apartment a block from Times Square, because I love cooking dinner in my bedroom.

It’s more of a ‘Pre-War Cupboard’ really. I ordered a mini fridge the other day because I needed a guest bedroom. Morris, my French bulldog, is asleep on a pile of discarded drawing paper, completely unbothered by the fact that his gourmet kibble requires legal tender. My radiator clangs with the aggressive rhythm of a stolen Citibike being dragged backwards down a flight of subway stairs.

It’s a very particular kind of anxiety. You want to make art, but you also want to occasionally eat a Chipotle burrito (strictly no beans). It’s an impossible Venn diagram. I’ve made my living for twenty-one years as a freelance artist and comedian. I don’t have a day job, I don’t have a side hustle, and I don’t have a wealthy patron bankrolling my Blackwing addiction.

Luckily, Mason Currey came on the show this week. He’s the author of Daily Rituals, a book I devoured during the pandemic, and his new hardcover is out right now. It’s called Making Art and Making a Living: Adventures in Funding a Creative Life.

When I first saw the title, I told Mason my immediate thought process. “I initially, when I got the book, thought it was finding a creative life,” I said. “And I was like, oh no, it’s way more important. Funding! It’s about money.”

We got into the weeds of how historical geniuses paid their bills, and honestly, it’s comforting to realise they were mostly just flailing around like the rest of us.

I started by asking about Arthur Schopenhauer, who managed to dodge a soul-crushing life in mercantile finance solely because his father died and left him an inheritance. I spend half my time wandering the concrete canyons of Manhattan, wondering how to pay my rent, so I had to ask Mason: Is the secret to artistic genius really just having a rich dad who dies at the exact right time?

“James Joyce, for instance, was an absolute nightmare of a human being…”

It turns out, the answer is a complicated ‘yes and no’. We discussed Charles Baudelaire, whose letters to his mother sounded violently familiar. I’ve always carried this quiet, crushing shame that I can’t just sit at a desk at 9:00am and produce brilliance. I struggle with regulating attention on demand and initiating tasks without a heroic amount of friction. When I can’t meet expectations, it feels intensely personal, like a reflection of who I am at my core.

I asked Mason if Baudelaire’s legendary financial chaos was a symptom of executive dysfunction. Mason pointed out that Baudelaire would let pressure build up until he was in a mad panic. “He talks about how he can’t make himself do the thing until it’s built up so much pressure that he finally does it in this explosion,” Mason said. “He sort of had run up so much debt that he’s forced to dodge creditors and continually be moving from place to place.”

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Leaving things until the absolute last second to manufacture adrenaline is a textbook symptom of ADHD. Baudelaire didn’t have the diagnostic criteria to explain his dopamine dysregulation, but he had the frantic, desperate energy of a man trying to outrun his own brain. He blew his inheritance, dodged his landlords, and begged his mother for loans just to buy firewood.

“The odd jobs that used to support young artists have basically evaporated… They’ve been swallowed up by algorithms and artificial intelligence.”

We talked about the absolute absurdity of how some artists survived their financial ruin. John Cage funded his avant-garde music by going on an Italian television quiz show as an amateur mushroom expert. (As one does). He won the modern equivalent of ninety grand and bought a Volkswagen van. I asked, "Are we all just one weird reality TV appearance away from funding our next creative project? Do I need to go on a baking programme and pretend I care about fondant just to afford fresh watercolour pans?” (I’m kidding. I did that already…)

Then there’s Fernando Pessoa, who inherited a hefty chunk of change. Did he invest it sensibly to live off the interest? Hell No! He blew the entire inheritance in less than a year, having an incredibly expensive printing press shipped from Spain to Portugal, of course…

We also spoke about the absurd methods we use to force ourselves into a productive headspace. For sixteen years, the only way I could get my daily newspaper comic strip done was a highly specific, slightly unhinged ritual. I told Mason all about Scotch Bath Sunday. I would get in the bathtub, pour myself a generous glass of peaty Scotch, and sit there with a yellow legal pad. No phones, no iPads, no laptops. Just me, the boiling water, and the looming terror of a deadline.

