Episodes

  • Josh vs the Anti-Abortion Activist

    Josh vs the Anti-Abortion Activist
    Apr 20 2026
    For an issue we don’t normally know how to talk constructively about, can Josh and one of the most outspoken anti-abortion activists model what a genuine, but respectful, disagreement can actually look like? Joanna Howe is best-known for her viral videos on YouTube and social media debating people in the street about abortion, confronting politicians outside their offices, and smacking down pro-life politicians for not being pro-life enough. She's a law professor and a Catholic whose hundreds of thousands of followers cheer her on as she owns the libs and argues for abortion to be illegal because it is murder from the moment of fertilisation. She joins Josh to have a rational debate about an emotional topic, and try in some small way, to help you have less toxic and more constructive conversations of your own. You can find Josh’s previous conversation with the American family-values anti-surrogacy activist Katie Faust, here.
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    1 hr and 51 mins
  • BLOCKADE COUNTDOWN: What's the End Game?

    BLOCKADE COUNTDOWN: What's the End Game?
    Apr 16 2026
    What is the end game in Iran? What is the blockade achieving? What cards does Iran still hold? Last week, the end was in sight with a two-week ceasefire. Then talks in Pakistan between the US vice president and the Iranians went nowhere, and Trump suddenly imposed a blockade. Since Monday, U.S. forces say they’ve now completely halted all economic trade leaving Iran’s ports. Iran say they’ll retaliate if the blockade continues. Where does the escalation lead? Does Trump have anything left up his sleeve? What exit ramps are there for either side? Steven Simon served in the US State Department, where he specialised in the Middle East and counter-terrorism on President Clinton’s National Security Council. President Obama brought him back into the White House to serve as the NSC’s Senior Director for the Middle East and North Africa. He’s a leading world expert on Iran and co-wrote a book in 2011 called “The sixth crisis: Iran, Israel, America and the rumors of war.” His most recent book is “Grand Delusion: The Rise and Fall of American Ambition in the Middle East.” Steven joined Josh to explain the logic (or illogic) of Trump’s blockade... and what thirty years of shaping US policy in the Middle East has taught him about how this conflict is likely to end.
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    47 mins
  • Philosopher A.C. Grayling in the Most Mind-Expanding Episode of the Year

    Philosopher A.C. Grayling in the Most Mind-Expanding Episode of the Year
    Apr 23 2026
    Today, a delightful and scintillating and inspiring and disconcerting and thought-provoking and discombobulating and many-other-multi-syllabic words-ing romp with one of the most celebrated philosophers in the English-speaking world. A.C. Grayling is a British philosopher who has written more than thirty books on everything from the nature of consciousness to the history of freedom to what it means to live well. Now, he is warning about the fragility of liberal democracy and on a speaking tour to Australia he joined Josh to discuss the crisis of meaning in the West, the rise of authoritarianism, and what remains of the self when the machines get smart too.
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    52 mins
  • Josh vs the News: Blockade Games, Orban Ousted, & Elon Notices Australia

    Josh vs the News: Blockade Games, Orban Ousted, & Elon Notices Australia
    Apr 15 2026
    On this week's thrilling instalment of the world's favourite livestream, Josh vs the News: •⁠ ⁠Hormuz gets a Big, Beautiful naval blockade! •⁠ ⁠How Viktor Orbán was defeated by a ranch full of zebras! •⁠ ⁠and why is Elon tweeting about Australia this week? Plus, Professor Szeps answers your questions: "why is US petrol expensive if America doesn't import Iranian oil?" Tune in live every week at uncomfortableconversations.substack.com.
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    44 mins
  • "Nuremberg" & the Psychology of Evil

    "Nuremberg" & the Psychology of Evil
    Apr 13 2026
    Were top Nazi leaders mad? Were they evil? Were they like religious fundamentalists, committed to a deranged ideology? Or were they just amoral narcissists grasping for power in the wrong place at the wrong time? Jack el-Hai wrote the book which became the movie "Nuremberg", in which Russell Crowe plays Hermann Göring. In Nuremberg jail, awaiting trial, 22 senior Nazis were interviewed by a young U.S. Army psychiatrist. Psychiatrist Dr Douglas Kelly was only supposed to assess the Nazis’ mental fitness to stand trial. But he became obsessed with identifying a “Nazi personality”. He spent months with Goering, the man who was to succeed Hitler, hunting for traits or disorders that could identify who might commit such atrocities in the future. His private notes were kept secret by Kelly’s family until they released them to Jack. He joined Josh to share what he learned, and what we all should understand about evil.
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    1 hr and 15 mins
  • Writing for 'SNL' with Sam Jay

    Writing for 'SNL' with Sam Jay
    Apr 9 2026
    Sam Jay is an Emmy-nominated comedian and former writer on Saturday Night Live. She walked away from becoming an SNL cast member to host her own HBO talk show about uncomfortable conversations called 'Pause with Sam Jay'. She has a Netflix stand-up special, an HBO stand-up special, and her latest show is We The People, nominated for Best Comedy Show at the Edinburgh Comedy Awards last year. This is the final episode of the Uncomfortable Conversations Comedy Festival extravaganza. Josh headed to Melbourne for a ten-hour Substack Live marathon with five of the greatest comedians. Sam joins Josh to wrestle with her gayness, her blackness, her americanness, her creativeness, her differentness and sameness.
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    37 mins
  • BREAKING: Trump Always Chickens Out (Thank F*ck)

    BREAKING: Trump Always Chickens Out (Thank F*ck)
    Apr 8 2026
    Donald ‘Taco’ Trump has once again lived up to his nickname. After weeks of escalating threats to obliterate Iran's power plants, bomb them back to the Stone Age, and declare that "a whole civilization will die tonight," the President has blinked. Again. Josh breaks down the entire chaotic timeline of Trump's Iran strategy, and argues that these past two weeks may have written Trump's political epitaph. The crudeness, the bombast, the "you crazy bastards" diplomacy has become so unseemly that Trumpism itself may finally be toast. Plus: Why the Artemis moon mission matters (stop asking why we're going back), what Survivor teaches us about coalition building, and why jihadists really shouldn't get nukes. Thank f*ck for Taco.
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    55 mins
  • Dave Hughes Has a Problem With Josh

    Dave Hughes Has a Problem With Josh
    Apr 7 2026
    Dave Hughes is a legend of Australian television, radio and stand-up comedy. He has been so ubiquitous on TV and radio for the past 30 years that almost every Australian has a Dave Hughes impersonation. This episode is part of the Uncomfortable Conversations Comedy Festival extravaganza. Josh headed to Melbourne for a ten-hour Substack Live marathon with five of the greatest comedians. You’ll get a new episode every 48 hours for the first two weeks of the biggest comedy festival in the world. He joined Josh to discuss being poor, being rich, getting famous, and insulting the radio shock jock Kyle Sandilands.
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    1 hr and 21 mins