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PODCAST

Draw Me Anything with Jason Chatfield

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

arts visual arts

All Episodes

4:38

DMA#38: India Ink, Insomnia, and Internet Thieves...

Draw Me Anything with Jason Chatfield ·

2026/03/13

This is a free preview of a paid episode. To hear more, visit www.newyorkcartoons.comMargreet 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 FightersMargreet and I talked about the bizarre

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32:38

DMA#37: How to Survive Farting At The Queen (and Why...

Draw Me Anything with Jason Chatfield ·

2026/03/09

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 times I can wash the same load of laundry without ever putting it in the dryer.I think I’m on wash number

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59:38

The AI Uncanny Valley, the Hunt 101 Nib, and What...

Draw Me Anything with Jason Chatfield ·

2026/02/28

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.newyorkcartoons.com/subscribe

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30:57

DMA#37: How to Draw Diarrhea and Influence People (A...

Draw Me Anything with Jason Chatfield ·

2026/02/27

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

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46:06

🔓 Unlocked: DMA#35: Drawing on the Edge of the...

Draw Me Anything with Jason Chatfield ·

2026/02/23

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

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46:06

DMA#35: Drawing on the Edge of the Authoritarian...

Draw Me Anything with Jason Chatfield ·

2026/02/18

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 phone. He doesn’t have to.”That was the line that stuck with me after yesterday’s Draw Me Anything. It was

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5:06

DMA#34: Cartooning for the Apocalypse (and...

Draw Me Anything with Jason Chatfield ·

2026/02/10

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

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33:55

The Watercolour Control Problem with Jessie Kanelos...

Draw Me Anything with Jason Chatfield ·

2025/10/10

The Watercolour Control Problem with Jessie Kanelos WeinerThis week, 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 ink, panic, and snacks.Jessie asked how I approach colour, and I admitted that I approach it sparingly. I used to think “real artists” painted every shadow like da Vinci. Then I saw the da Vincis at the Met

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58:01

The Art of Drawing Worse with Tom Toro

Draw Me Anything with Jason Chatfield ·

2025/10/08

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, and it’s already Andy Borowitz’s October Book Club pick. The title itself is a gag from one of his

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56:30

Asher Perlman & The Art of Eugene

Draw Me Anything with Jason Chatfield ·

2025/10/06

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 EmpireAsher's Hi It's Me Again had just dropped, and our conversation naturally gravitated towards his most famous creation: Eugene. For the uninitiated, Eugene is that wide-eyed, innocent character who

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60:00

Liza Donnelly on Breaking Barriers, Drawing Aliens,...

Draw Me Anything with Jason Chatfield ·

2025/09/27

Thank you Stan!, E. Sjule, Margreet de Heer, Loitt, Michael Maslin's Ink Spill, and the nearly 500 others for tuning into my live video with Liza Donnelly yesterday! Join me for my next live video in the app next Thursday, Sept 4th at 12pm EST when I speak with political cartoonist Kevin KAL Kallaugher. You can follow his new Substack here:Nearly 500 people tuned in yesterday for Drawing Me Anything #25, and honestly, I'm not sure if they came for the cartoons or just to watch me fumble with my

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61:45

Adventure Sketching, Pickleball, & Bus Rides with...

Draw Me Anything with Jason Chatfield ·

2025/07/01

I spent an hour yesterday drawing with Samantha Dion Baker —artist, author, and one the best Substackers on drawing—and came away feeling like I'd just had the best kind of therapy session. Which, as it turns out, is exactly what Sam's work is all about.Sam joined me from her studio in Dumbo, and what started as a casual chat about pickleball evolved into a masterclass on using art as a tool for presence, sense memory, and genuine human connection. It’s crazy I get to speak to people like this every

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55:34

The Dollar Tree Revolutionary: From Introvert Drawing...

Draw Me Anything with Jason Chatfield ·

2025/06/25

How Beth Spencer Started an Art Movement with a Five-Minute SketchI need to tell you about Beth Spencer —not because she asked me to (she didn't), but because watching her work on Substack these past few years has been like watching someone perfect the art of making strangers feel less alone with a pencil and a really good attitude about being terrible at things.Beth runs the Introvert Drawing Club, which might be the most honest newsletter title in the history of newsletters. No grandiose promises

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62:22

From Bad Stand-Up to Beautiful Art: The Nishant Jain...

Draw Me Anything with Jason Chatfield ·

2025/06/15

Thank you to those of you who tuned in to my live stream with Nishant Jain! If you missed it live, I hope you enjoy the replay above.Join me next Tuesday & Friday for my next TWO live episodes with Best-selling Author and Artist Austin Kleon & Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes.Tiny People, Big Ideas: My Drawing Lesson with Nishant JainYesterday, I had the pleasure of talking with my friend Nishant Jain, the brilliant mind behind The SneakyArt Post, and honestly, my tiny nugget

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54:33

Matt Ruby on Comedy, Mindfulness, and Why Algorithms...

Draw Me Anything with Jason Chatfield ·

2025/06/10

Yesterday, I sat down with Matt Ruby, a comedian who's somehow managed to turn drug experimentation into art, philosophical wisdom into punchlines, and crowdwork critique into a manifesto. What started as a chat about joke writing quickly devolved into an exploration of why we're all slaves to Chinese algorithms, how meditation is the antidote to everything, and why tension might just be comedy's secret weapon.Matt's an inventive comic. He once did a special called Substance where he performs the

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36:03

Ann Telnaes: Talking Musk VS Trump & Freedom of...

Draw Me Anything with Jason Chatfield ·

2025/06/06

Two Megalomaniacs Walk Into a Democracy: Ann Telnaes on Cartoons, Chaos, and Why We Can't Look AwayEarlier today, I got to speak with Ann Telnaes, 2025 Pulitzer Prize winner and one of the most fearless voices in political cartooning. (Also, one of my favourite people in the world.) We discussed the urgent question: “How do you document democracy's slow-motion car crash when two unhinged maniacs are fighting over the steering wheel?”New York Cartoons is a reader-supported publication. To receive new

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62:52

Comedy Over Tragedy: Austin Kleon's Masterclass On...

Draw Me Anything with Jason Chatfield ·

2025/06/04

Thank you The Bob, Brendan Leonard, Tammy Evans, Bill Cusano, Mariana Marques, and the 500 others who tuned into my live video with Austin Kleon yesterday! New York Cartoons is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Join me for the next one on Friday at 11am EDT — I’ll be talking & drawing with special guest, Two-Time Pulitzer Prize-winning Cartoonist, Ann Telnaes!About The Guest:Austin is the New York Times bestselling

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