Mason loved it. “I think there is a little bit of superstition there,” he said, “but there’s also something really powerful about the repetition. You train your mind to get into that particular headspace on a somewhat regular basis.”

If there’s one thing I’ve been banging on about this week more than anything, it’s that finding a genuinely distinct visual voice in the modern cartooning landscape is brutal.

You need to be instantly recognisable. You need to be deeply funny. You need to build a world. (Oh, and try to make a living doing it.) Tom Chitty has built an entire universe. He is a British cartoonist based in Toronto, a regular contributor to the New Yorker, and an absolute master of the absurd and whimsical (okay, ‘silly’). His characters feature blocky bodies, wide stances, and an otherworldly charm. We sat down for Draw Me Anything yesterday to decode the mechanics of his highly specific, deeply funny brain.

Here is exactly how he builds his worlds…

The Serial Killer Sketchbook

Young artists obsess over perfect sketchbooks. They paint immaculate, highly composed spreads and post them online. It is a complete lie. Real sketchbooks look like the manifesto of a deranged serial killer. Look at the horrendous s**t I just found when I flicked open one of mine…

Tom learned this the hard way in animation school. A tutor looked at his work, told him to stop designing, and ordered him to just start generating ideas. he dropped the pressure of making a pretty picture. He started treating his drawings like handwriting. He now keeps a sketchbook on hand constantly, capturing raw, unfiltered nonsense. Six months later, he opens the book and finds completely forgotten, bizarre ideas that actually make him laugh.

You can’t force inspiration by sitting down and staring at a blank piece of paper. Taking a leaf out of every great artist’s book, he walks to the coffee shop every morning after dropping his son at school. Moving through the world and seeing the horizon literally dislodges ideas from the deep dark recesses of your skull.

The Regret of the “Send” Button

Pitching cartoons is an exercise in psychological torture. You curate a batch of ideas. You arrange them like you are sequencing a Radiohead album. (Yes, we’re exactly the same as Thom Yorke. Thank you.) You convince yourself the order matters. Then you hit send on the email.

The regret is immediate. You look at the batch two hours later and see nothing but glaring flaws. You wonder why you ever picked up a pen in the first place.

Tom survives this weekly cycle by treating it as a boot camp. He gets up, generates ideas, and commits to the sheer volume of the work. Early in his career, veteran cartoonists Matt Diffee and Bob Mankoff gave him ruthless, honest feedback. The ultimate lesson is simple: Do not draw what you think the New Yorker ‘wants’. Draw what makes you completely unique.

Ghost League Baseball and Wonky Parsnips

Tom is launching a Kickstarter on April 1st for an absolute masterpiece. It is called Nooks and Crannies of New York. It is compiled from the fictional chronicles of an eccentric explorer named Baron von Schoogenheimer.

The book is a staggering achievement in world-building. It took him three and a half years to draw. He documents Ghost League Baseball teams, including the Mysterios and their star pitcher Hodge Wang, famous for his penguin-wing throwing action. He documents subterranean trolls making furniture in the interborough tunnels. He draws Roof Mables, who live in disused water towers and help New Yorkers retrieve lost memories.

He grounds the absurdity by pulling from his own family history. He turns a childhood memory of eating Dutch Speculaas biscuits into an elaborate drawing of Schneek’s Belgian magic pedal-powered hot dog production cart.

He also understands the phonetic rhythm of comedy. Some words are just inherently funny. Tom used to run a website dedicated entirely to words with intrinsic humour value. Balloon. Spoon. Guff. Wonky parsnip. He injects this phonetic absurdity into every character name and fictional contraption he draws.

The Caboon and the Fly Ball

Halfway through the stream, we flipped the cameras and started scribbling. Tom uses a Staedtler 0.3 fineliner to achieve his incredibly detailed, controlled line work. After a suggestion from Hue Walker of a Frog on a Bat, he and I began drawing a Caboon, which is a feline-looking primate from his book that accompanies French Canadian taxi drivers to judge the character of potential passengers.

