PodcastsComedyUncomfortable Conversations with Josh Szeps

Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
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466 episodes

  • Uncomfortable Conversations with Josh Szeps

    WTF? Gladiator Battles on the White House Lawn: How MMA & the Manosphere Took Over America (& the White House)

    06/11/2026 | 13 mins.
    On Sunday, mixed martial arts fighters will beat the crap out of each other in a 90-foot-tall Ultimate Fighting Championship cage on the South Lawn of the White House. Senator John McCain once denounced the sport as "human cockfighting". President Trump loves it so much he's made it a centrepiece of the United States' 250th birthday celebrations.
    Trump isn't alone. Not long ago, MMA was considered too violent even to be offered alongside pornographic movies on pay-per-view cable. Now, it's a mainstream juggernaut. How did this happen? The story is an insane saga involving Las Vegas, Covid, Joe Rogan, MAGA and the spectacular ambition of one man: Dana White. 
    White, who built the UFC, is on the cover of TIME magazine this week. His profile was written by TIME's senior sports correspondent, Sean Gregory, who visited with White, Trump and legendary Hollywood agent Ari Emanuel for his piece.
    Sean Gregory joins Josh to explain the wild origins of MMA, the alliances that turbocharged it, Dana White's role in delivering young men to MAGA, and what the UFC tells us about masculinity, the manosphere, and where America finds itself today.
  • Uncomfortable Conversations with Josh Szeps

    "Smile! Civilisation is Collapsing" with Sarah Wilson

    06/08/2026 | 1h 12 mins.
    In a world of catastrophic fires, record floods, collapsing democracies and rising unrest, our lives have rarely felt more precarious. So how do we keep living meaningfully through it? And if (or when) it all comes apart, what kind of people do we want to be?
    Sarah Wilson is a New York Times bestselling author, whose new book, ‘I Eat the Stars’, chronicles how we might live meaningfully, sanely, and hopefully, survive the end of civilisation.
    Live at the Wheeler Centre in Melbourne, Sarah sits down with Josh to discuss how we face difficult truths without succumbing to doom, whether rumours of humanity’s death are greatly exaggerated, and how oddly liberating it is to recognise you are useless to capitalism.
  • Uncomfortable Conversations with Josh Szeps

    Matt Taibbi, America's Top Gonzo Journalist, on How the Media Lost Its Mind

    06/01/2026 | 1h 41 mins.
    Get 30% OFF an Annual Uncomfortable Conversations Subscription at https://uncomfortableconversations.substack.com/subscribe/sanity

    What happened to the news media? What does it have to do with why Hillary Clinton couldn’t fill a room, while Trump filled stadiums? Did diversity kill objective journalism? And what does a journalist who lived in the Soviet Union think of free speech in the West today?

    Matt Taibbi became a rockstar reporter covering Trump’s first election campaign for Rolling Stone. He went on to cover huge stories like Twitter’s pre-Elon censorship regime and the misinformation around Trump’s ties to Russia. Matt joins Josh in New York City for this in-the-flesh livestream about American politics, algorithms and why, despite it all, he’s optimistic about what comes next.
  • Uncomfortable Conversations with Josh Szeps

    “What the Hell Happened to L.A.?” with Meghan Daum

    05/28/2026 | 1h 21 mins.
    Los Angeles was once the city where people went to reinvent themselves. Space, sunshine, stardom. How did it become the city where people go to disappear into homeless tent encampments?

    Meghan Daum is one of America’s sharpest cultural essayists, a former LA Times columnist and a longtime Angelino.

    While Josh is in L.A., he and Meghan livestreamed from the Hollywood Hills in this Memorial Day conversation about what, exactly, Los Angeles is (city? county? megalopolis?), the decline of showbiz, the 2025 wildfires, California Democrats, dog abuse, addiction, incarceration, and why Spencer Pratt, a reality TV star from The Hills, might be the most honest candidate running for mayor.
  • Uncomfortable Conversations with Josh Szeps

    Where Does Anti-Zionism End and Anti-Semitism Begin?

    05/25/2026 | 1h 46 mins.
    Is it possible to criticise Israel without being anti-Semitic? How do we even know if you cross that line?
    It’s a question that has divided dinner tables, ended friendships, and split the left in half since October 7th, and with recent events, is no longer a theoretical debate. The oldest hatred in human history is once again at the surface.
    Israeli President and Prime Minister Shimon Peres called David Harris “the foreign minister for the Jews”, having spent fifty years as one of the most prominent Jewish diplomats in the world. He served as CEO of the American Jewish Committee, has met with heads of state on every continent, and has just published Antisemitism: What Everyone Needs to Know with Oxford University Press. He grew up in a family that lived through Soviet communism, Nazi-occupied France, and the expulsion of Jews from Libya. He knows what happens when the shapeshifting virus of anti-Semitism comes out of hibernation.
    He joined Josh in the Uncomfortable Conversations studio to discuss why anti-Semitism always ends in lethality, why Israel has become the Jew among nations, what the left gets catastrophically wrong about October seventh, and why, after fifty years of working for peace, he still considers the existence of Israel nothing short of a miracle.
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About Uncomfortable Conversations with Josh Szeps
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  
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