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Uncomfortable Conversations with Josh Szeps

“Being a Satirist in Censorious Times” with cartoonist Jason Chatfield

Uncomfortable Conversations with Josh Szeps

Josh Szeps

Society & Culture, Comedy Interviews, Self-improvement, Comedy, Education

4.5905 Ratings

🗓️ 6 November 2025

⏱️ 43 minutes

🧾️ Download transcript

Summary

Zohran Mamdani has just been elected mayor of New York, parachuting onto a political terrain more polarised and energised than it's been since the 1960s. How do you maintain an independent satirical voice in such vitriolic times?

Joining Josh from NYC on a Substack Livestream the day after the mayoral election is Jason Chatfield, one of the world’s most successful cartoonists. Jason was implausibly young when he was tapped to run Australia’s longest-running and most iconic comic strip, Ginger Meggs. After moving to the States, he won acclaim for iconic cartoons in The New Yorker, Esquire, Variety and Mad Magazine, and he served as the president of the National Cartoonists Society. Now, he's independent, on Substack.

In an age of algorithms, outrage and censorship, how far can creative people go? Politically, financially, and personal fulfillmentilly, it's a conundrum for anyone pursuing an independent creative life. Jason joined Josh from his home in Manhattan to talk Mamdani, Trump, satire, authenticity, perfectionism... and the future of free expression.

Transcript

Click on a timestamp to play from that location

0:00.0

Gooday, humans. Welcome to the safe space for dangerous ideas. One of the most dangerous and

0:08.6

uncomfortable conversations that independently employed creative artists have with themselves in this

0:14.6

climate is how far they should push the envelope. How far is too far? How self-expressed can we be? How authentic can we be versus how much

0:23.5

should we count out to the opinions of our peers, the opinions of our leaders and the mandates

0:29.6

of the algorithms that drive so much of our income? Today's guest is arguably the most

0:35.5

successful cartoonist in the world.

0:39.1

He's an Aussie who lives in New York City.

0:41.8

And at the age of 23, he was handed the keys to Australia's longest running, most iconic, most famous newspaper comedy comic strip.

0:49.8

If you think of things like Dilbert and Dennis the Menace and Calvin and Hobbs and Garfield and peanuts and so on.

0:55.9

In Australia we had Ginger Megs.

0:58.7

And Jason wrote and drew Ginger Megs for almost 20 years.

1:04.8

It was syndicated all over the world.

1:06.7

He moved to New York City and became a big deal in American cartooning as well.

1:11.0

He ended up the president of the National Cartoonists Society,

1:15.3

essentially the chief grand pooh bar of satirical cartoonists in the United States.

1:20.9

So how do you sustain a career independently on Substack when your craft is so seemingly old-fashioned as writing and

1:30.7

illustrating a comic strip. Jason joined me for a substack live on the day that Zoran

1:36.4

Mamdani became the mayor-elect of New York City, so I wanted his thoughts about politics,

1:42.5

about satire, about the vibe of the city with Mamdani coming in

1:46.6

about how you construct an authentic creative life in this crazy world of ours

1:51.7

and resist the forces of censorship from the powerful and from your peers.

1:56.6

This is a premium episode, so you will get a healthy and interesting chunk of it, whether you

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