Meanwhile, the live chat was throwing out prompts. Paul Nesja suggested drawing the above-mentioned frog catching a fly ball. I sketched it out, immediately regretting my lack of reference material for amphibian anatomy. Drawing live while trying to conduct a coherent interview is basically an extreme sport, but it forces you to rely entirely on your muscle memory.

Wrestling with glitchy streaming software, fighting the algorithm, and writing these detailed process breakdowns requires a heady cocktail of caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Tom and me drawing live, please consider upgrading to a paid subscription for just $1 a week. It keeps the inkwell full, repays the massive labour, and keeps Morris supplied with the treats he demands.

We are actively fighting a deluge of generic, machine-generated content. You need to support live, human artists who spend years crafting weird, beautiful things. Go to Kickstarter on April 1st and search for Nooks and Crannies of New York. Back the project. Buy the book, and the folks at The American Bystander's Viral Load. Support the absolute necessity of being silly.

Now, if you will excuse me, I need to go burn my sketchbooks before the detectives arrive...

‘til next time!Your pal,

Jason

Tools and Resources We Yapped About Today:

Trying to succeed as a cartoonist is stupid. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. Emily Flake does both, and she makes it look infuriatingly easy.

My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.

The Alt-Weekly Education

Finding your voice requires failure. You need a low-stakes environment to make mistakes, draw weird things, and test boundaries. For Emily, that was the Baltimore City Paper.

She drew a strip called Lulu 8Ball for the alt-weekly. Alt-weeklies are dead now, which is a massive cultural tragedy. They gave artists absolute freedom. Emily figured out a four-beat joke structure, she honed her timing, and she cussed profusely. The traditional papers would never allow that. She is now bringing Lulu 8 Ball back to life on her brand-new Substack. Subscribe to it immediately please and thank you:

The Fraud Detector (Joke in a Box)

Writing jokes is a terrifying puzzle. I arrogantly assumed I knew exactly how to write one. Then I opened Emily’s physical card deck, Joke in a Box.

I read the exercises. I immediately realised I am a total fraud. The prompts are ruthless, practical, and highly effective. Fellow cartoonist Hillary Fitzgerald Campbell actually used the deck to write a joke and ended up selling a cartoon to the New Yorker. You can still buy this box of magic on Bookshop. Do not buy it on Amazon to fund a billionaire’s joyride.

St. Nell’s and the Ghost Hotel

Williamsport, Pennsylvania is a lumber town. It has haunted hotels and a bizarre vacuum of silence. It is also the home of St. Nell’s…

Emily bought a house out there during the pandemic after heading out there and staying in the haunted 100+ year-old hotel, The Genetti, as a little getaway to save her family from murdering each other in their sleep. Her husband told her they had absolutely no money for a second house, so she launched a Kickstarter and raised fifty grand. She turned the property into a free writer’s residency for women and marginalised genders. Three residents stay at a time for two weeks. They write, they sleep, and they create incredible work.

She even launched an entire comedy festival out there called Nellsfest. The town actually shows up and supports the artists. It is a brilliant community. (A lot of medical professionals, as it turns out.)

Longtime readers will remember our eventful booksigning event there earlier this year:

Hell Gigs and Toddler Jazz

Stand-up comedy is an exercise in public humiliation. We brought Hillary Fitzgerald Campbell onto the stream to discuss the absolute worst gigs we’ve ever survived (with emotional scars).

Hillary’s hell gig involved abruptly stopping a family jazz festival. The organisers forced three women to tell dirty jokes to a room full of toddlers. It is the textbook definition of a comedy nightmare.

Emily performed at a children’s play space in Stroudsburg. The audience consisted of exactly one woman sitting on a couch. The woman only spoke Spanish. She stood in a cavernous echo chamber, speaking English into a microphone taped to a stand with packing tape, essentially making bird noises.

My personal hell gig took place in a Williamsport bar. A massive basketball game played on the screens right next to the stage. The bartender connected her phone to the venue’s Bluetooth speakers. She forgot to turn off her keyboard sounds. I tried to tell jokes while the aggressive tap, tap, tap of her text messages blasted through the sound system… more below:

Boxing and Bombing

Getting punched in the face and bombing on stage are the exact same physical sensation.

