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Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
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446 episodes

  • Uncomfortable Conversations with Josh Szeps

    "Nuremberg" & the Psychology of Evil

    13/04/2026 | 1h 15 mins.
    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.
  • Uncomfortable Conversations with Josh Szeps

    Writing for 'SNL' with Sam Jay

    09/04/2026 | 37 mins.
    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.
  • Uncomfortable Conversations with Josh Szeps

    BREAKING: Trump Always Chickens Out (Thank F*ck)

    08/04/2026 | 55 mins.
    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.
  • Uncomfortable Conversations with Josh Szeps

    Dave Hughes Has a Problem With Josh

    07/04/2026 | 1h 20 mins.
    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.
  • Uncomfortable Conversations with Josh Szeps

    The King of Late Night TV, Steve Vizard

    05/04/2026 | 44 mins.
    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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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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