He’s a one-man wellness, publishing and podcasting empire. Rich Roll started getting fit in middle age and is now a world-renowned vegan ultra-endurance athlete.

Dick Cavett is one of the greatest television talk show hosts of all time. After being a writer on the original NBC Tonight Show (first with Jack Parr, then with Johnny Carson), Cavett got his own show in 1968. It ran for nearly 40 years and cemented him as a titan of American broadcasting, hosting seminal political debates as well as Hollywood’s biggest stars. A few years ago, Cavett appeared on Josh’s TV show. This is the audio of that encounter.

“The Mooch” was a wildly successful investment banker when he joined Donald Trump’s presidential campaign. He became the White House Communications Director in 2017. Anthony tells Josh about his time in the White House, his relationship with Trump, and what kind of a guy he really is. 

Josh is backpacking around West Africa. As you do. What’s it like? He’s here to tell you, recorded live from the road (or the dusty track, as the case may be). Sign up below on our FREE Substack tier to hear the whole thing. https://uncomfortableconversations.substack.com/subscribe

Universities are now dominated by diversity, equity and inclusion mandates, says the philosopher Peter Boghossian… and the result is a stultifying climate of intellectual conformism. In this all-new instalment of Permission to Think, our collaboration with the UTS Faculty of Arts and Social Sciences, Josh and Peter debate how universities, and our culture at large, can reclaim true intellectual freedom.

If you're a greenie, you're supposed to be anti-nuclear. That was true of the former Extinction Rebellion spokesperson Zion Lights... until she became one of Britain's most prominent advocates for nuclear power. But do her claims stand up to Josh's scrutiny?

Josh walked into a bar in Brooklyn and, in front of a packed crowd of drunks, argued about the news with some of the funniest, smartest people in New York. This is that event.

Jamie Kirchick knows everything about the secret, spooky, saucy, seedy side of Washington DC. Hear him hold forth on the secret history of gay spies, trans activists and, of course, the never-not-impending arrest of Donald J Trump.To hear the full episode for FREE, sign up to the free tier on Josh's Substack at: https://uncomfortableconversations.substack.com/subscribe

In this brand new venture, Josh addresses some of life's deepest questions as posed by his friend and work colleague Robbie Armfield. In this first episode, Robbie has anxiety about generating sounds and aromas in the office toilet cubicle. Robbie has questions. Josh has the answers.  You can find more from Robbie on his podcasts "Welcome to Meet You" and "Robbie's Modern Life".

The brilliant Coleman Hughes is an American writer, podcaster and musician. He burst onto the intellectual scene at a young age with his ruthlessly well-articulated opinions on race and public policy issues. He joins Josh this week with his giga-brained thoughts on race, equity and inclusion. 

You probably know Zach Cregger from comedy shows like Wrecked and Whitest Kids U'Know. He also wrote and directed Barbarian, one of the horror films of 2022. This chat from the #WeThePeople LIVE archive is a conversation Josh and Zach had in Puerto Rico in 2016 where they spoke about the process of making good comedy, procrastination and how social media kills creativity. 

For most transgender people, transitioning is one of the greatest experiences of their lives. For others, it deforms into crippling regret. KC Miller is one of them.

Dr Ball is a scientific futurist whose book is Converge: A futurist's insights into the potential of our world as technology and humanity collide." She and Josh wrestle with artificial intelligence, the future of food, radical life extension, and air fryers.

Tim Urban’s first appearance on this show remains one of the all-time favourites. Now, this explosive thinker of cosmic, civilisation-level thoughts returns with a book: “What's Our Problem? A Self-Help Book for Societies”. He and Josh wrestle with what’s going wrong. Why is everything a mess? Why is everyone acting like a baby? When did things get so tribal? Why do humans do this stuff? Hosted on Acast. See acast.com/privacy for more information.