Emily boxes. I box. Will Sylvince at the Comedy Cellar boxes. The overlap between comedians and fighters is massive. When you take a hit in the ring, it is not the pain that ruins you. It is the disorientation. You have to force your brain to stay in the game while you are completely compromised.

Comedy is identical. When a joke dies, the room turns hostile. You have to stay entirely in control while you are deeply uncomfortable. You eat dirt, you respect the hustle, and you get back up… I’ve written about this before:

Wrestling with glitchy streaming software, cutting through the digital noise, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Emily and Hillary drawing live, please consider upgrading to a paid subscription for just $1 a week.

Margreet is a brilliant Dutch comic artist and the former Comics Laureate of the Netherlands. She spent three years acting as an ambassador for the medium, literally compiling guides to help teachers get graphic novels onto high school reading lists. She is also someone who intimately understands the frantic reality of a creative life.

The Court Jesters & the Freedom Fighters

Margreet and I talked about the bizarre cultural divide in cartooning. In Australia, people generally look at comic artists like we are overgrown toddlers playing with crayons. It is treated as a silly little hobby. But if you take a train to France or Belgium, comic artists are treated like absolute rock gods.

I told her about a cartooning conference I went to in France called RIDEP. I was standing in a room with cartoonists from Tunisia, Sudan, and China. They had been exiled or forced into hiding for drawing anti-propaganda cartoons against dictatorial regimes. They were actual, literal freedom fighters. I draw jokes about talking dogs. I realised very quickly that I am more of a court jester. It was a profoundly humbling reality check.

Making a living as an artist requires you to constantly ask people for money, which is something most cartoonists are fundamentally terrible at doing. Margreet is an expert in crowdfunding, having run multiple successful campaigns in Holland to bypass the traditional publishing gatekeepers.

The Kickstarter Scam…

But she recently got targeted by a very clever, highly sophisticated Kickstarter scam. Scammers will pledge a massive amount of money to your campaign just to get your attention. Then, they send a highly convincing email from a “notification bot,” claiming your account is suspended, and your money is frozen. They provide a link to steal your credentials. Margreet described it as the digital equivalent of being lured away from a busy high street into a dark alley. We are already sweating over our drawing boards; we do not need thieves making it harder.

Related viewing:

My interview with the Founders of Zoop:

Theology and Annoying Mrs Lee

Margreet has a fascinating background. She originally flunked out of school because she hated the technology, so she pivoted to studying theology at the University of Amsterdam. Both of her parents are ministers, so it was in her blood. While she was there, she drew a comic for the faculty paper called The Adventures of Jesus. (Which sounds like the working title for The Bible).

I completely related to her fascination with religion as a storytelling mechanism. I went to an Anglican high school, and I used to infuriate my Bible study teacher, Mrs Lee. I would sit in the back, drawing cartoons and interrogating the text with the obnoxious persistence of a discount detective. I just wanted to know how the plot holes were resolved. Mrs Lee did not appreciate my feedback. She hated me.

The 3:00 AM Eyeball Hack

The absolute most valuable thing I took away from our chat was a neurological trick for my broken, sleep-deprived brain. We were talking about meditation and dealing with anxiety, and Margreet told me about an EMDR-style hack she uses when she is trapped in a rumination loop.

If you want to read about my annoying high school Bible study questions, a completely bizarre neurological hack to cure insomnia, and the absolute hazard of using a dip pen in bed, consider upgrading to a paid subscription for just $1 a week. It keeps the ink flowing & Morris fed.

Thank you Andi Penner, chris eliopoulos, Bear Edwards, Ann Feild, PJ Pierce, and many others for tuning into my live video with Alex Hallatt! Join me for my next live video in the app.

Some notable quotes from this week’s episode:

* “We can’t just be blinkered and think, ‘Oh my God, as creatives, this is an existential threat, and we have to stop it, because we’re not stopping it. It’s like the internet, but bigger.”

