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 culture. Their conversation examines why people with privilege so often misunderstand the realities of the poor, how poverty shapes the mind and spirit, and what Orwell ultimately discovered about the divisions—and the common ground—between classes.
Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.
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Learn more about your ad choices. Visit megaphone.fm/adchoices
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What ‘The Great Gatsby’ Taught Fareed Zakaria About America
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, and the spiritual hollowness that accompanies wealth and glamor. They also discuss Fitzgerald’s unique partnership with his editor Maxwell Perkins, a writer-editor collaboration that helped transform Gatsby into one of the greatest works of American literature. Plus: Zakaria sounds off on what’s wrong with journalism—and its consumers—today.
Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.
Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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How Thomas Sowell Transformed Coleman Hughes
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 Brooks sits down with Coleman Hughes to discuss the book that Sowell himself calls his favorite. Their conversation—recorded well before yesterday’s election of Democratic socialist Zohran Mamdani—illuminates why some of us buy into utopian projects of remaking society, while others trust the quiet power of incentive structures like free markets.
Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.
Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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Nick Cave on ‘The Adventures of Pinocchio’
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 conformity. Cave reflects on how the story helped him process grief after the death of his son. In examining the puppet’s journey to becoming a real boy, Cave and Brooks consider how love and suffering make all of us real.
Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.
Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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Why We Still Need Plato
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, regardless of race or background. Together, they argue that confronting Plato is a universal rite of passage for everyone seeking to overcome despair and live a good life. Plus: West critiques the corruption of American universities and political parties—especially the Democratic Party, which he declares “beyond redemption.”
Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.
Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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
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