Uncomfortable Conversations with Josh Szeps

Comedy Kingmaker on Speaking Fearlessly & Living Well

Noam Dworman is the owner of comedy’s most revered venue, the Comedy Cellar, sometimes referred to as the "Harvard” of comedy clubs. He transformed it from a single 1980s room in Greenwich Village into a five-venue behemoth. The stars who made their name on Dworman’s stage are a who’s who: Richard Pryor, Steve Martin, Chris Rock, Jon Stewart, Amy Schumer, Ray Romano, Sarah Silverman, Dave Chappelle, Louis C.K. Why does Noam still do it? What has he learned about how to lead a good life? Is it harder to get ahead as a small business owner these days? And why is he getting fined for other people’s sidewalk trash? Josh visits Noam at his studio above the Cellar to discuss how to give the benefit of the doubt to people who are wrong—from border-town voters, to Trump officials. They wrestle with free speech, ICE, bureaucracy, and why cancel culture’s “consequences” might be harsher than we think.

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What Israeli Election?

As we hold our breath to find out whether Israelis will finally spurn Netanyahuism, Yael Bar Tur joins Josh to definitely NOT discuss the Israeli election. Yael majored in counterterrorism in Israel and has a master’s in public policy from the Harvard Kennedy School of Government. As the NYPD’s head of digital, she was on the front lines of the official response to the defund-the-police movement of the 2010s. Josh and Yael dug into the Israeli electoral system, the American banking system, policing, and, randomly but inevitably, the new documentary about Elizabeth Holmes.

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Stephen Fry on Love, Trump and Learning Not to Care

This episode is part of The Best Of series and was originally posted in 2024. Few Britons are as iconic as Stephen Fry. On TV, he’s an Emmy-winning comedy legend immortalised in shows like A Bit of Fry & Laurie, Jeeves & Wooster, and Blackadder. He has hosted the British Academy Film Awards twelve times and won six BAFTAs as the host of the smash-hit BBC television quiz show Q.I. On stage, Stephen’s adaptation of Me and My Girl won two Olivier Awards. He was nominated for a Tony for his performance in The Globe’s production of Twelfth Night on Broadway. On the big screen, he’s starred in Wilde (as Oscar Wilde, a performance nominated for a Golden Globe), Gosford Park, Chariots of Fire, A Fish Called Wanda, V for Vendetta and The Hobbit. Stephen is the voice of all the Harry Potter audiobooks. His eloquence infuses his countless essays, comedy sketches, articles, novels, and books about Greek mythology. His autobiography, Moab is My Washpot, with its raw honesty about his screwed-up teenage years, was transformational for a young Josh Szeps. On a trip to Sydney, Stephen swung by the Uncomfortable Conversations studios to visit with Josh. Enjoy this sparkling conversation about the cycle of life, the richness of being human, finding creative authenticity, and ignoring Donald Trump.

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Midterms! France! Josh is in DC! Yayyy

Is the exhausted majority stuck choosing between two extremes that can’t be satisfied, and what happens when the far left and far right go head to head? Josh chats with comedy writer and author of I Might Be Wrong, Jeff Maurer, live from a Washington, DC, hotel room, about why centrists keep losing the argument on both sides. They dig into the chaos in France, where a nation that riots over a modest rise in the retirement age may now face a runoff between an old-school communist and Marine Le Pen, and why Jeff thinks the far right wins that contest almost every time. They also cover the motte-and-bailey fallacy, Australia’s superannuation fix versus America’s looming Social Security cliff, why the left needs its own “Nixon goes to China” moment, the illiberal turn in progressive race politics, and the case for a really basic version of Medicare for All.

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BREAKING: A Note on Political Violence

Is it more ethical to prosecute your moral beliefs, or to understand people who disagree? Who, exactly, is fomenting polarisation? Who is capable, potentially, of political violence? Is it, perhaps, all of us? Especially those of us convinced we’re doing good? Several months ago, Josh hosted an Uncomfortable Conversations panel event at a black-tie gala in the nation’s capital with the federal member of parliament Helen Haines. This week, Haines was intentionally rammed by a car. She has lost both her legs. The prime minister is trying to soothe a shocked nation by encouraging “people in positions [of influence]… to join in the call to turn [the] temperature down.” Josh knows a thing or two about fostering conversations across ideological divides. In this ad-libbed editorial from New York, Josh argues that telling other people to turn the temperature down is worse than useless. Nobody thinks their own temperature is set too high. Rather, we believe that less passionate people are feckless or corrupt. This points a way forward, towards how we all might participate in creating a more cohesive society. Our thoughts are with Helen, her family and her loved ones. We hope that in some tiny way, this helps.

