Debates about AI typically deal with its immediate material consequences, from cybersecurity and infrastructure to plagiarism and copyright. Yet most people deal with AI as a generative consumer product that raises longer-term questions about its cultural effects on American society, human art, and ultimately, our souls. What is the role of the artist, for example, when a bot can crank out the same thing more quickly and efficiently?

To help answer that question, as we continue Season 6, I have as our guest the playwright, novelist, and essayist Matthew Gasda. The author of the novels The Sleepers (2025) and Stranger Beauty (2026), he has written, produced, and directed over thirty plays, including Dimes Square, Zoomers, and Doomers, with his former production company, The Center for Theatre Research.

Today, drawing on his upcoming book, Futurepast (Encounter Books 2026), alongside Stranger Beauty, his many essays on culture and technology, as well as his Ted Talk about training an LLM on his own works, we discuss the future of the creative arts in the AI age.

We also touch upon the paradoxes of Jorge-Luis Borges, Harold Bloom’s literary criticism, what is different about large language models, why Kafka felt older than his predecessors, the mysteries of poetic inspiration and of the soul, what hosting live theater was like during the pandemic, the possibility of secular monasteries, how to use AI as a competitor to root out artistic complacency, and the unpredictable prospects for cultural renewal.

Hosted by Ryan Shinkel, Madison’s Notes is the podcast of Princeton University’s James Madison Program in American Ideals and Institutions. The transcript for this interview is available on the JMP substack page, “Madison’s Footnotes.

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While many know that Mark Twain created some of the most famous characters in literature—Tom Sawyer and Huckleberry Finn, Jim and Puddn’head Wilson—too few have understood that the Missouri author wasn’t only America’s greatest humorist, but also one of its most subtle political thinkers. But what was the political philosophy of the elusive and ironic Mark Twain for his new democratic America?

To help answer that question, as we continue Season 6, I have as our guest Ivan Kenneally. A contributor to The New Atlantis and First Things, among other publications, he wrote an essay for The Hedgehog Review on modern reactions to Twain’s Adventures of Huckleberry Finn (1884), titled: “Mark Twain’s Absurd, Noble America,” which we will be discussing today.

We also talk about the travels of the two runaways Huck and Jim, along with their many disguises and rouses, how Americans like Tom Sawyer read European literature too dogmatically, the conmen Twain depicts in the Duke and Dauphin, technical versus tacit knowledge in his memoir Life on the Mississippi, contemporary interest in Twain from Ron Chernow and Percival Everett, the nature of irony as well as the poverty of modern comedy, and what philosophers and comedians alike can learn from the Missouri author and philosopher.

Hosted by Ryan Shinkel, Madison’s Notes is the podcast of Princeton University’s James Madison Program in American Ideals and Institutions. The transcript for this interview is available on the JMP substack page, “Madison’s Footnotes.

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Whether recovering a lost history or charting a new land, scholars and explorers alike often hit at frontiers not only of place, but also knowledge. When the evidence only goes so far, what is the right way to advance?

The answer is to make a conjecture: an educated guess that discourses on what is likely the case. Historical examples range from Italian humanists stealing manuscripts from monasteries and reconstructing classical languages, to Jesuit missionaries speculating about land bridges to the Americas, and even Renaissance magicians pioneering in alchemy and astrology.

This collective practice is called “conjectural history,” and its roots go far back. But how far back? To answer that question, as we continue Season 6, I have as our guest, Professor Anthony Grafton.

A former president of the American Historical Association, and the Emeritus Henry Putnam University Professor of History at Princeton University, Grafton is a scholar of early modern Europe and written history, a frequent contributor to the New York Review of Books and London Review of Books, and the author of many books such as The Footnote (1997) and Magus (2023). Today, we will discuss his current project on “conjectural history.”

We discuss the use of conjectural versus counterfactual history, its founders in Herodotus and Thucydides, and proponents like the explorer Jose de Acosta, S.J. and the scholar Lorenzo Valla. Also discussed are Hobbes, Locke, and Rousseau, the birth of modern science from renaissance magic, C.S. Lewis’ The Discarded Image, recent scholarship on premodern eyewitness testimony to the supernatural, the magician Henry Cornelius Agrippa, and the best lost spots of Princeton University.

Hosted by Ryan Shinkel, Madison’s Notes is the podcast of Princeton University’s James Madison Program in American Ideals and Institutions. The transcript for this interview is available on the JMP substack page, “Madison’s Footnotes.

Chapter Headings:

• 00:00 | Introduction & What is Conjectural History
• 4:30 | The Scottish Enlightenment vs. the Renaissance Tradition
• 11:42 | Conjectural History & a Case Study: Jose de Acosta
• 19:30 | Theology, Science & The Renaissance
• 26:19 | Lorenzo Valla and the Donation of Constantine
• 38:19 | Conjecture, Divination, and Magic
• Closing | Reflections: History, Belief, and Closing Thoughts

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