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PODCAST

Old School with Shilo Brooks

Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. New episodes out every Thursday. Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks

arts books

All Episodes

41:14

The Lost Art of Taking the Piss with Richard Dawkins

Old School with Shilo Brooks ·

2025/12/18

Richard Dawkins is best known as a formidable evolutionary biologist and biting critic of religion. But when he wants a break from polemics and proofs, he turns to P.G. Wodehouse for a belly laugh. Wodehouse’s satire skewered British aristocrats, Hollywood phonies, and self-important moralists with surgical precision. In this episode, Shilo Brooks sits down with Dawkins to find out why the British humorist remains one of the sharpest writers in the English language. The conversation ranges from

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64:35

Living Through the Fall of a Regime

Old School with Shilo Brooks ·

2025/12/11

“If we want things to stay as they are, things will have to change.” This famous line from The Leopard has become a shorthand for moments when a ruling order senses its own looming downfall. And it feels eerily relevant now, in an age when the liberal order we cherish seems increasingly unsteady. We are living in a moment when we shout “regime decline” from the rooftops. Giuseppe Tomasi di Lampedusa’s classic novel is about what it feels like to live inside history—inside the collapse of a social

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62:39

Read This Book Instead of ‘The Catcher in the Rye’

Old School with Shilo Brooks ·

2025/12/04

According to Ryan Holiday, Walker Percy’s The Moviegoer is like the better, more mature cousin to The Catcher in the Rye. In this episode, Shilo Brooks sits down with the author and Daily Stoic founder to discuss the quiet Southern novel set in postwar New Orleans. The book follows a Korean War veteran who has money, women, and a respectable job but whose inner life is defined by existential malaise and a spiritual itch that he calls “the search.” In the end, he resigns himself to the humdrum

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63:12

George Orwell’s Lessons on the Class Divide

Old School with Shilo Brooks ·

2025/11/20

Most of us have read 1984 or Animal Farm. But fewer know of George Orwell’s first great work—an unvarnished account of his descent into the world of society’s outcasts. In this episode of Old School, Shilo Brooks sits down with Rob Henderson to discuss Down and Out in Paris and London, which is inspired by Orwell’s real-life plunge into the slums of two great European cities.Henderson draws on his own trajectory from foster care and poverty to the rarefied worlds of Yale, Cambridge, and elite

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61:54

What ‘The Great Gatsby’ Taught Fareed Zakaria About...

Old School with Shilo Brooks ·

2025/11/13

It’s been 100 years since The Great Gatsby was published. In this episode, Shilo Brooks sits down with journalist Fareed Zakaria to explore why the F. Scott Fitzgerald novel still feels so modern. Zakaria shares his experience discovering the classic as an Indian immigrant, describing Gatsby as his gateway to understanding America. Together, they unpack the book’s enduring themes: the allure of reinvention and the American dream, the search for meaning in a world stripped of faith and tradition,

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60:44

How Thomas Sowell Transformed Coleman Hughes

Old School with Shilo Brooks ·

2025/11/05

Why do we believe what we believe? And how do those beliefs shape our politics? Thomas Sowell, one of the world’s most influential economists and social philosophers, set out to answer this question in his 1987 book, A Conflict of Visions. In it, he traces the underlying logic behind all modern political divides—why it is that knowing someone’s position on one issue, say gun control, makes it easy to predict their position on a totally unrelated issue, like abortion. In this episode, Shilo

en

57:42

Nick Cave on ‘The Adventures of Pinocchio’

Old School with Shilo Brooks ·

2025/10/30

Carlo Collodi’s The Adventures of Pinocchio is a dark, dazzling Italian fable that is worlds apart from Disney’s sanitized version. Beneath its fantasticism and humor, the story is brimming with poverty, violence, and existential peril. In this episode, Australian rock legend Nick Cave joins Shilo Brooks to talk about one of the best-selling and most widely translated books ever written. Together, they explore how transgression and disobedience shape character and how art thrives in defiance of

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54:51

Why We Still Need Plato

Old School with Shilo Brooks ·

2025/10/23

What is justice? And why should we live justly? These questions lie at the heart of Plato’s Republic, the foundational text of Western philosophy. In building his utopian city, Plato reveals how the quest for perfect justice can slip into tyranny. Yet his call for relentless self-examination—for resisting nihilism and seeking meaning—remains a starting point for us all.In this episode, Dr. Cornel West joins Shilo Brooks to discuss why ancient Greek philosophy remains relevant for all of us,

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67:31

What Steven Pinker Taught this Pro Bodybuilder about...

Old School with Shilo Brooks ·

2025/10/16

Dr. Mike Israetel is a bodybuilder and scientist who believes reading is as important as a gym session. Steven Pinker’s The Blank Slate changed his life. In this episode, Israetel joins Shilo Brooks to discuss how this explosive book on genetics, human nature, and the myth of infinite potential turned his own outlook (and coaching style) upside down, inspiring humility, killing illusions, and sharpening his science-first approach to diet and training. And he explains why athletes need to stop

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68:01

MeatEater’s Steven Rinella on Lessons from the...

Old School with Shilo Brooks ·

2025/10/09

Few people have turned a love of the wild into a cultural force quite like Steve Rinella, the outdoorsman and author behind the MeatEater empire. Jim Harrison’s Wolf, published in 1971, changed Rinella’s life. In this episode, Rinella sits down with Shilo Brooks to discuss this stream-of-consciousness novel replete with chaos and male angst. He reflects on growing up in rural Michigan and seeing himself in Harrison’s protagonist—a bitter, damaged, self-destructive young man on a quest for meaning in

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59:29

The Old Man and the Sea with Admiral James Stavridis

Old School with Shilo Brooks ·

2025/10/09

Admiral James Stavridis once commanded fleets as Supreme Allied Commander of NATO. Now he commands a collection of 5,000 rare books. Ernest Hemingway’s The Old Man and the Sea changed Stavridis’ life. In this episode, the admiral sits down with Shilo Brooks to discuss the themes of hardship, pride, and resilience that appear in Santiago’s epic struggle at sea. Stavridis, who stuck out in the military for his love of books, and stuck out as a law school dean for his love of the military, explains how

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0:57

Introducing: Old School with Shilo Brooks

Old School with Shilo Brooks ·

2025/09/22

Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. Coming October 9th. Learn more about your ad choices. Visit megaphone.fm/adchoices

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