Skip to content
PodcastsComedyUncomfortable Conversations with Josh Szeps

Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
Latest episode

495 episodes

  • Uncomfortable Conversations with Josh Szeps

    Is there any Room left for moderates? With Jeff Maurer

    2026/09/14 | 1h 16 mins.
    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 about the collapse of moderate politics in America. They dig into the strange case of Abdul El-Sayed campaigning with Hasan Piker in the Michigan primary and why that alliance, once worn as a badge of honour, is now something El-Sayed can't stop running from. They also cover Milo Yiannopoulos's deportation, the Democratic Socialists of America's growing foothold in progressive media.
  • Uncomfortable Conversations with Josh Szeps

    JUST JOSH: The Unlearned Lesson of 9/11

    2026/09/10 | 2h 39 mins.
    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 marathon editorial, he reflects on the day itself, the complacency of the 1990s, the "clash of civilisations", popular misconceptions about al Qaeda's motivations, the extraordinary backstory of the Saudi royals and Osama bin Laden, and the moral conundrums of terrorism and war.
    Lastly, Josh offers the insight you need to take away from September 11th to avoid being blindsided by the civilisational challenges of today.
  • Uncomfortable Conversations with Josh Szeps

    Jewish Comedy at the Bondi Attack

    2026/09/07 | 1h 20 mins.
    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. Of course.
    David Rose found out his great-grandfather was a famous 19th-century caricature of the stereotypical "Hebrew comic", who performed with the Marx Brothers. Suddenly, David found that audiences expected him to account for Gaza.
    After the Bondi Beach terrorist attack, the newly Jewish (but still uncircumcised) David Rose staged a show at the Bondi Beach Pavilion entitled "Nepo Great Grandbaby", wrestling with the Jewish sense of humour before Nazism, after Nazism, before Gaza and after Gaza.
    Fresh from the Edinburgh Fringe Festival, he swung by the Uncomfortable Conversations studios to discuss the craft of comedy, terrorism, trigger warnings, Vaudeville jokes and anti-Jewish sentiment.
    David's show returns to Sydney and Melbourne next week. Get tickets at https://www.davidrosecomedy.com/
  • Uncomfortable Conversations with Josh Szeps

    Are Men Toxic?

    2026/09/03 | 26 mins.
    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, exactly? How do we explain and reduce male misbehaviour against women?
    Ben Vasiliou is the CEO of Australia's leading preventative mental health charity for teenage boys, The Man Cave. He joins Josh to discuss loneliness, identity, women’s rights activism, male relationships and the influence of the manosphere.
    Ben’s new book is “Better Man: Reclaiming masculinity for good”.
  • Uncomfortable Conversations with Josh Szeps

    What is Elon Up To?: An Idiot’s Guide to Space and Why You Need to Pay Attention

    2026/08/31 | 1h 53 mins.
    You may not realise it, but humankind is on the cusp of an extraordinary space race. Are we about to become a multi-planetary civilisation? Do we really need a super-fuel-tanker floating in space? Just how many A.I. data centres does Elon want floating high above your head?
    Anthony Colangelo is a proud space nerd who knows anything and everything about the latest state of play between SpaceX, Blue Origin, NASA and the Mars mission. He hosts two podcasts, Main Engine Cut Off and Off-Nominal, and he joins Josh for brain-tickling banter about why the space shuttle sucked, why satellite communication constellations like Starlink will become indispensable, and everything you need to know about the unfolding revolution in humanity’s adventures off the face of this planet.
More Comedy podcasts
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  
Podcast website

Listen to Uncomfortable Conversations with Josh Szeps, Podcast and Chill with MacG and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features
Uncomfortable Conversations with Josh Szeps: Podcasts in Family