* “You can continue doing what you’re doing, the way you’re doing it, but you better be bloody good because you’re going to become an artisan.”

* “You don’t pay the plumber for banging on the pipes, you pay him for knowing where to bang.”

* “Cartoonists die at the drawing board.”

* “AI is coming like the printing press came for monks and illuminated manuscripts. Do you think the monks were pissed off or do you think they were relieved?”

Today’s Draw Me Anything featured the return of the brilliant Alex Hallatt, creator of the syndicated strip Arctic Circle and the Substack Cartooning in the Age of AI.

Alex joined us from Dorset, UK, where the weather is currently “not very lovely,” which is British for “apocalyptic.”

We dove straight into the giant robotic goblin in the room: Artificial Intelligence. Alex approaches this topic with a “scientist brain” (she used to work in clinical research), which makes her perspective refreshingly pragmatic. Instead of just panicking, she’s looking at how to survive. She compared the current AI panic to the early days of digital photography, when old-school photographers insisted it wasn’t “real” photography. Now, shooting on film is an “artisan” pursuit. The lesson? If we want to keep drawing by hand, we’d better be bloody good at it, because we are all becoming artisans now.

One of the funniest moments came when Alex described how she uses AI to handle the “tedious” stuff, like finding the secret service menu on her storage heaters, so she didn’t have to pay an engineer £200 to push three buttons. It’s the “plumber analogy”: you’re not paying for the button pressing; you’re paying for knowing which button to press. And right now, AI knows where the buttons are.

We also talked about the “enshittification” of platforms like Amazon, where search results are now buried under AI-generated guidebooks and sponsored slop. It’s getting harder for independent creators to be found, which is why building a direct relationship with readers (like on Substack) is the only real lifeboat. As Alex put it, “I want to have a chat... human connection has real value in an AI world.”

\While I was going back and re-listening to this episode to write the recap below, I wrote down so many gems that she shared- tips I will honestly keep with me forever. This was a really great conversation. I hope you find it as valuable as I did.

I am currently setting a new personal record for the number of times I can wash the same load of laundry without ever putting it in the dryer.

I think I’m on wash number five. I put the clothes in, turn the machine on, walk away, immediately forget the machine exists, and then remember three days later when the super tells me the basement has started smelling like a wet golden retriever that has been trapped in a swamp. So, I wash them again. And the cycle continues.

This is what having an adult ADHD brain actually looks like. It’s not just being a little “flighty” or getting distracted by shiny objects. It’s a relentless, exhausting daily battle with your own executive function. It’s opening an email, deciding you don’t have the emotional bandwidth to answer it, marking it as “unread,” snoozing it to tomorrow, and then doing that exact same sequence of events 49 more times over a two-week period.

This is also why my chat with Jenny Lawson on yesterday’s Draw Me Anything was less of an interview and more of an aggressively validating group therapy session.

Jenny Lawson (thebloggess) has been writing online for over 15 years, and she has a new book coming out on March 31st called How to Be Okay When Nothing Is Okay: Tips and Tricks That Kept Me Alive, Happy, and Creative in Spite of Myself.

I got an advance copy, and I genuinely could not put it down. Have you ever read a book so good you run out of sticky notes?

It is a wildly funny, deeply vulnerable survival guide for anyone whose brain is a slightly hostile work environment. Jenny and I both share a potent daily cocktail of ADHD, anxiety, and an inability to perceive the passage of time. (I currently have nine clocks in my apartment, and I am still late to everything I have ever attended.) Here are a few of the brilliant, sanity-saving things we talked about during the stream, including why you should always strive to be a Murder Potato.

2. Humour As a Means of Defanging Hard Things

Jenny and I both use comedy as a coping mechanism. We talked about how, when terrible things happen, humour is the only way to genuinely process the grief.

“I think humour is super helpful for me,” Jenny said. “If I can laugh at something, instead of this enormous monster, it becomes like a little bit smaller, a little bit easier to understand.”

It’s an on-ramp. If you write about crushing depression, anxiety, or mental illness, people who don’t suffer from those things might immediately put the book down. But if you make them laugh, it invites them in. It tells them that the stakes aren’t going to crush them.