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"Why are you here?" with Tim Urban

This episode is part of The Best Of series and was originally posted in 2021. Tim Urban’s first appearance on this show remains one of my all-time favourites. Why are you here? Are we alone in the universe? Will we extinguish ourselves? Why do you procrastinate? And what does social media reveal about your chimpanzee mind? Tens of millions of viewers watch philosopher-blogger king Tim Urban wrestle with these questions in TED Talks and on his comic blog, 'Wait But Why'. Spark up a reefer and join Josh on a cosmic journey into a genius mind.

How my upbringing shaped my world view with Josh Szeps

This episode is from the You’re A Good Kid podcast, featuring your humble host, Josh Szeps. This is a candid look into the life and mind of a boy who grew up in Sydney's inner suburbs and how love, family, and creativity shaped his strong self-confidence. This episode was originally published on the You’re A Good Kid podcast in July 2026.

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How A.I. is "Demolishing" Mathematics

A.I. is unleashing a “judgment day” on everything from algebra and geometry to probability and logic. What happens to human knowledge when it's dropped in our laps instead of being understood? It was just days ago that OpenAI dumped 722 new mathematics papers online, claiming extraordinary mathematical breakthroughs. Professional mathematicians are stupefied. Many of them are worried that A.I. risks prematurely shutting down lines of inquiry. Will humans receive ready-made insights with no new techniques, questions or, ultimately, understanding? One leading mathematician even needed to use A.I. to read the A.I.’s proof of the problem she spent years working on. Adam Spencer is a mathematics communicator and broadcaster whose Substack, NerdNews, discusses math, A.I. and general geekiness. He joins Josh to describe the shockwaves in the field and to wrestle with the pros and cons of super-intelligent machines solving humankind's deepest questions for us. Read Adam Spencer’s Substack https://adambspencer.substack.com/

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Consent and the "Cornell 7"

A female university student visits a male frat house at night. She is drugged and raped, for seven hours, by seven male students. She reports it but the university authorities sweep it under the rug. No charges are laid. That's the story that has lit up the media and sparked thousands of online arguments since the young woman filed a 101-page civil complaint. She names seven of the young men and seven organisations, including Cornell University itself. Seven rapists, seven hours, seven organisations. Yesterday, Cornell students occupied a dining hall on campus in solidarity... for seven hours. The district attorney reopened the case. The state governor appointed a special prosecutor. A special committee was set up. A review was launched. The university's president says this is a turning point in Cornell’s history. Students are calling for his resignation. The story depicted above, though, of being drugged and gang raped, is not the accuser's own account of what happened. It's folklore being repeated by politicians, activists, celebrities and commentators. The woman's own story is more subtle, more intriguing, and more challenging. Kat Rosenfield is a culture writer and podcaster on Substack and for the Free Press. She's an unflinching analyst of female sexuality, male violence, justice, and consent. Kat takes Josh to the heart of the profound but uncomfortable questions that usually make conversations about male violence and female safety so fraught.

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JUST JOSH: Conspiracies & FlyDubai, Oh My

When does healthy scepticism become unhinged suspicion? How do you know if you’re being gullible or sensible? What are the cognitive traps that social media pulls us into? And why should you care? As soon as news broke of a violent attack in the cockpit of a FlyDubai 737 en route to Tel Aviv, the internet pushed back. Something was fishy. There were anomalies in the official story. Viral videos from both the left and the right hinted at an Israeli plot. Josh is on vacation, but he interrupted his important work reviewing Texas rodeos to bring you this emergency livestream. He reflects on the difference between clear thinking and muddled thinking about uncertain events. Using Carl Sagan, The Simpsons and The Protocols of the Elders of Zion, he presents the FlyDubai incident as a lesson in how to protect the most valuable asset you own — your rationality.

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Why do smart people believe stupid things?

