Episodes

  • 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
  • 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
  • The King of Late Night TV, Steve Vizard

    The King of Late Night TV, Steve Vizard
    Apr 5 2026
    Steve Vizard is Australia's Johnny Carson. Tonight Live with Steve Vizard was Australia's Tonight Show in the 1990s, after Vizard had previously created two of Australia's biggest-ever sketch comedy shows. 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. Steve joined Josh to recount tales of the golden age of late-night television, the mishaps of hosting a live show every night, Kimmel, Colbert and how broadcast TV is evolving… and Andy Lee interrupts the podcast briefly.
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    45 mins
  • A Black Muslim Comic & Gay Jew Walk Into an Uncomfortable Conversation

    A Black Muslim Comic & Gay Jew Walk Into an Uncomfortable Conversation
    Apr 3 2026
    Zainab Johnson is a black muslim female New Yorker with a half-million instagram fans and the title of Variety magazine’s Top 10 Comics to Watch. 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. Zainab joined Josh to school him on comedy, Islam, and marsupial reproductive biology. Her Amazon Prime special is ‘Hijabs Off’
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    1 hr and 4 mins