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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

52:33

The Ancient Jewish Wisdom Behind a $5 Billion Company

Old School with Shilo Brooks ·

2026/04/16

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount. As he built Kind Snacks into a $5 billion company, ‘Shark Tank’s Daniel Lubetzky didn’t turn to startup gurus or business manuals—but to a 2,000-year-old Jewish text. After the death of his father, a Holocaust survivor with whom he was deeply close, Daniel’s rabbi encouraged him to read Pirkei Avot, a collection of ancient wisdom on ethics, humility, and

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49:18

Neal Stephenson on AI, Rome, and How Civilizations...

Old School with Shilo Brooks ·

2026/04/09

Neal Stephenson, the prophetic author of cyberpunk classics like Snow Crash and The Diamond Age, has shaped how we imagine the future, from the metaverse to crypto to AI. His science fiction has a way of becoming reality.But Stephenson’s thinking is just as rooted in the past, returning to timeless questions of empire and decline. In this episode, he joins Shilo to discuss Edward Gibbon’s The History of the Decline and Fall of the Roman Empire, a sweeping work that has captivated readers from

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53:00

The Two Types of People Who Never Find Happiness

Old School with Shilo Brooks ·

2026/03/26

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount. Life is short. How do we live it well? Harvard professor Arthur Brooks has spent years studying happiness. In this episode, he joins Shilo to explore what neuroscience, faith, and philosophy reveal about how to live a happy life. Most of us are caught up in either the pursuit of empty pleasures or the pursuit of great achievement—“slacker” and “striver” extremes

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54:43

Hunting Humans for Sport

Old School with Shilo Brooks ·

2026/03/19

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount. Richard Connell’s 1924 short story “The Most Dangerous Game” tells of a hyper-sophisticated aristocrat who hunts human beings for sport on his private island. In this episode, best-selling author, screenwriter, and former Navy SEAL sniper Jack Carr joins Shilo to discuss the story’s enormous influence on the thriller genre, including on Carr’s own novels. The

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55:23

Joan Didion Knew What Hollywood Would Become

Old School with Shilo Brooks ·

2026/03/12

The perfect book to read around the Oscars this weekend? Joan Didion’s Play It as It Lays.In this episode, Shilo sits down with Peter Savodnik to discuss Didion’s 1970 novel—a book that seemed to anticipate everything ugly about Hollywood, celebrity culture, and the spiritual emptiness that we now take for granted on the red carpet and on social media. They break down why Didion’s story of an actress drifting through 1960s Los Angeles feels like it could have been written in 2026, how she saw the

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55:45

The NYC Public Defender Who Sends Books to Prisoners

Old School with Shilo Brooks ·

2026/03/05

In this episode, Shilo Brooks sits down with New York City public defender Ben Schatz to discuss the novel True Grit–and the nature of justice in America. Ben founded the nonprofit Books Beyond Bars, which sends requested books (not just random donations) to individuals locked in in New York jails and prisons, giving them dignity, mental escape, and intellectual stimulation. After discussing True Grit, Ben offers his critique of the U.S. criminal justice system itself: its coercive plea

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54:56

‘The Brothers Karamazov’ Helped Inspire the Catholic...

Old School with Shilo Brooks ·

2026/02/26

Alex Jones was using apps like Headspace and Calm to quiet his mind, but he had fallen away from his Catholic faith. Then he read The Brothers Karamazov, and everything changed.Alex, who went on to recommit himself to Christ and start Hallow, the Catholic prayer app with millions of users worldwide, believes Dostoevsky’s classic is the perfect book to read for Lent. In this conversation, Alex explains to Shilo how the novel mirrors Christian scripture, explores Dostoevsky’s answer to the problem

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49:04

‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a...

Old School with Shilo Brooks ·

2026/02/19

One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He owned a first edition. It pops up in emails and in photos, released by the House Oversight Committee, that show young women with quotes from the book written on their bodies.Lolita is about a 38-year-old man who kidnaps and serially rapes a 12-year-old girl. The book is not only a literary masterpiece, but a fixture of American pop

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54:12

The Secret Lives of Ordinary People

Old School with Shilo Brooks ·

2026/02/12

Dylan Thomas is one of the 20th century’s legendary poets. In this episode, English journalist David Aaronovitch joins Shilo to discuss Thomas’ 1954 play Under Milk Wood, a portrait of a small Welsh seaside town, originally produced for radio. With rich, musical language, Thomas reveals the secret interior lives of the villagers—their dreams, lusts, resentments, and longings—without condescension, inviting the listener to see that “these people are you” and to recognize one’s own hidden thoughts

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63:10

David Mamet vs. the Snobs

Old School with Shilo Brooks ·

2026/02/05

Pulitzer Prize–winning playwright David Mamet spent his childhood cutting class and reading at the local library. His first pick was Sinclair Lewis’s Main Street, which he pulled off the shelves at just 11 years old. Decades later, David thinks the book is terrible, its author “a horrible writer,” and its heroine an insufferable busybody. In this episode, Shilo pushes back, defending the novel and its protagonist. From there the conversation explodes into a larger discussion about taste, canon,

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52:57

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

Old School with Shilo Brooks ·

2026/01/29

In this episode, legendary comic Colin Quinn dives into a cult classic that still makes him cry with laughter: John Kennedy Toole’s A Confederacy of Dunces.The novel follows the misadventures of an overweight, pretentious misanthrope still living with his mother in 1960s New Orleans. It’s a book that turns fart jokes into high art. It’s also, somehow, a love story between a fat incel and a woke activist—a seemingly absurd pairing that just may be a prescient solution to our modern polarization

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48:44

Dante: The Most Famous, Least Read Poet

Old School with Shilo Brooks ·

2026/01/22

Dante Alighieri is one of the most consequential poets in human history, and his The Divine Comedy is essential to understanding Western civilization itself. And yet, though most of us have heard of Inferno, Dante remains one of the least read of all the greats. His masterpiece unfolds in three parts—Inferno, Purgatorio, and Paradiso—charting a journey from despair to redemption. For literature professor Joseph Luzzi, this journey was not abstract. After his wife was tragically killed in a car

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55:45

America’s Most Righteous War Produced Its Best...

Old School with Shilo Brooks ·

2026/01/15

In Venezuela, a U.S. operation that captured President Nicolás Maduro has sent shock waves through the hemisphere. In Iran, a deadly crackdown on nationwide protests has Washington threatening the possibility of direct military action. Meanwhile, war rages on from Ukraine to Sudan. All this instability and conflict makes now a good time to revisit the most acclaimed anti-war novel in American history: Catch-22.In this episode, Elliot Ackerman—a Marine Corps veteran and former CIA special

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52:53

Why ‘Middlemarch’ Changed This Catholic Priest’s Life

Old School with Shilo Brooks ·

2026/01/08

Middlemarch is George Eliot’s (real name Mary Ann Evans) masterpiece. The 900-page Victorian novel is about the people living in a fictional English town in a time of enormous changes.In this episode, Shilo Brooks sits down with Dominican friar Father Jonah Teller to discuss what makes the book worth reading. Their conversation tackles the novel’s major themes: marriage in all its mismatched forms, political upheaval around reform and the rise of liberalism, the promises and limits of scientific

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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

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