From the #WeThePeople LIVE archives this week to a 2016 chat with the wonderful Myq Caplan. First and foremost Myq is comedian. Josh and Myq chat about what funny is, how he became funny, and the creative process he uses to stay funny. Enjoy.For the full episode sign up at uncomfortableconversations.substack.com Hosted on Acast. See acast.com/privacy for more information.

Susan Neiman is one of the world's most respected living philosophers. She was born in America and educated at Harvard but now lives in Germany, where she's the director of the Einstein Forum and a member of the Berlin-Brandenburg Academy of Sciences. She's a leading expert on the Enlightenment. Her new book is Left is not Woke. Hosted on Acast. See acast.com/privacy for more information.

This week, the world's biggest LGBTQI+ event, World Pride, kicks off in Sydney. Right on cue, activists are calling to boycott a new Harry Potter video game because Rowling is a famous anti-trans bigot. But... is she? Hosted on Acast. See acast.com/privacy for more information.

The so-called "intellectual dark web" was supposed to shine a light on issues too thorny for the mainstream media to touch. Now, it's a basket case of kooks. The journalist Ross Anderson recently wrote an amazing feature on the "red-pilling" of the gay conservative online host Dave Rubin. He's here to explain what's going wrong.  Hosted on Acast. See acast.com/privacy for more information.

Josh gets excited, at long last, about a realistic plan for fighting climate change while creating new jobs and a healthier environment. In short: electrify everything. For more about Saul, check out his website HERE.Subscribe to our Substack HERE. Hosted on Acast. See acast.com/privacy for more information.

Going back some five years to Josh's first ever chat with the now Uncomfy Convos regular, the self-help psychology sage Oliver Burkeman. On this episode we talk about happiness, drawing on his 2012 book The Antidote: Happiness for People Who Can't Stand Positive Thinking. Hosted on Acast. See acast.com/privacy for more information.

Helen Lewis's new BBC Radio 4 show, The New Gurus, investigates why so many of us have turned away from mainstream medicine, mainstream politics and the mainstream media to embrace the power of charismatic individuals instead. Helen went viral in 2018 with her legendary interview with Jordan Peterson. She's a brilliant interrogator and a thoughtful critic of the culture wars, wokeness, gender ideology and the far right. Hosted on Acast. See acast.com/privacy for more information.

This week Josh reflects, in a somewhat heated way, on the surreal injustices of the justice system. Plus: Aussie-made shoulder-launched drone guns. And sharks in Sydney harbour. Hosted on Acast. See acast.com/privacy for more information.

Sam Harris is a best-selling writer, philosopher and neuroscientist who hosts one of the world's most influential intellectual podcasts, Making Sense. Josh wants to pin down, once and for all, Sam's feelings about his former associates in the "intellectual dark web" who've gone off the rails. They also discuss Elon, Twitter, and the best flavour of cookie.To subscribe to the premium podcast feed via substack head to: https://uncomfortableconversations.substack.com/subscribe Hosted on Acast. See acast.com/privacy for more information.

Scott Adams is the creator of the cartoon strip Dilbert. He rose to Twitter prominence ahead of the 2016 US election where he picked Trump as the winner, praising him as a master persuader. We leave Trump aside in this episode and focus on Scott's advice on creativity and success that he details in his 2014 book - How to Fail at Almost Everything and Still Win Big. Hosted on Acast. See acast.com/privacy for more information.

For this last Best Of episode we have the amazing Kurt Fearnley - paralympian, media personalist and advocate, who brings an amazing perspective on the global experience of disability. Then, the show I get the most feedback on, my diatribe about gun laws. And finally, one of the world’s foremost experts on sex differences - the historian and bioethicist Alice Dreger. Hosted on Acast. See acast.com/privacy for more information.

