Draw Me Anything with Jason Chatfield

Over Austin Kleon ’s shoulder, the whole time we talked, Lynda Barry watched us. Not the actual Lynda Barry; an original manuscript page from Cruddy , hanging on his studio wall next to an outtake from Making Comics . He calls them his Guardian Spirits, and the plan is to keep adding to them until he’s got a full pantheon of demigods looming over his desk. I understand the impulse completely. I’ve...

Let me tell you who Myq Kaplan is, because if you’re not already a fan, that changes today. He’s been doing comedy for going on twenty-five years. He has a Comedy Central special. He was a finalist on Last Comic Standing . He’s been on Comedy Bang Bang and Keith and the Girl more times than I can count. He has two specials on YouTube - AKA and Rini - and a new one he’s just recorded. He runs a Sub...

My drawing board is currently covered in a mix of art supplies and aggressively pungent deli meats. I’ve got a puddle of Higgins ink dangerously close to a towering pastrami on rye, and my entire apartment smells of mustard. Outside my window, a sanitation truck is violently reversing down 9th Avenue. The floorboards are vibrating. On my monitor, looking entirely too relaxed for a man navigating t...

There’s a cartoon early in Rich Sparks’s new book of a man my age, alone in a bath, lifting a spoon to his lips. No setup, no crowd, no scene. Just the act, and a title underneath: “Youp.” Where I’m from, that’s a diagnosis. My uncle Greg taught it to me as a child: “Mate, get a load of this bloke. He drinks his own fucken bath water.” (Australian for arrogant.) First cousin to tall poppy syndrome...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com When I first moved to New York 12 years ago, I did what every terrified transplant does: I asked other comedians for advice… This was a mistake, because comedians are a bag of cats and no two of them agree on anything. One told me to do every open mic in the city. One told me to do none of them. One told me, with...

“You cannot write a line of code that replaces the invisible labour, the thousands of terrible rough sketches, and the deeply human derangement required to make a truly great cartoon.” If you try to launch a print humor magazine in the 21st century, most financial advisors will tell you to just set your money on fire instead; it’s faster, it requires less paperwork, and it keeps you warmer in the...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com I am sitting at my drawing board in my sweltering Manhattan apartment. Grant is sitting in his room in Wichita, Kansas. The contrast between our two environments is immediate and palpable. His background is calm, lined with books. There is a quiet, steady, midwestern stillness to his frame that makes my own neuro...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com As always, if you want to watch the full replay, please upgrade to Paid. I really appreciate your support. If you want to test the absolute limits of your nervous system, try sitting in the middle of Times Square with a sketchbook, a pen, and an open microphone... It is a sensory assault. It does not smell like i...

When I first sat down to chat with Jeremy Caplan about artificial intelligence and digital productivity tools, I genuinely did not think we would end up talking about him playing the violin. I certainly did not expect the conversation to pivot into a deep, philosophical appreciation for the irreplaceable magic of humans sitting in a room together, simply enjoying a live performance. But tha’s the...

If you joined me last time I had the legendary Kevin “KAL” Kallaugher on the stream, you’ll remember we discussed the “Cartoonist’s Paradox” - the absurd reality where cartooning is incredibly easy to start, but absolutely impossible to stop once it gets its hooks into you. This time around, our conversation shifted gears. Instead of talking about how to get into the game, we talked about how to s...

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 w...

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...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com Episode Links: Book // Socials // Podcast // Website If you caught this chat live on Thursday, you know my chat with Sarah Elizabeth Hill didn’t bother with small talk. We dove straight into the deep end. Sarah writes, produces, and runs Bobi Media. She took $400 and built it into an agency that works with Oscar...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com 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....

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...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com 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 w...

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...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com \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 tim...

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… This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.ne...

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.com 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...

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...

Thank you Kevin KAL Kallaugher , Stan! , Paranormal Cartoons , Christopher Thornock , Cat Wilson RN , and the 600+ others who tuned into my live video with Ann Telnaes and Chappatte Cartoons ! Join me for my next live video in the app on Tuesday 24th @ 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 Watercolour Control Problem with Jessie Kanelos Weiner Earlier this year, I joined Jessie Kanelos Weiner —artist, author, and watercolour wizard—for a live chat about colour, chaos, and why watercolour refuses to obey. She just released Thinking in Watercolour , which made me realise I mostly think in panic, and snacks. This year, for 2026, she’s launching a series: 31 Days of Watercolor! whic...

Thank you Kevin KAL Kallaugher , asher , Margreet de Heer , Dan Collins , Pat Coakley , and many others for tuning into my live video with Tom Toro (and his cat, Pumpkin!) Tom is a New Yorker cartoonist, author, and the rare person who can make me feel simultaneously inspired and completely inadequate about my cartooning skills. His new book, And to Think We Started as a Book Club , just dropped,...

I went into this episode of DMA expecting the usual blend of cartooning shop talk and digital doodling. What I got was a deep dive into creative authenticity, delivered by someone who's figured out that being yourself is both the hardest and most obvious solution to every artistic problem. The Eugene Empire Asher's Hi It's Me Again had just dropped, and our conversation naturally gravitated toward...