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Uncomfortable Conversations with Josh Szeps

Josh Szeps
Australia
Donald Trump
Artificial Intelligence
Climate Change
Israel
Free Speech
Mental Health
Australian Politics
Social Justice
Social Media
Iran
Democracy
Cancel Culture
Education
Zionism
Food Safety
Immigration
China
Identity Politics
Comedy

The world has never been more connected. Yet never more divided. We yell at each other from inside our echo chambers. But change doesn’t happen inside an echo chamber. It’s time to get out, to stretch our legs, to step on some land mines. It's time to have an uncomfortable conversation with Josh Szeps.

A DM Podcast

PublishesTwice weeklyEpisodes568Founded11 years ago
Number of ListenersCategories
Society & CultureComedyComedy Interviews

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Artwork for Uncomfortable Conversations

Latest Episodes

Every human mind is a propaganda machine. It manufactures certainty, reinforces old narratives, and keeps us loyal to beliefs that no longer serve us. In an era of infinite information and AI-generated content, these internal distortions make it tric... more

What do we actually owe each other in a society trying to hold pluralism, free speech, and real religious and ethnic tension together at the same time?

Josh sits down with comedian, writer, and Crikey columnist Sami Shah, born Muslim in Pakistan, wh... more

When you read news about a data breach which might have exposed your information, do you even care? Who’s behind all this hacking: China, Russia, or a nerd in his parents’ basement? Are our water and electrical systems at risk? And is A.I. going to m... more

Today we’re sharing a bonus episode from The Moynihan Report.

William Shatner sits down with Michael Moynihan in Los Angeles for a conversation about life, time, and knowledge. They talk about death, God, AI, Blue Origin, The Intruder, and the rele... more

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Recent Guests

Sami Shah
Pakistani-Australian comedian, writer, and commentator
Festival of Dangerous Ideas / Crikey / News Weekly
Episode: Free speech, hate speech, and the limits of Liberal tolerance with Sami Shah
Assadi Youssef
Ethical hacker and security advisor
Independent security consultant advising banks and critical infrastructure
Episode: Who's hacking you right now? with ethical hacker Assadi Youssef
William Shatner
Actor and public figure discussing career, aging, and creativity
Episode: William Shatner Doesn’t Want to Die, from The Moynihan Report
Jonathan Haidt
Social psychologist; author of The Righteous Mind and The Coddling of the American Mind
New York University
Episode: Social media broke our ability to agree, with Jonathan Haidt
Megan Phelps-Roper
Former member of Westboro Baptist Church; journalist and activist
Westboro Baptist Church (former); journalist/activist
Episode: “So… *Does* God Hate F*gs?” with Megan Phelps-Roper
Jeff Maurer
Comedy writer, publisher of the I Might Be Wrong substack, former writer on John Oliver
I Might Be Wrong / John Oliver team
Episode: Is there any Room left for moderates? With Jeff Maurer
Jon Stewart
Host of The Daily Show providing reflection on the rebound of satire after 9/11
Comedy Central
Episode: JUST JOSH: The Unlearned Lesson of 9/11
David Letterman
Late-night host providing archival context on the first back-at-work broadcast after 9/11
CBS/Letterman era
Episode: JUST JOSH: The Unlearned Lesson of 9/11
David Rose
Comedian, Jewish Australian performer
Independent / UK‑Australian circuit
Episode: Jewish Comedy at the Bondi Attack

Host

Josh Szeps
Host known for leading uncomfortable conversations on politics, culture, and society; frequently engages with guests to unpack controversial topics.

Reviews

4.4 out of 5 stars from 3.1k ratings
  • 9/11 episode

    Thoughtful. Thought-provoking.

    Thank you.

    Apple Podcasts
    5
    thermosprotection1
    United States23 days ago
  • Rage bait doesn’t live up to promise of a complex discussion

    Interesting and valuable concept - the idea that we should be able to have uncomfortable conversations that challenge mainstream groupthink. But Josh is not a good interviewer - frequently interrupting guests before they can get a thought out and one-upping them to try and prove ?intellectual superiority. His style is quite hostile and pugilistic, so I don’t feel that in practice these conversations are truly thought provoking or able to get to the nuance/complexity of the topic.