This week, Josh airs what's on his mind. Did the NFL star Damar Hamlin suffer cardiac arrest because he was vaccinated, or because he was smashed in the chest by six-foot-four, 220-pound receiver? Was the musical editor of The Simpsons, who died this week, the greatest TV composer of all time? We revisit the best-ever Simpsons songs to find out! Is there anything redeeming about seagulls? And as we learn new facts about the Buckingham Palace racism scandal, Josh finds himself confused... Is it always racist to ask where you're from? Hosted on Acast. See acast.com/privacy for more information.

The holiday interlude continues with our top podcast moments. Andrew Denton is a giant of Australian media. Now out of the limelight, he focuses much of his work on voluntary assisted dying advocacy. Tim Flannery - ecologist, explorer, and Australian of the Year winner brings us an amazing perspective on what it is to understand nature, and humanity’s place within it. And finally Ana Marie Cox - one of the most uncomfortable conversations of the last year. We argue about cancel culture from the left and from the right. Do we meet in the middle? Listen to find out. Sign up for free at our Substack to get the full show: https://uncomfortableconversations.substack.com/subscribe Hosted on Acast. See acast.com/privacy for more information.

Well what a year it has been! And as we end every year here on Uncomfortable Conversations, it’s time for me to answer your questions. What have you been noodling on in 2022? And what do I reckon about it all? It’s time to find out.   Hosted on Acast. See acast.com/privacy for more information.

It's time for a Christmas interlude, the best parts of our favourite uncomfortable conversations. Tim Urban is still probably my all-time favourite guest. The creative genius behind the blog Wait But Why brings his brain melting takes on the world, and our place within it. Clementine Ford and I have some disagreements. Neither of us pull a punch. Our chat gets to the heart of what we’re trying to do here. And Malcolm Turnbull, Australia’s 29th Prime Minister. What an opportunity it was to quiz an ex PM about his views on the current political climate, his time as leader, and the chaos that led to his eventual downfall. Enjoy! Hosted on Acast. See acast.com/privacy for more information.

The Guardian has called Rutger Bregman "the Dutch wunderkind of new ideas". He has a forward thinking, earnest approach to the small task of making the world a better place for everyone - something he's been working on this since his early 20's. This episode is taken from the #WeThePeople LIVE archive.To get the full episode go to www.uncomfortableconversations.substack.com/listen Hosted on Acast. See acast.com/privacy for more information.

Eric runs the investment firm of the right-wing multi-billionaire Peter Thiel, the co-founder of PayPal and the first outside investor in Facebook. Yet Eric is a left-wing political dissenter. With a PhD in mathematical physics from Harvard, he’s a confounding genius. He coined the term “the intellectual dark web”. His journey is perplexing. His vision of the future is ominous. Join Josh on his journey down the Weinstein rabbit hole. Hosted on Acast. See acast.com/privacy for more information.

On this special episode from Josh's archive, he speaks with legendary British documentarian Louis Theroux. For decades, Louis has thrust himself into strange and extreme worlds, casting a light on the fringes of the human experience. This interview took place at the time of the release of his first feature film: My Scientology Movie. Hosted on Acast. See acast.com/privacy for more information.

Bridget is a podcasting and publishing phenomenon. She and Josh discuss everything from Peruvian ayahuasca ceremonies, to Joe Rogan, to cancel culture, to the Byron Bay cult she momentarily joined. Oh, and how motherhood has made her finally appreciate Christmas. Hosted on Acast. See acast.com/privacy for more information.

Tom Ballard is one of Australia's most successful comedians. He may be the millennials’ most prominent, hilarious voice of fury against capitalism and boomers. Tom and Josh argue about the benefits and perils of 21st-century capitalism, free speech and liberalism.  Hosted on Acast. See acast.com/privacy for more information.

We're launching a new Uncomfortable Conversations community. Get loads more content for free! This is the most important thing you'll hear this month. Don't miss it. Hosted on Acast. See acast.com/privacy for more information.

Kat is a feminist who takes no bullshit. She created a stir with her piece “Why I Keep Getting Mistaken for a Conservative”. She and Josh discuss the challenges faced by women and the fallout of the #metoo movement. Hosted on Acast. See acast.com/privacy for more information.

