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Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
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444 episodes

  • Uncomfortable Conversations with Josh Szeps

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

    2026/04/08 | 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

    2026/04/07 | 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

    2026/04/05 | 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.
  • Uncomfortable Conversations with Josh Szeps

    A Black Muslim Comic & Gay Jew Walk Into an Uncomfortable Conversation

    2026/04/03 | 1h 3 mins.
    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’
  • Uncomfortable Conversations with Josh Szeps

    Nazi Jokes & Stand-Up Taboos with Tom Ballard

    2026/04/01 | 1h 19 mins.
    Think of Tom Ballard as a young John Oliver, who hosted Australia's national nightly satirical news television show ,"Tonightly with Tom Ballard".

    He returns to the show to discuss his getting cancelled for doing a Nazi salute, punching down, anti-semitism, Gaza & Zionism, cancel culture and offensive comedy.

    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.

    Ballard's stand-up show is ‘Be Funny Challenge (Impossible)’ and his play about stand-up and cancel culture is ‘JKS: a Comedy(?)’

    Tickets at comedyfestival.com.au

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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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