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Uncomfortable Conversations with Josh Szeps

Fmr John Oliver Writer on Bias, Blackface & Making Sense of the News

Uncomfortable Conversations with Josh Szeps

Josh Szeps

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

4.5905 Ratings

🗓️ 9 February 2026

⏱️ 117 minutes

🧾️ Download transcript

Summary

Has our culture had a grown-up conversation yet about race and gender? Or did the media flip from the casual bigotry of the 20th century to the censorious hysteria of the 2010s in a way that empowered the rise of the New Right? And what was it like to work as a comedy writer on a hit progressive comedy show as the culture underwent The Great Awokening? Jeff Maurer was a writer on Last Week Tonight with John Oliver for its first six seasons. He left in 2020 after feeling its editorial angle had become too ideologically captured. Now, Jeff has a wildly popular political-satire Substack, “I Might Be Wrong”. Josh intended to chat with Jeff to help make sense of Minneapolis, Epstein, ICE, the 2020 election ballots, Don Lemon’s arrest and, of course, the Melania documentary. There’s been a lot, lately. But this conversation evolved into a far more fascinating and funny discussion about what the controversies over blackface and transgenderism can teach us about how the media lost its way; about whether we’ve lost the ability to cover the news - and to satirise it - without preaching to the choir. Follow Jeff’s comedy writing below at www.imightbewrong.org

Transcript

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0:00.0

Gahey, humans.

0:06.0

Welcome to the safe space for dangerous ideas.

0:09.0

Here's a dangerous question for you.

0:12.0

Has our culture ever actually reckoned, intelligently, had a grown-up conversation about the newer taboos, especially around race and gender

0:24.4

and transgenderism. Or did the media just sort of flip from the casual bigotry that it had in

0:31.3

the 20th century to the censorious hysteria of peak woke in a way that actually empowered the rise of the new

0:40.6

riot and robbed us of the ability to try to think carefully about issues of importance

0:46.2

to cultural and social cohesion. One person who was at the coal face of the Great

0:52.2

Awakening and trying to think about this in the way that these ideas were articulated to the public is Jeff Moorah, who was a comedy

0:59.1

writer on one of the biggest progressive satirical shows in America last week tonight with

1:04.9

John Oliver from its first season right through until 2020 when he left the show because

1:10.0

he felt that it had become somewhat

1:11.5

ideologically captured and perhaps for personal reasons as well. Now Jeff has a wildly popular

1:18.3

political satire substack, a comedy substack called I Might Be Wrong and I had planned to chat with

1:23.9

Jeff because I've been a little bit out of the news loop. I wanted his thoughts on Minneapolis and Epstein and ICE and the 2020 election ballots in Georgia being seized and

1:34.5

Don Lemon's arrest and the Melania documentary, of course, the most important news. But we ended up

1:41.6

talking about a much more fascinating subject, which is the one that I just

1:45.5

articulated.

1:46.5

Like, we sort of address blackface and transgenderism as two examples of maybe where the

1:54.3

media lost its way, where we lost the ability to cover the news and to satirize the

2:00.5

news without pandering to our audiences

2:03.0

and preaching to the choir. I hope you enjoy as much as I did. The one, the only, Jeff

...

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