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Uncomfortable Conversations with Josh Szeps

Josh Szeps
Australia
Donald Trump
Artificial Intelligence
Israel
Climate Change
Free Speech
Mental Health
Social Justice
Australian Politics
Social Media
Democracy
Iran
Cancel Culture
Education
Zionism
Food Safety
Immigration
Identity Politics
China
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 weeklyEpisodes561Founded11 years ago
Number of ListenersCategories
Society & CultureComedyComedy Interviews

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Artwork for Uncomfortable Conversations

Latest Episodes

Is there any room left for the political centre, or has it been swallowed by two competing extremes with nothing but contempt for the middle?

Josh chats with comedy writer and author of I Might Be Wrong, Jeff Maurer, for a wide-ranging conversation ... more

It's a quarter-century since 9/11. What do we need to understand about its legacy, so as to handle the next quarter-century better?

Josh was a college student visiting the World Trade Towers the summer before the September 11th attacks. In this marat... more

Has a secret in your ancestry ever changed who you are?

Imagine being a non-Jewish comedian who suddenly finds out he's Jewish. What do you do? You put on a comedy show on the site of the worst antisemitic terrorist attack in the country's history. ... more

A sex scandal involving star players for the Sydney Swans has rocked Australia. Coinciding with a spate of violence against women, the country is revisiting its all-too-familiar conversation about how “Men must do better”.

What does that look like, ... more

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Recent Guests

David Rose
Comedian, Jewish Australian performer
Independent / UK‑Australian circuit
Episode: Jewish Comedy at the Bondi Attack
Ben Vasiliou
CEO of The Man Cave, author of Better Man, Reclaiming Masculinity for Good
The Man Cave
Episode: Are Men Toxic?
Anthony Colangelo
Space nerd and space expert, guest on the episode
Space industry analyst
Episode: What is Elon Up To?: An Idiot’s Guide to Space and Why You Need to Pay Attention
Glenn Loury
American academic and cultural commentator
Brown University, The Glenn Show (Substack)
Episode: Glenn Loury: Are we censoring ourselves to death?
Suey Park
Asian American anti-racism activist introduced in the original Colbert interview
Episode: Jason Arday, Suey Park & the Identity Hunger Games
Jason Arday
Cambridge University professor discussed posthumously as the subject of the identity politics debate
Cambridge University
Episode: Jason Arday, Suey Park & the Identity Hunger Games
Jon Ronson
Author and journalist known for So You've Been Publicly Shamed and The Men Who Stare at Goats
Author/Journalist
Episode: How the Public Shaming Machine was Built with Jon Ronson
Peter Beinart
Author and journalist discussing Zionism and anti-Zionism
Columnist and author
Episode: The Case Against Israel with Peter Beinart
Matt Jones
Political strategist and speechwriter for the British Conservative Party (former)
Branding and political strategy
Episode: How Branding Replaced Facts in Politics

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
  • Ryan Martin

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

    Apple Podcasts
    5
    LaylaMG5
    Australia2 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
  • Intellectual and, at times, hilarious

    Josh is an inspiration for having more of these types of conversations in my life. For me, his show is a really good reminder to be curious and open-minded rather than defensive when you meet someone with a dissenting opinion. I don’t agree with all of his views, but isn’t that the whole point?

    Apple Podcasts
    5
    Wildrose419
    Australia3 months ago
  • Smooching Butt!

    Taibbi became a tool of Trump and Elon and you smooched his butt without challenging him. Disappointing. The old Josh would have done way better.

    Apple Podcasts
    4
    80'sVillager
    United States3 months ago
  • Smiling

    Thank you for the conversation with Sarah. Unsettling and empowering all at once.

    Apple Podcasts
    5
    thermosprotection1
    United States3 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.

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.
Why We Don’t Believe Boys: Female Grooming & the Male Teen
Q: I mean, at what point were you actually having sex, and was that a-
The guest explains it began within weeks after the relationship started, describing coercion and the sense of being on top of the world while misperceiving it as love, and later recognizing the abuse.

Audience Metrics

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

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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. Quillette Podcast
3. Blocked and Reported
4. The Moynihan Report
5. The Glenn Show

How many episodes of Uncomfortable Conversations are there?

Uncomfortable Conversations launched 11 years ago and published 561 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. David Rose
2. Ben Vasiliou
3. Anthony Colangelo
4. Glenn Loury
5. Suey Park
6. Jason Arday
7. Jon Ronson
8. Peter Beinart

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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