“If you make somebody laugh, first of all, you invite them in, and you say, ‘It’s okay. It’s not that serious, even when it’s serious,” Jenny explained. “A lot of people who have either reached out to me and said, ‘I read this because it was funny. And then later, years later, when I found myself in depression for the first time... I could go back and be like, oh, okay, I’m not alone.’”

2. Rejection Sensitivity & Farting at the Queen

If you have ADHD, you likely suffer from Rejection Sensitive Dysphoria (RSD). This means you spend a terrifying amount of your day convincing yourself that everyone secretly hates you.

“I constantly am sure that I have said something wrong, done something wrong. I overthink, I second-guess,” Jenny confessed. “The amount of work that I do in my head... it is exhausting.”

You leave a conversation, and ten seconds later, you are meticulously replaying every word, convinced you offended someone. You assume if a friend hasn’t texted back in four hours, they have legally disowned you. You live in a constant state of wondering, “Are we fighting? Are you mad at me?”

Jenny’s friend gave her some advice that completely short-circuits this panic. She asked Jenny to try to remember the last time she saw someone else completely mortify themselves in public.

Jenny couldn’t think of a single time.

“She was like, ‘No, what it really is, is everyone is constantly doing it. But you’re only paying attention to yourself,” Jenny told me. “Nobody is paying attention to how I fed something up because they’re way more worried about the thing that they fed up.”

This led us to my absolute favourite chapter in Jenny’s entire book, brilliantly titled: But Did You Fart at a Queen?

It turns out, there is a historical account from the 1600s of the 17th Earl of Oxford. He was bowing to Queen Elizabeth, and while doing so, he let out a massive, echoing fart. He was so intensely mortified by this bodily betrayal that he literally imposed a seven-year exile on himself. He left the country for seven years. When he finally returned, the Queen greeted him and said, “My Lord, I had forgotten the fart.”

She didn’t even remember. She had a country to run; she wasn’t thinking about his flatulence.

So, the next time you lie awake at 3:00 AM sweating over a slightly awkward joke you made to a barista, just ask yourself: Did I fart at a Queen? No? Then I’m doing fine.

3. The Spoon Theory (and Budgeting Your Sanity)

Trying to explain executive dysfunction to a neurotypical person is like trying to explain calculus to a golden retriever. They just tilt their head and look at you blankly. “Why don’t you just do the thing?” they ask.

If you want to hear about the Spoon Theory (and how to explain your exhaustion to a neurotypical person), Shirley Jackson’s brilliant method for handling internet trolls, and why you should aspire to be a Murder Potato, upgrade your subscription below. It costs less than a bodega coffee, and it ensures I can eventually afford a dryer that actually works.

I spent an hour yesterday talking to Elijah Woolery and Aarron Walter from the Design Better podcast, and by “talking,” I mean I went on several extended, caffeinated tangents about the existential dread of artificial intelligence, my masochistic love for 19th-century stati…

Thank you Beth Spencer, asher Perlman, Alex Hallatt, Margreet de Heer, chris eliopoulos, and many others for tuning into my live video and asking questions of my guest Kyle Beaudette! Join me for my next live video in the app.

I have a confession to make. I keep a secret folder on my computer. It’s not what you think, but it is deeply weird. It’s just labelled “Kyle,” and it is filled with screenshots of drawings by the Canadian artist Kyle Beaudette.

Whenever I’m feeling uninspired, creatively blocked, or just generally annoyed by the blank page, I open the Kyle folder. It is full of wobbly lines, strange creatures, and a frankly alarming amount of beautifully rendered bodily fluids.

Yesterday, I finally got to open the folder and talk to the man himself on Draw Me Anything. Kyle joined me from the frozen expanses of Canada (a fellow Commonwealth resident) for a conversation about the creative process, the horror of social media and AI Art, and how a tin of brown watercolour paint accidentally ruined his life.

