Old School with Shilo Brooks

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.

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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.
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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.
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