Cultural critics Alexandra Schwartz, Naomi Fry, and Vinson Cunningham dive into the shifting landscape of American musicals. They explore the enduring appeal of 'Wicked,' reflecting on its legacy and emotional depth. The trio compares it to other innovative works like 'Emilia Pérez' and 'Joker: Folie à Deux,' discussing how nostalgia meets modern storytelling. They also analyze the evolution of musicals, from the early 20th century to today's complexities, highlighting the importance of heightened realism and the emotional connections forged through music.

Rashid Khalidi, a professor emeritus at Columbia University and author of "The Hundred Years' War on Palestine," discusses the evolving Palestinian cause amid shifting Middle East dynamics. He critiques the limited support for Palestine from nations like Iran, emphasizing their self-interest. Khalidi also delves into the concept of settler colonialism, asserting it’s an accurate historical description of Israel’s actions, rather than an antisemitic slur. He highlights the complexities of the Israeli-Palestinian conflict and the need for justice and equality to achieve lasting peace.

Audra McDonald shares her journey portraying Rose in 'Gypsy,' exploring the significance of race in casting and her experiences as a Black actress in Broadway. She reflects on the therapeutic role of theater during her childhood and the influence of her family on her artistry. The conversation touches on the challenges of colorblind casting and the emotional complexities of balancing a performing career with motherhood, all while highlighting her deep connection to the iconic music of Stephen Sondheim.

Jonathan Blitzer, a Staff writer at The New Yorker and author of "Everyone Who Is Gone Is Here," dives into the ramifications of Donald Trump's mass-deportation plans. He discusses the chilling rhetoric surrounding immigration and details the potential shift in I.C.E. policies that may transform schools and hospitals into places of fear. Blitzer warns about the unprecedented territory the new administration could enter, highlighting the push to create terror as a tactic. He also draws historical parallels to past immigration enforcement and its impact on communities.

In a thought-provoking conversation, film critic Justin Chang from The New Yorker shares his picks for holiday movie viewing that lean towards the serious side. He dives into gripping tales like 'Nickel Boys,' adapted from Colson Whitehead’s novel, and highlights the haunting 'The Brutalist' featuring Adrien Brody, along with Mike Leigh's impactful 'Hard Truths.' Chang challenges the notion that holiday films must be light, quoting Roger Ebert to reinforce that meaningful storytelling surpasses superficial joy.

Larissa FastHorse, a groundbreaking Lakota playwright and the first Native American woman to have a play on Broadway, discusses her thought-provoking work 'The Thanksgiving Play.' She reflects on her journey of navigating her Indigenous identity and the complexities of representing Native narratives in theater. Meanwhile, author Ayelet Waldman shares her therapeutic experience with quilting as a coping mechanism for stress, emphasizing how it brings her solace during tough times. Both guests intertwine art with personal healing in powerful ways.

Sarah McBride, the first transgender person elected to Congress, shares her journey as a groundbreaking activist and former Delaware State Senator. She discusses the political hostilities she faces, including divisive bathroom bills and misunderstandings of trans identity. McBride emphasizes the importance of turning political rhetoric towards inclusivity and understanding while addressing real issues in her constituency. As she prepares to take her seat, she reflects on her commitment to advocacy amid challenges, striving to inspire hope within the community.

Ketanji Brown Jackson, appointed by President Biden in 2022, shares her groundbreaking journey as the first Black woman on the Supreme Court. She discusses the challenges of navigating a court marked by heightened ethical scrutiny and declining public trust. Jackson reflects on her powerful dissent on affirmative action, emphasizing the importance of accountability. She reveals the collegial culture among justices, contrasting the tension with their camaraderie, and offers insights from her memoir "Lovely One," reflecting on her family and personal growth.

In this conversation, Danielle Deadwyler, known for her powerful role as Emmett Till's mother in 'Till,' discusses her new role in 'The Piano Lesson,' an August Wilson masterpiece. She delves into the conflict between siblings over a family heirloom, exploring themes of heritage, identity, and emotional connections. Deadwyler reflects on the importance of shared histories through struggle and joy, while also addressing the representation of Black women in theater. With Denzel Washington's involvement in adapting Wilson's works, the cultural significance of this art form is emphasized.

Steven Levitsky and Daniel Ziblatt, both Harvard professors and co-authors of "How Democracies Die," dive into the concerning state of American democracy. They argue that voters aren't solely responsible for protecting democracy; it’s the role of elites and institutions. The duo highlights the troubling trend of democratic backsliding, emphasizing that this crisis predates Trump. They stress the need to confront hard questions about political behavior and the Electoral College, warning that without reform, the democratic landscape will continue to deteriorate.