Old School with Shilo Brooks

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.

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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.

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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