Stay ConnectedFewer 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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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 that keep us in a doom loop, like addicts.
The real keys to happiness are deepening relationships, cultivating faith, and committing to lifelong learning, without concern for external validation or reward. Above all, we must learn to love and be loved and to accept suffering and heartbreak as features, not bugs, of a meaningful life.
Arthur’s latest book, The Meaning of Your Life: Finding Purpose in an Age of Emptiness, comes out March 31, 2025, pre-order your copy today at the link!
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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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 conversation explores the thin line between killing and murder—and when violence becomes necessary for peace.
Carr also explains why he is skeptical of current U.S. operations against Iran and talk of regime change, and recounts his successful push to change the name of the U.S. Department of Defense back to the Department of War in 2025.
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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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 darker underside of feminist “liberation” long before it was fashionable to question it, and why the real problem with today’s young stars is that we hear from them constantly, leaving little of the mystique that once defined celebrity.
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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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 bargaining, racism, overburdened defenders and judges, and prisons that function more as warehouses than places of rehabilitation, especially for mentally ill and addicted people.
Throughout, the conversation links the moral center of True Grit to real‑world questions about what justice is, who deserves mercy, and how to look past someone’s criminal history.
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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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 of evil, and shares why he chose the Silicon Valley start-up model as his unlikely but powerful way to bring millions of people back to daily prayer.
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.
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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 culture. The illicit relationship it depicts is often glamorized in film, music, and art.
Today, Rafaela Siewert interviews Shilo Brooks about Lolita–and about how a novel narrated by a homicidal pedophile rapist came to occupy such a prominent place in American life.
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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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 in even the most comic or disturbing characters.
They discuss how the play is exceptional in a flattened, cliché-ridden culture obsessed with exterior image and dismissive of the complexity of ordinary people.
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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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, authority, why David distrusts teachers, critics, and arts institutions that try to tell the public what’s good for them, and how he decides what’s worth reading—or throwing across the room.
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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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 problem.
Plus, Colin and Shilo dig into the parallels between great comic writing and great standup: Both give language to things audiences half-know but have never quite articulated, making the familiar suddenly, painfully funny.
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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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 accident while eight months pregnant, leaving him widowed and a father on the same day, the epic poem helped him overcome his grief and build a new life. In this episode, Shilo and Joseph sit down to discuss Dante’s genius.
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.
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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 operations officer—sits down with Shilo Brooks to unpack Joseph Heller’s classic satire, why it speaks so sharply to this moment, and how Americans have been shielded for the past few decades from the true costs of war.
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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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 progress, and the facets of human nature revealed in ordinary domestic life. They highlight Eliot’s conviction that there are no truly insignificant lives—that quiet, “unhistoric” acts and small, private decisions are of great importance.
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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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 Wodehouse’s outrageous similes and linguistic brilliance to his internment by the Nazis during World War II and to a larger question: why has humor been evacuated from modern intellectual life?
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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“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 order and the disorientation that accompanies the fall of a ruling class.
In this episode, historian Dominic Green joins Shilo Brooks to explore why today’s American and British establishments resemble that fading aristocracy: oligarchic, overregulated, technologically backward, and increasingly contemptuous of the people they rule.
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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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 responsibilities of marriage and everyday life. Brooks and Holiday explore the book’s philosophical themes and its continued relevance in a media-saturated world where many of us, still starved for meaning, try to turn our own existence into a social-media performance.
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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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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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.
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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.
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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.
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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.
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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 dreaming of becoming LeBron James and start maximizing the hand they’re dealt.
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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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 the wilderness. Rinella lays bare the novel’s darker undercurrents and why it has appeal for young men lacking purpose.
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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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 reading books has made him a more effective leader.
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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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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