Every human mind is a propaganda machine. It manufactures certainty, reinforces old narratives, and keeps us loyal to beliefs that no longer serve us. In an era of infinite information and AI-generated content, these internal distortions make it tricky to distinguish between insights and self-bullshit. Owen Fitzpatrick is a social psychologist who's travelled to more than 100 countries and studied propaganda first-hand in places like North Korea, Rwanda, and Afghanistan. He now sees it operating insidiously at home, as well. Owen joins Josh to discuss his new book "Inner Propaganda: Leading Hearts and Minds Through Turbulent Times". They wrestle with dictatorships, a free media, misinformation, echo chambers, polarisation, fragmentation... and how understanding our own stories can help us bridge divides, rather than deepen them.

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Free speech, hate speech, and the limits of Liberal tolerance with Sami Shah

What do we actually owe each other in a society trying to hold pluralism, free speech, and real religious and ethnic tension together at the same time? Josh sits down with comedian, writer, and Crikey columnist Sami Shah, born Muslim in Pakistan, where his satirical writing on religious extremism drew death threats and a fatwa before he found his way to Australia. They cover an extraordinary amount of ground: the strange mirror-image psychology of ex-Muslims who drift right and anti-Zionist Jews who drift left, the conditional condolences that followed the Bondi terrorist attack, whether the Anti-Semitism Royal Commission was ever built to answer the question it was created for, and the big philosophical difference between America's individual-rights conception of free speech and Australia's more communitarian one.

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Who's hacking you right now? with ethical hacker Assadi Youssef

When you read news about a data breach which might have exposed your information, do you even care? Who’s behind all this hacking: China, Russia, or a nerd in his parents’ basement? Are our water and electrical systems at risk? And is A.I. going to make things more secure, or will it destroy privacy altogether? Assadi Youssef got into computer hacking as an eleven-year-old boy before becoming an “ethical hacker”, meaning he’d find vulnerabilities in supposedly impenetrable systems. He’s now an online security genius, advising banks and critical infrastructure companies on how to protect their systems from catastrophic attack. He joins Josh to explore who’s doing all this hacking, whether you need a universal digital I.D, how A.I is changing the game, and whether you really even need two-factor authentication, after all.

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William Shatner Doesn’t Want to Die, from The Moynihan Report

Today we’re sharing a bonus episode from The Moynihan Report. William Shatner sits down with Michael Moynihan in Los Angeles for a conversation about life, time, and knowledge. They talk about death, God, AI, Blue Origin, The Intruder, and the relentless curiosity that keeps Shatner looking for whatever comes next. Oh yeah, and at 95 years old, he’s releasing a heavy metal album.

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Social media broke our ability to agree, with Jonathan Haidt

Jonathan Haidt is considered one of the world's most influential living psychologists. He joins Josh on this new instalment of Permission To Think - a collaboration with The University of Technology Sydney School of Social Sciences. This episode is part of The Best Of series and was originally posted on 20th April, 2026. At the time of recording, Jonathan penned a piece for The Atlantic titled ‘Why The Past Ten Years Of American Life Have Been Uniquely Stupid’ that looks at how social media erodes trust, shared narrative and social capital.

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“So… *Does* God Hate F*gs?” with Megan Phelps-Roper

What do our modern-day culture wars have to teach us about cult-like thinking, moral puritanism, judgment and compassion? And if you lose religious faith, how are you left thinking about agnosticism, atheism, the purpose of the cosmos, and the meaning of life? What, if anything, is worth keeping from the Bible? Megan Phelps-Roper was raised in the Westboro Baptist Church, the fundamentalist cult that picketed soldiers’ funerals with placards saying “God Hates Fags”. She appeared in Louis Theroux’s documentary about the church, as its spokesperson and the granddaughter of its founder. Megan left the church, lost her family and her faith. Her TED Talk about polarization was viewed tens of millions of times. She hosted a smash-hit audio documentary series, The Witch Trials of J.K. Rowling, about the moral righteousness on both sides of the transgender debate. Her latest production is Book Keeper, a podcast about returning to the Bible, as an atheist, to figure out what stories are worth keeping. You can listen to Megan’s first appearance on this show here (https://uncomfortableconversations.substack.com/p/the-witch-trials-of-jk-rowling-with). She returns now to discuss atheism, the internal logic of religion, tribal thinking, social media and the way out of our self-certain culture-war bubbles.

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Is there any Room left for moderates? With Jeff Maurer

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.

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JUST JOSH: The Unlearned Lesson of 9/11

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.

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Jewish Comedy at the Bondi Attack

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/

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Are Men Toxic?

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”.

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