    Apple Podcasts
    2
    Sarah6538375
    Australiaa month ago
  • Einstein Wilf seems like the smartest person in the room

    Excellent truth . Refreshing to hear the voice of someone who had a seat at the table.

    Josh, on the other hand seems to reflexively Westplain. It’s a pattern.

    Apple Podcasts
    5
    lindaincharlotte
    United Statesa month ago
  • Ryan Martin

    This was the best interview for every person in a parenting role.

    Apple Podcasts
    5
    LaylaMG5
    Australia3 months ago
  • Hated by Both

    It’s great to read reviews that hate you from sides of the isle. Please keep contributing to conversations regardless of what your audience wants to hear. Thanks Josh!

    Apple Podcasts
    5
    Hooked On Nature
    Australia3 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests bring strong expertise; the debates feel nuanced rather than partisan.
The host asks tough questions but stays civil, keeping conversations constructive.
Listener sentiment varies; some episodes feel pointed or provocative, others deeply insightful.
Production quality and editing are generally tight, making complex topics accessible.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Is there any Room left for moderates? With Jeff Maurer
Q: How do you compare the Harris–Cheney collaboration with the El-Sayed–Piker dynamic?
They contrast foundational principles transcending policy with explicit policy alignments, arguing that cross-ideological collaborations can signal deeper values about democracy, institutions, and national identity.
Jewish Comedy at the Bondi Attack
Q: How did your great‑grandfather influence your approach to comedy and Jewish identity on stage?
His legacy frames the tension between tradition and modernity; I use personal lineage to navigate stereotypes, while also acknowledging the harm past caricatures caused, and I strive to fuse history with contemporary satire.
Jason Arday, Suey Park & the Identity Hunger Games
Q: Why cancel Colbert? What did you hope to achieve with that?
The aim was to signal accountability and show that such jokes about people of color have real, lasting consequences, while also highlighting the broader pattern that Asian Americans are often treated as a punchline and that there should be more serious discussion around representation and respect.
The Case Against Israel with Peter Beinart
Q: How do you think about the idea that all you really need to know about the current conflict is what each side would do if they had total power?
The speakers discuss the difference between hypothetical power dynamics and actual policy outcomes, noting that leaders' actions (e.g., Netanyahu or Hamas) reveal much about political priorities, while stressing the importance of separating moral judgments from strategic calculations.
How Branding Replaced Facts in Politics
Q: What exactly unites Donald Trump and Barack Obama?
Branding and the ability to tell a compelling narrative that defines themselves and resonates emotionally with people, more than any single policy detail.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Uncomfortable Conversations

What is Uncomfortable Conversations about and what kind of topics does it cover?

The show centers on provocative, candid conversations that challenge conventional wisdom across politics, culture, and society. Episodes frequently feature executives, journalists, academics, and insiders who bring expert context to hot-button topics such as free speech, gender, parenting, education, and political branding. The host steers conversations toward practical implications and real-world dynamics, often highlighting how narratives shape public discourse more than facts. Listeners can expect thorough debate, diverse viewpoints, and a willingness to tackle controversial subjects with curiosity, civility, and a bias toward unpacking uncomfortable questions. A notable strength is its ability to attract high-profile guests from politic... more

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Which podcasts are similar to Uncomfortable Conversations?

These podcasts share a similar audience with Uncomfortable Conversations:

1. Conversations with Coleman
2. Making Sense with Sam Harris
3. The Unspeakeasy With Meghan Daum
4. Quillette Podcast
5. The Moynihan Report

How many episodes of Uncomfortable Conversations are there?

Uncomfortable Conversations launched 11 years ago and published 568 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Uncomfortable Conversations?

Recent guests on Uncomfortable Conversations include:

1. Sami Shah
2. Assadi Youssef
3. William Shatner
4. Jonathan Haidt
5. Megan Phelps-Roper
6. Jeff Maurer
7. Jon Stewart
8. David Letterman

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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