Kyle is one of those infuriatingly talented people who didn’t even go to art school. He studied theater, and then spent a decade teaching himself how to sculpt by hanging out on an internet forum run by two brothers from Texas. For years, he was making these incredibly intricate, Tim Burton-esque sculptures. But the pivot to drawing happened in the most unexpected place: a middle school classroom.

As a substitute teacher, Kyle realised he needed a way to connect with the kids fast so he wouldn’t just be “the weird man that they don’t respect”. So, he sat down with a black pen and started drawing with them. He made a rule for himself: no pencils. He would only draw in pen, force himself to make mistakes, and then force himself to live with them. It was an exercise in embracing the mess, and it completely forged the “consistently wobbly” style he has today.

He achieves this signature wobble, by the way, by holding a tiny 01 Micron pen completely straight up and down while shaking his hand slightly. It’s a technique that his teachers tried to train out of him, which is exactly why it works so well.

But my absolute favourite story from the stream was the origin of his most popular subject matter: poop. A few years ago, Kyle’s mother bought him a beautiful Daniel Smith watercolour tin for Christmas. He opened it up and was horrified to find it was a landscape palette, absolutely loaded with different shades of brown. Thinking he had no use for them, he jokingly decided to use the browns to paint a gross picture of a turkey pooping.

People loved it. He did it again. Before he knew it, he was the internet’s premier artist of gastrointestinal distress. He also shared a pro-tip for the aspiring scatological artists out there: if you use Quinacridone Burnt Orange, it scans with a reddish tint, leading concerned followers to constantly advise him to see a gastroenterologist. This is the kind of high-level artistic insight you simply cannot get at RISD.

We also talked about the heartbreaking reality of having your brilliant, original ideas crushed by history. Kyle recently published a gorgeous book called The Garden Witch. Initially, he planned to build 50 sets and photograph his sculptures for it, like a lost stop-motion film. When that turned out to be a logistical nightmare, he asked the publisher if he could just do it in watercolour and ink instead. They said yes, and asked if he knew how to paint with watercolours. He lied, said yes, and immediately started frantically Googling videos of Quentin Blake.

He wanted to combine Blake’s loose, scratchy line work with the sheer narrative insanity of William Steig. He poured his heart and soul into the project. Then, a month before he finished, he discovered that Quentin Blake and William Steig had actually collaborated on a book together years ago. It’s called Wizzil, and it’s about a witch who looks exactly like his character, right down to the frizzy hair. He said he completely “died inside,” which is the only appropriate reaction to finding out two legends already casually dashed off your magnum opus decades ago.

While we talked, we drew. I whipped up an “amoeba unicorn” that slowly morphed into a bat because I accidentally gave it a pig nose. We also fielded a request from the chat to draw a pigeon getting chased by one of Kyle’s creatures, which naturally ended with the pigeon pooping itself.

Hi friends,

This conversation is so important for people to hear, so I’ve decided to remove the paywall on the replay. Please feel free to share it with anyone you think might find it useful to hear.

Your pal,

Jason

---

Join me for my next live video in the app on Wednesday 25th @ 12pm when I speak with fellow New Yorker cartoonist and author, Liza Donnelly.

But first, the recap…

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to.”

That was the line that stuck with me after yesterday’s Draw Me Anything. It was spoken by Patrick Chappatte (Chappatte Cartoons), one of the most respected editorial cartoonists in the world, and it perfectly encapsulates the strange, suffocating atmosphere of 2026.

I was joined by Patrick (who joined us from Geneva) and the legendary US-based cartoonist Ann Telnaes for a 45-minute conversation that was less of an artist chat and more like a war room briefing. We had over 600 people tune in live (a record for this show!), which tells me that I am not the only one feeling the need to huddle together for warmth around the glow of a screen.

If you missed it, above is the full replay (for paid subscribers) and a breakdown of what we discussed. And we discussed a lot.

My Guests

If you are new here, let me briefly introduce the titans I was sharing a screen with:

* Ann Telnaes is a two-time Pulitzer Prize-winning editorial cartoonist. She was a staff cartoonist at The Washington Post until early last year, when she resigned after a cartoon was spiked- a canary in the coal mine for the media landscape we now find ourselves in. She now publishes independently on Substack, where her work remains as sharp, elegant, and devastating as ever. (She also revealed a little secret during the stream: she is still using an old-school metal animation disc from the 1980s to create her work!)

