• 53 minutes 43 seconds
    Should You Be A Nationalist?

    Does nationalism have to be xenophobic or racist? What would it mean to be a nationalist who isn’t a blood-&-soil bigot but a pluralistic liberal? How can multicultural societies like ours sustain strong national identities? Could we actually reinvigorate democracy with a big ole dose of chest-thumping and flag-flying?

    David Moscrop, is a Canadian writer, academic and public intellectual. He has a PhD in Political Science and was a regular contributor for The Washington Post.

    He joined Josh ahead of a trip to Australia to discuss national identity on a dog-eat-dog planet, the left’s overreach in the culture wars, Canadian truckers, right-wing anti-vaxxers, multiculturalism, jingoism, how all of us can be more coherent as a democratic unit, and most importantly, why Love Actually is a terrible film.

    David Moscrop appears at Melbourne Writers Festival (7-10 May) and Sydney Writers' Festival (17-24 May).

    7 May 2026, 7:00 pm
  • 36 minutes 50 seconds
    Josh vs the News: Trump Cancels "Project Freedom!"

    The latest chaotic development under “Operation Epic Fury” has continued to show the catastrophic strategic position the United States has found itself in. But it could be worse! It’s not like the Iranians know about the midterms, and the impending electoral annihilation coming for Trump if this latest oil shock isn’t resolved. Oh wait…

    Josh breaks down the the failure of “Project Freedom”, how Iran has discovered an asset even more valuable than nuclear weapons, and why the rest of the world is about to pay a tremendous price for America's miscalculation.

    6 May 2026, 2:49 am
  • 1 hour 24 minutes
    JIMMY CARR RETURNS!

    Jimmy Carr is one of the most successful stand-up comics on earth (and one of our most recurring guests).

    His hilarious, brutal crowd work is a viral sensation, and his television credits include hosting some of the UK’s longest running panel shows such as 8 Out Of 10 Cats, Big Fat Quiz Of The Year and his smash-hit Netflix specials, Natural Born Killer, and His Dark Material.

    Whilst touring Australia for his latest live show, JIMMY CARR: LAUGHS FUNNY, he joined Josh in the flesh at the Uncomfortable Conversations studio to discuss revolution, A.I, fame, hair transplants, and why some things just can’t be fixed.

    His new podcast is ‘Jimmy Carr: Crowd Work’ (https://open.spotify.com/show/72DxXJcIZGKEjX5hOoE2hk?si=e216f378b7b84f3f).

    4 May 2026, 7:00 pm
  • 1 hour 16 minutes
    Why Smart People Make Dumb Choices

    Life’s biggest decisions are always the most Uncomfortable. Should you have a baby? Should you quit your job? Should you move to a new country? Should you drop acid?

    Anytime you’re faced with a decision that is likely to change who you are, you’re faced with a unique conundrum: The person you’ll be - who’ll judge whether you made the right call or the wrong one - is future you.

    They’re a different person than Future You would be if present-day You had made the opposite decision. Still with me?

    How are we supposed to decide how to lead a good life, if we can only ever know what we know right now (but we need to make decisions now that will affect who we become in the future)?

    Laurie Paul is a professor of philosophy and cognitive science at Yale University who’s a leading expert on the counterfactual analysis of causation and the concept of transformative experience.

    She joins Josh to discuss how we judge whether to become a parent, how your preferences get scrambled by addiction, why atheists and religious people are secretly terrified of each other’s epiphanies, what cochlear implants tell us about identity, A.I., psychedelics, and what it means to make a choice in a state of radical ignorance… about who you’ll be once you’ve made it.

    30 April 2026, 7:00 pm
  • 2 hours 4 minutes
    'Truth' in an Age of A.I.

    What will reality feel like when we receive most of it via all-knowing machines?

    Our shared understanding of the world has been fractured by social media’s echo chambers of news, entertainment, misinformation, and distraction. Could A.I. help re-establish common facts? Or will it only make the truth even slippier?


    Steve Rosenbaum is an Emmy-winning former television news producer, TED Resident and boss of the NYC Media Lab. He joins Josh to explore the death of traditional news, why TikTok is so addictive, how young people think about trustworthiness... and how to fortify facts in a world of slop.

    Steve's new book is "The Future of Truth: How AI Reshapes Reality". 

    28 April 2026, 2:03 am
  • 52 minutes 1 second
    Philosopher A.C. Grayling in the Most Mind-Expanding Episode of the Year

    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.

    23 April 2026, 7:00 pm
  • 1 hour 51 minutes
    Josh vs the Anti-Abortion Activist

    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.

    20 April 2026, 7:00 pm
  • 46 minutes 56 seconds
    BLOCKADE COUNTDOWN: What's the End Game?

    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.

    16 April 2026, 7:00 pm
  • 44 minutes 13 seconds
    Josh vs the News: Blockade Games, Orban Ousted, & Elon Notices Australia

    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.

    15 April 2026, 4:47 am
  • 1 hour 15 minutes
    "Nuremberg" & the Psychology of Evil

    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.

    13 April 2026, 7:00 pm
  • 37 minutes 3 seconds
    Writing for 'SNL' with Sam Jay

    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.

    9 April 2026, 7:00 pm
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