

Old School with Shilo Brooks
The Free Press
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
Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks
Episodes
Mentioned books

46 snips
Nov 20, 2025 • 1h 3min
George Orwell’s Lessons on the Class Divide
Rob Henderson, bestselling author of *Troubled* and a commentator on social mobility, joins to discuss George Orwell's *Down and Out in Paris and London*. Their discussion reveals how Orwell's experiences with poverty illustrate class divides and misunderstandings between the privileged and the poor. Henderson shares insights from his own life in foster care, contrasting it with elite culture and addressing the subjective nature of poverty. They touch on the challenges of self-sabotage, modern homelessness, and Orwell's sharp humor, making for a fascinating exploration of social class.

18 snips
Nov 13, 2025 • 1h 2min
What ‘The Great Gatsby’ Taught Fareed Zakaria About America
Fareed Zakaria, a renowned journalist and political commentator, discusses the impact of 'The Great Gatsby' on American culture and his personal journey as an Indian immigrant. He describes the novel as a lens for understanding America's allure of reinvention and the American dream. They dive deep into themes of wealth, moral ambiguity, and the spiritual hollowness that accompanies success. Zakaria also critiques modern journalism, lamenting the shift towards quick, sensational content over in-depth analysis.

102 snips
Nov 5, 2025 • 1h 1min
How Thomas Sowell Transformed Coleman Hughes
In this conversation, Coleman Hughes, an insightful author and commentator on race and culture, shares how Thomas Sowell's seminal work transformed his understanding of societal issues. Coleman unveils Sowell's idea that group disparities stem from various factors beyond racism. He contrasts constrained and unconstrained views on human nature, emphasizing the importance of real-world incentives over idealistic approaches. Their discussion dives into the complexity of political beliefs, the nature of power, and the pragmatic lessons from Sowell's insights.

11 snips
Oct 30, 2025 • 58min
Nick Cave on ‘The Adventures of Pinocchio’
Nick Cave, the iconic Australian singer-songwriter and frontman of Nick Cave and the Bad Seeds, joins the conversation to delve into Carlo Collodi’s *The Adventures of Pinocchio*. He reflects on its dark themes, starkly contrasting it with the Disney adaptation. Cave discusses how the story helped him process personal grief and explores the transformative power of transgression and love. He also shares insights on creativity's messy nature, the emotional depth of male distress, and the richness of Collodi's writing, revealing the enduring relevance of this classic tale.

32 snips
Oct 23, 2025 • 55min
Why We Still Need Plato
Dr. Cornel West, a renowned philosopher and activist, dives into the enduring relevance of Plato's Republic. He passionately explores justice and the dangers of tyranny, linking philosophical inquiry to personal meaning. West critiques the state of American universities, urging a return to Socratic inquiry and the pursuit of truth. The conversation celebrates the integration of ancient wisdom with modern struggles, advocating for a philosophic life that transcends material concerns. Together, they reflect on how these timeless ideas can guide us in today's world.

43 snips
Oct 16, 2025 • 1h 8min
What Steven Pinker Taught this Pro Bodybuilder about Genetics
Mike Israetel, an exercise scientist and competitive bodybuilder, shares how Steven Pinker's *The Blank Slate* transformed his views on genetics and coaching. He argues that embracing our biological limits can lead to better training outcomes and humility in athletes' expectations. Israetel emphasizes the importance of a science-based approach to diet, criticizing fad fitness trends and advocating for foundational principles. He discusses how genetics shapes human potential and the need for realistic goals, while also providing practical advice for sustainable training.

18 snips
Oct 9, 2025 • 1h 8min
MeatEater’s Steven Rinella on Lessons from the Wilderness
Steven Rinella, an outdoorsman and founder of MeatEater, explores the profound influence of Jim Harrison's novel *Wolf*. He delves into the protagonist's struggle with bitterness and aimlessness, relating it to young men's search for meaning. Rinella discusses how Harrison’s chaotic writing style resonates today, while reflecting on the novel's themes of nature and personal restoration. His insights on raising children to connect with nature and the value of both consumptive and non-consumptive uses of the wild highlight a nuanced view of stewardship.

33 snips
Oct 9, 2025 • 59min
The Old Man and the Sea with Admiral James Stavridis
Admiral James Stavridis, a retired four-star U.S. Navy Admiral and bestselling author, dives deep into the impact of Ernest Hemingway’s The Old Man and the Sea on his life. He passionately discusses themes of resilience, ambition, and the mentor-mentee bond illustrated between Santiago and Manolin. Stavridis shares how reading has shaped his leadership style and emphasizes the importance of literature in understanding human experience. He also addresses common civilian misconceptions about the military and reflects on the future challenges he foresees.

Sep 22, 2025 • 57sec
Introducing: 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. Coming October 9th.
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