

Old School with Shilo Brooks
The Free Press
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
Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks
Episodes
Mentioned books

33 snips
Mar 26, 2026 • 53min
The Two Types of People Who Never Find Happiness
Arthur Brooks, Harvard professor and author who studies the science of happiness. He contrasts the lives of frantic strivers and complacent slackers. He discusses Seneca, the role of faith and learning, why love and relationships matter, and how accepting suffering deepens meaning.

18 snips
Mar 19, 2026 • 55min
Hunting Humans for Sport
Jack Carr, best-selling author and former Navy SEAL sniper, reflects on how Richard Connell’s “The Most Dangerous Game” shaped modern thrillers. He discusses the moral line between killing and murder. Carr weighs recent U.S. strategies, warns about regime change in Iran, and explains his push to rename the Department of Defense. Short, sharp conversations on violence, literature, and service.

7 snips
Mar 12, 2026 • 55min
Joan Didion Knew What Hollywood Would Become
Peter Savodnik, editor and cultural critic, discusses Joan Didion and her novel Play It as It Lays. He traces Didion’s prophetic view of Hollywood, the emptiness of modern celebrity, and how her precise detail and skepticism toward 60s feminism still cut through contemporary culture. Short, sharp takes connect the book’s mood to today’s red carpets and social media spectacle.

17 snips
Mar 5, 2026 • 56min
The NYC Public Defender Who Sends Books to Prisoners
Ben Schatz, a New York City public defender who founded Books Beyond Bars to send requested books to incarcerated people, discusses True Grit and the role of literature behind bars. He describes how books offer escape and dignity, critiques plea bargaining and mass incarceration, and reflects on compassion, mental health in prisons, and practical ideas to improve the system.

15 snips
Feb 26, 2026 • 55min
‘The Brothers Karamazov’ Helped Inspire the Catholic App Hallow
Alex Jones, founder and CEO of Hallow who returned to Catholicism and built a prayer app, describes how The Brothers Karamazov reshaped his faith. He discusses the novel’s mirror of scripture, Dostoevsky’s take on suffering and love, the moral arcs of the Karamazov brothers, and why he used a Silicon Valley startup model to spread daily prayer.

14 snips
Feb 19, 2026 • 49min
‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic
Shilo Brooks, a literary commentator, unpacks Vladimir Nabokov's Lolita and its fraught cultural life. He traces Humbert Humbert's unreliable narration and why readers can be unsettlingly sympathetic. He examines how the book was misread, its pop‑culture glamorization, and what careful reading of the novel teaches us about moral complicity and literary craft.

Feb 12, 2026 • 54min
The Secret Lives of Ordinary People
David Aaronovitch, award-winning journalist and author, reflects on Dylan Thomas’s Under Milk Wood and its impact on his life. He recalls hearing the radio original, explains why the medium matters, and celebrates Thomas’s musical language. They explore the play’s tender view of ordinary people, the narrator’s godlike voice, and how the work deepened his compassion.

13 snips
Feb 5, 2026 • 1h 3min
David Mamet vs. the Snobs
David Mamet, Pulitzer Prize–winning playwright and screenwriter, reflects on a childhood of library browsing and how it forged his tastes. He sparks a lively clash over Sinclair Lewis’s Main Street. The conversation widens into debates about taste, cultural authority, the decline of browsing, and why he rejects school-imposed reading.

19 snips
Jan 29, 2026 • 53min
Colin Quinn on Incels, Woke Activists, and Peaking at 14
Colin Quinn, veteran New York comic and author known for sharp stand-up and one-man shows, chats about A Confederacy of Dunces and why it still makes him howl. He links Ignatius to modern online outrage and incel culture. He unpacks the novel’s odd love story between opposites, the craft that lifts low comedy into literature, and how reading fuels stand-up material.

7 snips
Jan 22, 2026 • 49min
Dante: The Most Famous, Least Read Poet
Literature professor Joseph Luzzi, an expert in Italian literature and author, shares how Dante's The Divine Comedy helped him cope with the tragic loss of his pregnant wife. He discusses Dante's journey from despair to redemption, breaking down its three parts: Inferno, Purgatorio, and Paradiso. Luzzi highlights the poem as a map for navigating grief and how literature offers solace in tough times. He also stresses Dante's role in shaping modern literature and the importance of making humanities accessible to everyone.