* Patrick Chappatte is a globetrotting cartoonist whose work has appeared in The New York Times, Le Canard Enchaîné, Der Spiegel, and countless others. He is also the Chair of the Freedom Cartoonists Foundation in Geneva. He has a unique talent for “comics journalism” -reportage drawn on the ground- including a recent interactive piece for Le Temps about the surreal spectacle of Donald Trump taking Davos “hostage”.

The Conversation: “Obeying in Advance”

We spent a lot of time talking about their upcoming book, Censorship (or Self-Censorship) in America. The book has already been published in French and is coming out in German, but (tellingly) they are still in negotiations for a U.S. publisher.

Why? Because, as Patrick noted, American publishers seem terrified of inviting the wrath of the administration.

This led us to the core theme of the chat: “Obeying in Advance.”

As Patrick explained:

“In an autocracy, the autocrat never picks up the phone. He doesn’t have to... It’s the people in charge, the editors, the publishers, the media owners, all those guys doing the job in advance. You don’t need censorship anymore. Because self-censorship will do the job for you.”

We discussed the recent incident involving Stephen Colbert and Texas Representative James Talarico, where a segment was reportedly suppressed—a classic example of corporate cowardice disguised as editorial discretion. Anne pointed out that this isn’t just about media control; it’s about the administration’s fear of losing its religious base. Talarico, a devout Christian who believes in the separation of church and state, represents a threat to the monolithic narrative Trump relies on.

The “Gábor Pápai” Warning

Patrick shared a chilling story about Gábor Pápai, a Hungarian cartoonist who won the Courage in Cartooning Award. Papay warned them years ago:

“If you guys in the United States or in Europe get to elect the populists... you’re going to follow the same path that we are following.”

Papay has been sued by his government and called a “cockroach” on national television. Patrick noted that while every country is different, the pattern—using the legal system to harass critics, demonising the press, and slowly eroding norms—is universal.

The U.S. has now fallen to #57 on the press freedom index, sandwiched between Sierra Leone and Gambia. As Patrick put it: “I’m not hopeful that the U.S. is going to go up in this context in the foreseeable future.”

The Immigrant Experience

One of the most moving parts of the conversation was when we touched on our shared status as immigrants. I am an Australian-American; Anne is Norwegian-American; Patrick is Swiss-Lebanese with an American son born in New York…

We talked about the dehumanising rhetoric being used against immigrants- the “animals,” the detention centres, the “denaturalisation” task force that is now reportedly targeting naturalised citizens.

Anne was visibly angry:

“I cannot tell you how angry this makes me... I’m a naturalized citizen just like you... He is definitely running on fear. That’s how he got into office in the first place.”

Patrick added a heartbreaking observation about how the world now views America:

“It’s a broken love. That’s the feeling in the rest of the world. Because there was so much goodwill toward the United States and its values. And the cruelty... it’s really sad.”

Why You Need to Follow Them

We ended on a note of solidarity. We are all feeling the squeeze—whether it’s the algorithms, the publishers, or just the general atmosphere of dread. But as Anne and Patrick proved, the only way through it is to keep drawing, keep publishing, and keep supporting each other.

Please, go subscribe to their Substacks. They are doing the work that the legacy media is too afraid to do.

* Ann Telnaes on Substack

* Patrick Chappatte on Substack

And thank you to everyone who tuned in. It felt important.

You can buy their new book here or in the U.S. at these bookstores:

Lectures de France Inc (Chicago)Foreign Book Source (Chicago)Bonjour Books (Kensington)French Books OnlineFrench & European Publications (New York)Librairie Albertine - Alliance Française of New York|Pierre International Bookstore (Tamarac)World of Reading (Atlanta)

‘til next timeYour pal,

Related Viewing:

* DMA#25: Ann Telnaes on the Power of the Pen (and Why She Left The Post) – My conversation with Ann from last year, before the election, which now feels like a lifetime ago: