Old School with Shilo Brooks

The Free Press
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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. New episodes out every Thursday.  Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks

  1. -2 J

    The Secret Lives of Ordinary People

    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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    54 min

  2. 5 FÉVR.

    David Mamet vs. the Snobs

    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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    1 h 3 min

  3. 29 JANV.

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

    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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    53 min

  4. 22 JANV.

    Dante: The Most Famous, Least Read Poet

    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. Learn more about your ad choices. Visit megaphone.fm/adchoices

    49 min

  5. 15 JANV.

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

    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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    56 min

  6. 8 JANV.

    Why ‘Middlemarch’ Changed This Catholic Priest’s Life

    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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    53 min

  7. 18/12/2025

    The Lost Art of Taking the Piss with Richard Dawkins

    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.Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    41 min

  8. 11/12/2025

    Living Through the Fall of a Regime

    “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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. Learn more about your ad choices. Visit megaphone.fm/adchoices

    1 h 5 min
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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. New episodes out every Thursday.  Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks

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