Old School with Shilo Brooks

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.

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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.

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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.
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