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
Episodes
May 21, 2026 • 51 mins
In this special episode, taped live at the George W. Bush Presidential Center, Shilo sits down with Supreme Court Justice Amy Coney Barrett for a wide-ranging interview on the law.
They discuss Barrett’s lifelong love of reading, her tumultuous confirmation process, the Constitution and what it should take to amend it, how she approaches cases where her interpretation of the law differs from her personal beliefs, why the Court is...
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May 19, 2026 • 43 mins
Hi Old School listeners! Veteran reporter Joe Nocera has launched a six part series about the Lindbergh kidnapping. Enjoy episode one here and then head on over to The Lindbergh Conspiracies feed for the rest of the season. Joe will be joining me next week to discuss Agatha Christie and how she was inspired by this very case.
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EP01 | The Broken Window
One night in March 1932, the infant son of aviator Charles Lindbergh is ...
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May 7, 2026 • 49 mins
For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.
Roald Dahl gave the world Matilda, James and the Giant Peach, and Charlie and the Chocolate Factory. He was also a vicious antisemite.
A Broadway play about Dahl’s legacy; the new Michael Jackson biopic; Kanye West’s attempted redemption arc; all of these have the culture asking again: How do we ap...
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April 30, 2026 • 51 mins
For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.
In this episode, Shilo sits down with sportswriter Wright Thompson to explore what the ESPN mainstay has learned from decades of covering elite athletes such as Tiger Woods and Michael Jordan. Does greatness require rage, dysfunction, or “daddy issues”? And what does GOAT culture teach young men abo...
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April 16, 2026 • 52 mins
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...
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April 9, 2026 • 49 mins
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 th...
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March 26, 2026 • 53 mins
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...
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March 19, 2026 • 54 mins
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 influe...
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March 12, 2026 • 55 mins
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 A...
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March 5, 2026 • 55 mins
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...
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February 26, 2026 • 54 mins
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 mir...
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February 19, 2026 • 49 mins
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 bo...
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February 12, 2026 • 54 mins
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 t...
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February 5, 2026 • 63 mins
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 th...
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January 29, 2026 • 52 mins
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...
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January 22, 2026 • 48 mins
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 journe...
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January 15, 2026 • 55 mins
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, El...
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January 8, 2026 • 52 mins
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 ref...
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December 18, 2025 • 41 mins
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 shar...
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December 11, 2025 • 64 mins
“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 ...
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