Old School with Shilo Brooks

The Free Press
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19 snips
Jan 29, 2026 • 53min

Colin Quinn on Incels, Woke Activists, and Peaking at 14

Colin Quinn, veteran New York comic and author known for sharp stand-up and one-man shows, chats about A Confederacy of Dunces and why it still makes him howl. He links Ignatius to modern online outrage and incel culture. He unpacks the novel’s odd love story between opposites, the craft that lifts low comedy into literature, and how reading fuels stand-up material.
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7 snips
Jan 22, 2026 • 49min

Dante: The Most Famous, Least Read Poet

Literature professor Joseph Luzzi, an expert in Italian literature and author, shares how Dante's The Divine Comedy helped him cope with the tragic loss of his pregnant wife. He discusses Dante's journey from despair to redemption, breaking down its three parts: Inferno, Purgatorio, and Paradiso. Luzzi highlights the poem as a map for navigating grief and how literature offers solace in tough times. He also stresses Dante's role in shaping modern literature and the importance of making humanities accessible to everyone.
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12 snips
Jan 15, 2026 • 56min

America’s Most Righteous War Produced Its Best Anti-War Novel

Elliot Ackerman, a Marine Corps veteran and bestselling author, dives into the timeless relevance of Joseph Heller's "Catch-22." He discusses how the novel's absurdism mirrors current global conflicts like those in Venezuela and Iran. Ackerman explores the contradictions of war, the role of humor in depicting its harsh truths, and critiques the bureaucracy that obscures human suffering. He also reflects on the hidden costs of war and the importance of varied war literature for those who serve, connecting past and present with poignant insights.
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13 snips
Jan 8, 2026 • 53min

Why ‘Middlemarch’ Changed This Catholic Priest’s Life

Father Jonah Teller, a Dominican friar at St. Joseph's Church, discusses how George Eliot's 'Middlemarch' transformed his perspective on life. He explores themes of marriage, political change, and the significance of mundane choices. Father Jonah emphasizes Eliot’s belief in the importance of seemingly insignificant lives and how character-driven storytelling illuminates human nature. They delve into the novel's insights on religion, morality, and the value of great literature in shaping virtues, all while addressing modern dilemmas through the lens of Victorian narratives.
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Dec 18, 2025 • 41min

The Lost Art of Taking the Piss with Richard Dawkins

Richard Dawkins, a prominent evolutionary biologist and author, shares his love for the humor of P.G. Wodehouse, revealing how his wit provides a delightful escape from serious discourse. They discuss Wodehouse’s sharp satire of the British aristocracy, his whimsical characters like Jeeves, and the unique brilliance of his language. Dawkins also reflects on comedy’s deep roots in tragedy and its role in modern society, critiquing the lack of humor in today’s intellectual landscape while celebrating Wodehouse’s enduring legacy.
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9 snips
Dec 11, 2025 • 1h 5min

Living Through the Fall of a Regime

Dominic Green is a historian, author, and columnist known for his insights on history and politics. In this discussion, he explores the themes of decline in today's American and British establishments, drawing parallels to Lampedusa's novel, The Leopard. Green delves into the consequences of a failing regime, discussing aristocratic decay and the elitism that breeds contempt for the populace. He also warns that ignoring societal decline could lead to a loss of legitimacy for today's leaders, urging a need for active adaptation to preserve core values and stability.
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20 snips
Dec 4, 2025 • 1h 3min

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

Ryan Holiday, author and founder of The Daily Stoic, discusses the philosophical depths of Walker Percy’s *The Moviegoer*. He argues it’s a more mature counterpart to *The Catcher in the Rye*, delving into the protagonist's existential malaise amidst postwar comfort. Holiday emphasizes the importance of savoring literature over speed reading and explores themes of modern life's meaning, social media performance, and the search for depth in everyday existence. He also highlights how Stoicism offers a remedy for our chaotic modern lives.
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53 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.
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19 snips
Nov 13, 2025 • 1h 1min

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.
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106 snips
Nov 5, 2025 • 1h

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.

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