In this episode, American writer David Foster Wallace discusses his experiences following John McCain's campaign for the Republican presidential nomination in 2000. The podcast explores McCain's distinctive political style and its implications for American democracy. It also highlights the role of technology in Donald Trump's successful 2016 campaign and delves into Wallace's contrasting views on McCain and Trump's authenticity. The episode concludes by discussing the parallels between Trump's rise to power and the narrative described by Wallace, including themes of populism, technological shifts, and media coverage.

American essayist and novelist, Joan Didion, discusses her haunting and impressionistic writing style in her essay 'The White Album'. She explores the fracturing of America in the late 1960s, touching on topics such as Jim Morrison, the Manson murders, and the search for meaning in senseless acts of violence. Didion's ability to capture the divide between conventional and counterculture is highlighted, as well as her own struggle for coherence while maintaining a domestic life. The desire for ignorance in the face of significant events is contrasted with the ongoing crises of the world. Didion's journey with multiple sclerosis and her use of writing as an outlet to make sense of her experiences are also discussed.

Guest Susan Sontag, writer and critic, discusses her opposition to interpretation in art and criticism. The podcast explores how her argument can be applied to contemporary politics and the appeal of Donald Trump. It also touches on Sontag's influences, her transition from essayist to fiction writer, and the significance of knowing when to cease discussions.

James Baldwin, an influential American writer, discusses his essay 'Notes of a Native Son' which combines autobiography with a critique of America's racial politics. The podcast explores Baldwin's relationship with his father, the clash between North and South during war, the racial dynamics of World War II, and Baldwin's reflections on anger and white power.

Explore the radical ideas of Simone Weil, a French philosopher who rejected democracy, rights, personal identity, and scientific progress. Learn about her critiques of institutions, the concept of rights, and the distinction between living in a world of rights versus justice. Discover her insights on the horror of factory work, the recognition of suffering, and the paradoxes of modernity and cruelty.

George Orwell, author and political commentator, discusses the English resistance to fascism and the distinctive characteristics of English nationalism. He analyzes the presence and perception of the army in England, makes predictions and assumptions about the post-war era, and reflects on English politics, double standards, and hypocrisy.

Virginia Woolf, known for her essay 'A Room of One's Own,' discusses anger, power, sex, modernity, independence, and transcendence. The podcast explores the humor and gender bias in her essay, reflects on women's experiences in Oxbridge, and explores the unequal distribution of wealth and opportunities. It also examines Shakespeare's privilege and the challenges faced by women writers in breaking free from societal limitations, emphasizing the importance of having a personal space for expression.

This podcast explores Thoreau's 'Civil Disobedience' and his resistance against slavery and unjust wars. It discusses his views on democracy, majority opinion, and the importance of individual conscience. The speakers also delve into Thoreau's beliefs on climate change, institutional failure, and the world consumed by news and noise. They examine his actions in protesting slavery and awakening his fellow citizens, highlighting his impact on civil disobedience movements.

Explore David Hume's essay on public debt and credit and its relevance to American politics. Delve into Hume's controversial ideas on suicide, mockery, and the morality of ending one's life. Discover Hume's perspectives on the dangers and unsustainability of borrowing, the impact of a national debt-driven economy, and the relationship between debt, democracy, and political responsibility. Uncover the complexities surrounding suicide, obligations, and the role of public debt in sustaining lives.

Learn about Montaigne, the man who invented a new way of writing and being read. From the fear of death to the joys of life, Montaigne wrote the book of himself, exploring topics such as atheism, faith, sex, religion, and more. Discover the open-ended and adventurous nature of essays, as well as Montaigne's unique exploration of animals, randomness, simplicity, and complexity in philosophy.