Brian Jordan Alvarez, an actor and creator of the FX show 'English Teacher,' dives into the chaotic world of public schools, where book bans and tech restrictions fuel comedic inspiration. He shares insights on his viral TikTok fame and the challenges of portraying a gay Latino teacher in a conservative Texas setting. The conversation explores the ties between humor and identity, the transformative power of literature in education, and the importance of clarity in performance, especially in comedy.

Newt Gingrich, former Speaker of the House and political commentator known for his influential role in the Republican Revolution, shares his insights on Trump's potential second term. He reflects on Trump's combative political style, moral compromises within the GOP, and the challenges facing Ukraine. Gingrich discusses evolving U.S. immigration policies and the implications of Trump's governance, particularly around abortion. He also addresses the fallout from January 6th and how figures like J.D. Vance might shape the future of Trumpism and political dynamics.

Kamala Harris, a prominent political figure and presidential candidate, delves into the challenges she faces regarding her stance on the Gaza conflict. Many Arab American and Muslim voters express discontent with the Biden Administration's policies, threatening her electoral prospects. Abbas Alawieh, a founder of the Uncommitted Movement, shares insights on the moral dilemmas faced by Muslim Democrats. With tensions rising, voters are caught between strategic voting and their principles, as candidates like Jill Stein gain traction in Michigan.

Sebastian Stan stars as a young Donald Trump in the film 'The Apprentice,' shedding light on his formative relationship with notorious lawyer Roy Cohn, played by Jeremy Strong. Gabriel Sherman, the film's writer, reveals how Cohn mentored Trump in the dark arts of power brokering, which shaped Trump's rise in New York society. Sherman emphasizes the film's humanist angle, defying simple political categorization. The production faced challenges, including threats from Trump himself, highlighting Hollywood's hesitance in tackling such a controversial figure.

Timothy Snyder, a prominent historian and author specializing in Eastern European history, shares insights from his experiences in Ukraine during the ongoing war. He discusses the deep conviction among Ukrainians that they can prevail, rooted in their resilience and history. Snyder emphasizes that true freedom is an active struggle rather than merely the absence of tyranny. He reflects on the lessons from Ukraine that resonate globally, urging a comprehensive approach to liberation that empowers individuals, rather than waiting for others to deliver freedom.

Sarah Longwell, a political strategist and founder of Longwell Partners, dives into the shifting sentiments of Republican voters toward Trump. With her extensive experience in analyzing swing-state voters, she discusses the potential fallout from January 6 and how many are reconsidering their support. Longwell highlights the risks for Trump and the growing appeal of centrist candidates like Kamala Harris, emphasizing the emotional and ideological factors shaping voter decisions. The conversation provides a fascinating glimpse into the evolving Republican landscape ahead of the 2024 election.

Bridget Kearney, the bassist for Lake Street Dive, draws inspiration from the legendary Billy Joel as they share their journey from performing in small venues to the grandeur of Madison Square Garden. They reflect on their unique songwriting processes, the importance of camaraderie, and their political anthem 'Shame, Shame, Shame.' The band aims to evoke an intimate vibe at big shows, hoping to create connections like a 'gig at a dive bar.' They also discuss their new songs and the blend of themes in their music, full of emotion and hope.

Josh Shapiro, the newly elected Pennsylvania governor, discusses the shifting political landscape of his state, a crucial battleground for the upcoming presidential election. He emphasizes the need for Democrats to appeal to Independents and moderate Republicans, noting that genuine engagement with diverse communities is essential. Shapiro also reflects on the implications of political rhetoric and how inclusivity can shape campaigns. Finally, he shares insights on Kamala Harris's strategies to communicate her policies effectively in a state that is vital for any candidate's success.

Patti LuPone has been a mainstay on Broadway for half a century. She’s appeared in some 30 Broadway productions and has won three Tony Awards for her roles in “Evita,” “Gypsy,” and “Company.” And somehow, LuPone’s career seems to be picking up steam in its sixth decade. Now LuPone is returning to Broadway in “The Roommate,” a play she’s starring in alongside Mia Farrow.  At the same time, she is débuting in the Marvel Cinematic Universe, playing a witch in the miniseries “Agatha All Along.”  The staff writer Michael Schulman first wrote about LuPone (in one strange, forgotten dead end of her career) in 2019, and recently spoke with LuPone at her home.  Is it true, he wanted to know, that LuPone recently had Aubrey Plaza—her castmate on “Agatha”—for a short-term roommate?  Plaza had been offered her first role in a play, as LuPone relates it, and “she'd never been onstage. I know from years of experience how it can shock you, what is required of you to be a stage actor.” LuPone, the veteran, “was concerned for her. I said, Why don't you just stay with me and let me walk you through this as you come home like a deer caught in the headlights. … I did do her laundry, and I did make her soup.” 

In this engaging discussion, Marc Elias, a prominent attorney celebrated for his pivotal role in the 2020 election lawsuits, shares insights on the rising dangers for the upcoming 2024 elections. He warns of more competent strategies from Trump and allies, emphasizing that election-denying officials now hold significant power in swing states. Elias predicts Trump's inevitable claim of victory across all states and discusses the ongoing threats to democratic processes and voting rights, urging the need for vigilance amidst growing misinformation.