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Old School with Shilo Brooks

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Rating
★★★★★
4.8
from
193 reviews
This podcast has
35 episodes
Language
English
Explicit
No
Date created
2025/09/23
Latest episode
2026/06/25
Average duration
50 min.
Release period
9 days

Description

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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Check latest episodes from Old School with Shilo Brooks podcast


A Note From Shilo
2026/06/25
A message from our host. Learn more about your ad choices. Visit megaphone.fm/adchoices
What ‘The Future Is Female’ Has Meant for Men
2026/06/18
For decades, the fight for gender equality has squarely focused on lifting women up—in the workplace, politics, and beyond. But according to Richard Reeves, president of the American Institute for Boys and Men, it’s the men who now need support.  From childhood, boys are falling behind in school. Men are trailing women in college completion by an even wider margin than existed (in the opposite direction) when Title IX became law in 1972. They also die by suicide about four times more often, with especially troubling increases among younger men over the past two decades. In this episode, Reeves sits down with Shilo Brooks to discuss why the struggles facing boys and men have become politically impossible to discuss, why they need to stop hearing that “the future is female” and that their masculinity is “toxic,” and what the specific policies are that he believes will help them.  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
Walter Isaacson on the Sentence That Created America
2026/06/11
If America has a mission statement, it is this:   “We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness.”  In a special conversation recorded at the George W. Bush Presidential Center, acclaimed biographer Walter Isaacson discusses his new book, The Greatest Sentence Ever Written, and the extraordinary story behind the Declaration of Independence’s most famous line. What happened behind the scenes as Thomas Jefferson, John Adams, Benjamin Franklin, and the other founders argued over, revised, and refined the words that would become America’s founding creed? Plus: the tension between individual liberty and the common good, the complicated relationship between Jefferson and Adams, and the enduring challenge of living up to ideals that were revolutionary in 1776 and remain aspirational 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. 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
The WWII Novel That Explains America
2026/06/04
In this special episode, Shilo Brooks is joined by Pulitzer Prize–winning historian Jon Meacham at the Jack Miller Center’s annual summit on civic education.  They took the stage at the National Constitution Center in Philadelphia, the perfect setting for a discussion about one of Meacham’s favorite books: The Winds of War. Written by Herman Wouk and published in 1971, The Winds of War is an epic historical novel that follows an American family through the tumult of World War II.  In their smart, often funny, and deeply moving conversation, Meacham also reflects on why World War II was such a pivotal moment in shaping the unique American identity; the other essential books, events, and moments every citizen should know about to better understand America; and the differences between patriotism and nationalism.  At a moment when our politics feel so fractured, studying history reminds us of an enduring truth: Ordinary people can rise to extraordinary challenges. 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
Agatha Christie and the Kidnapping That Inspired Her Greatest Mystery
2026/05/28
In this episode, Shilo sits down with veteran journalist Joe Nocera for a deep dive into the world’s best-selling novelist, Agatha Christie.  Nocera’s new investigative podcast is all about the Charles Lindbergh, Jr., kidnapping, one of history’s most infamous crimes, and a key inspiration behind Christie’s Murder on the Orient Express.  They dig into why mystery fiction matters so deeply, the puzzle-like satisfaction of solving the crime, the bloodless elegance of Christie’s plots, and the rare comfort of a story that always resolves with true justice. They break down how Christie drew directly from the Lindbergh kidnapping to craft her most famous work and examine what the Lindbergh case reveals about a society so hungry for retribution that it may have sent the wrong man to the electric chair. 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
Inside the Supreme Court with Amy Coney Barrett
2026/05/21
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 not the hyper-partisan institution that people think it is, and much more.  It’s a thoughtful conversation that offers a more nuanced look at the highest court in the land.  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
A New Series From The Free Press | The Lindbergh Conspiracies
2026/05/19
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. --- EP01 | The Broken Window One night in March 1932, the infant son of aviator Charles Lindbergh is taken from his nursery. A warped window, a ladder, and a ransom note mark the beginning of a case that will grip the world and launch a hundred conspiracy theories. Ninety-four years later, we return to the scene of the crime to ask: What really happened that night? Learn more about your ad choices. Visit megaphone.fm/adchoices
Roald Dahl: Genius and Bigot
2026/05/07
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 approach brilliant art produced by morally compromised artists? Throughout history, some of the world’s preeminent literary geniuses have also been deeply bigoted, even monstrous people. In this episode, Shilo is joined by Eli Lake, host of Breaking History, for a conversation about these geniuses, from Voltaire to Norman Mailer, and why we should read their work despite their odious prejudices. 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
How Sports Became Our Civic Religion
2026/04/30
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 about winning—and losing?  They dig into why sports matter so deeply: tribal belonging, meritocracy, tradition, and the rare intensity of collective experience that borders on the religious. Thompson also explains why the most passionate fandoms often emerge in poor, deindustrialized towns. They also examine the controversies and contradictions of modern sports, from coaches and universities running de facto professional programs to the rise of gambling and debates over salary caps. 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
The Ancient Jewish Wisdom Behind a $5 Billion Company
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 leadership. In this episode, Daniel explains to Shilo how its teachings shaped both his leadership and Kind’s culture by reminding him to question his ego, resist yes-men, stay grounded, and learn from everyone. More than moral philosophy, Pirkei Avot became a practical guide—anchoring his values while building an iconic brand. 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
Neal Stephenson on AI, Rome, and How Civilizations Decline
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 Winston Churchill to Iggy Pop. Was Rome undone by barbarians, Christianity, decadence, or elite failure? And what do those patterns reveal about our own age of technological upheaval—and the risks of AI? 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
The Two Types of People Who Never Find Happiness
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 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. 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
Hunting Humans for Sport
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 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. 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
Joan Didion Knew What Hollywood Would Become
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 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. 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
The NYC Public Defender Who Sends Books to Prisoners
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 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. Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe. The Free Press earns a commission from any purchases made through all book links in this article. Learn more about your ad choices. Visit megaphone.fm/adchoices

