James Carville, a legendary political consultant and former CNN contributor, dives into a variety of topics. He reflects on his upbringing in a devout Catholic family and critiques the oversimplified views of marginalized groups. Discussing Kamala Harris, he highlights her effective rhetoric and the need for authentic messaging. Carville also shares insights on Bill Clinton’s charisma and the decline of the Catholic Church's influence. Lastly, he explores the complex legacy of Donald Trump, urging a more nuanced understanding of his impact.

Jeffrey Toobin, a lawyer and CNN's chief legal analyst, shares insights from his extensive career, shaped by parents who were both journalists. He discusses the evolution of executive power and the absence of congressional war declarations since WWII, spotlighting the tensions in U.S. foreign policy. Toobin also highlights the transitional nature of presidential accountability, informed by historical investigations from Nixon to Trump. Finally, he addresses the impact of fragmented media landscapes on political dialogue and public perceptions.

Anne Applebaum, a renowned journalist and historian at The Atlantic, discusses the rise of modern autocracies and the complexities they present to opposition movements. She delves into the financial tactics of kleptocracies and the chilling effects of surveillance technologies. The conversation touches on Trump's views on dictators, the normalization of autocratic values in U.S. politics, and the challenges posed by regimes like Putin's in Ukraine. Applebaum also reflects on why contemporary leaders often lack grand ideologies, favoring cynicism instead.

Author and journalist Lionel Shriver discusses human limitations, feminism, gender nonconformity, and political extremes. She reflects on her upbringing, name change, and societal beliefs, challenging notions of equality and individuality in a changing society.

Legendary British actor, Stephen Fry, discusses growing up in Norfolk, his mom's Jewish ancestry, embracing Englishness, and his struggles with bipolar depression. He delves into his influences, including Oscar Wilde, Gore Vidal, Auden, and more. The conversation also explores his personal journey, LGBTQ+ culture in literature, Brexit motivations, and reflections on government systems and life evolution.

Erick Erickson, a radio host and writer, discusses the decline of churchgoing, the rise of conspiracy theories, and the impact of Covid on religious practices. They delve into topics like Gnosticism, the Bible canon, and the Resurrection. The conversation also touches on transgenderism, climate change, and the challenges of faith in a scientific world.

Tim Shipman, Chief political commentator at The Sunday Times, talks about UK politics. Topics include Boris Johnson's controversies, Rishi Sunak's challenges, and Nigel Farage's impact. They discuss Brexit, Tory power, and election blunders.

Elizabeth Corey, an academic and writer, discusses the life and philosophy of Michael Oakeshott, emphasizing his views on individualism, liberal education, and opposition to identity politics. They explore Oakeshott's critical view of careerism, the virtue of changing one's mind, and the importance of living in the present moment. The conversation touches on thinkers like Augustine and Montaigne, highlighting Oakeshott's social adeptness and preference for meaningful conversations over winning debates.

Writer and reporter Nellie Bowles discusses growing up with divorced parents in SF, working in journalism, and her new book. They touch on the changing media landscape, ideological pressure in the industry, and challenges of maintaining independence. Reflecting on legacy institutions like the NYT and questioning narratives in journalism.

Guest George Will discusses topics such as presidential power, stopping Putin, socialism, just war theory, collectivism vs national security, Reagan's economic policies, and the paradoxes of American conservatism.