James Lindsay is one of the most controversial figures on the American right. He was permanently banned from Twitter in August, until Elon reinstated him this week. He initially gained famed debunking the social-justice left. Since then, he has become notorious for increasingly dire warnings about an authoritarian leftist takeover of culture. Is he a crank, or a genius? Josh tries to figure him out.   Hosted on Acast. See acast.com/privacy for more information.

When you see the colour blue, is it the same as when I see the colour blue? How does your brain create an image of the world... and of yourself? Dive into the wild world of the matrix with one of the world's leading neuroscientists, Anil Seth. His bestselling book is Being You: A New Science of Consciousness.   Hosted on Acast. See acast.com/privacy for more information.

Josh is being eviscerated on social media for spreading pro-vaccine misinformation. Did he? What did he, and we, get wrong about Covid? Hosted on Acast. See acast.com/privacy for more information.

How do you stitch together diverse immigrant societies into a common future? How do you avoid collapsing into quarrelling tribes? Yascha Mounk is an optimistic academic who understands how democracies thrive... and decay. Hosted on Acast. See acast.com/privacy for more information.

Josh reflects on Elon Musk, Kanye, Israel, and the rise of online Jew-hate. Hosted on Acast. See acast.com/privacy for more information.

What will Elon Musk do with Twitter? Who wants to live inside Mark Zuckerberg's Metaverse? Should Facebook censor hate speech? Jordan Guiao lived and worked in Silicon Valley and he knows big tech inside and out. We was formerly a digital strategist and the head of social media for the ABC and SBS respectively, and is currently a Research Fellow at The Australia Institute’s Centre for Responsible Technology. His new book is Disconnect - Why We Get Pushed to Extremes Online and How to Stop It. Hosted on Acast. See acast.com/privacy for more information.

Josh reflects on Kanye's antisemitic meltdown, Taylor Swift's supposed fat shaming video and activism in Iran. Hosted on Acast. See acast.com/privacy for more information.

David got his PhD in political thought from the London School of Economics and now teaches at King’s College London. He was a political science lecturer at the National University of Singapore and an associate editor of the University of Malaya’s South East Asian Studies journal. He explains the echoes he sees in the West of Mao's Cultural Revolution. A politics of rage. Intellectual conformism. Cancel culture. This episode is a collaboration with the University of Technology Sydney as part of its "Permission to Think" series.  Hosted on Acast. See acast.com/privacy for more information.

Emile is the Academy Award-winning producer of Lion, The King’s Speech, Rabbit-Proof Fence and The Power of the Dog. His cousin is a high-flying corporate consultant and former anti-apartheid activist. They have a podcast, Principle of Charity, which seeks to find common ground between opponents on controversial issues. But how far can talk take us, really? Don’t miss this electrifying debate. Hosted on Acast. See acast.com/privacy for more information.

Should women aspire to the same things as men? Or have they been betrayed? Louise says we lie to young women about who they are and what they should want. She's a journalist, anthropologist, activist and the writer of the new book "The Case Against the Sexual Revolution". Hosted on Acast. See acast.com/privacy for more information.

On the previous episode of Uncomfortable Conversations, the trans activist Dianna Anderson alleged bad journalism by Jesse Singal, who wrote the bombshell 2018 Atlantic magazine piece, "When Children Say They're Trans". Josh left the issue dangling, agreeing that it deserved a fact-check. Don't listen to this episode until you've heard Dianna's. Here, Jesse responds. Hosted on Acast. See acast.com/privacy for more information.

Dianna E. Anderson is a gender non-binary writer and activist whose latest book is “In Transit: Being Non-Binary in a World of Dichotomies”. They and Josh disagree on a lot: the reality of biological sex, journalists who criticise trans issues, and whether burqas are sexist. Here, they hash it all out. Hosted on Acast. See acast.com/privacy for more information.