Podcast reviews

Read Old School with Shilo Brooks podcast reviews


4.8 out of 5
193 reviews
★★★★☆
JuliannetteB 2026/06/26
Mother of Future Men
I love listening to this show to gain perspective and raise my boys to be great men. I did have a problem with your comment about men being interested...
★★★★★
Ben Connelly 2026/04/10
Great to see Shilo got his own podcast!
As a former student of Shilo’s from over a decade ago, I was very excited to hear about this podcast and have been listening from near the start. I lo...
★★★★★
CMac2834 2026/03/29
Full of Depth
This is the kind of podcast all can get value from. Full of insight and depth on a variety of issues.
★★★★★
Machiavelli51 2026/02/27
Outstanding
My favorite podcast! Love the equanimity, the gentle pressing of guests on their more outlandish opinions, the mutual exploration of topics that matte...
★★★★★
Eamon Parker 2026/02/26
You hit the nail on the head
Regarding the episode about Lolita—you are invoking the concept of Disordered Love when you refer to novel of awful human behavior.
★☆☆☆☆
EM_918 2026/01/08
Guests?
I was looking forward to this pod, but In the Middlemarch episode, instead of a discussion, the guest can only manage to interject single syllable re...
★★★★★
Rachel CP4 2025/12/29
More please
Im not the target audience but I love this show. Shiloh Brooks leads a great interview and the guests surprise me. Keep making more episodes.
★★★★★
Mrs. Jewely 2025/12/22
Fantastic
I binged all of the available episodes and I’m listening to them again.
★★★★★
miss lina b. 2025/12/20
More, please!
This pod will make you smarter, nicer and prettier. Nick Cave and Richard Dawkins talk books…what else do you need to know?
★★★★★
Amichai Magen 2025/12/16
Love it!
Love the philosophy behind this podcast just as much as the quality of the discussants (not the usual suspects) and Shilo Brooks’s fresh style. Keep i...
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