Sebastian Stan, an Oscar-nominated actor for his role as Donald Trump, reflects on his journey from Romania to Hollywood. He shares vivid memories of growing up during the fall of communism and his father's influence on his pursuit of the American Dream. Stan discusses the emotional highs and lows of awards season, emphasizing personal growth over accolades. He also reflects on the challenges and triumphs of adapting to new cultures and the sacrifices made by his family, all while navigating the complexities of his acting career.

Questlove, co-founder of The Roots and acclaimed filmmaker, dives deep into the life of Sly Stone and the groundbreaking sound of Sly and the Family Stone. They discuss Sly's innovative blend of genres and the cultural significance of tracks like 'Dance to the Music.' Questlove reflects on the pressures faced by black artists, exploring themes of identity, vulnerability, and mental health in their creative expressions. He sheds light on the emotional complexities in Sly's music, as well as the ordinary life he leads today, all while promoting his new documentary, 'Sly Lives!.'

Ariana Grande, a talented singer and actress acclaimed for her Oscar-nominated role in Wicked, discusses the film's profound themes of belonging and morality. She reflects on her journey as a theater nerd, preparing to embody Galinda. Meanwhile, writer Brittany Newell, a professional dominatrix, dives into her novel 'Soft Core', revealing the hidden world of San Francisco's nightlife and BDSM culture. The conversation explores deep human connections, the struggles of identity, and the emotional intricacies in both performance and personal narratives.

Marianne Faithfull, the iconic British singer and actress, discusses her legendary career, from her breakout hit 'As Tears Go By' to her tumultuous relationship with Mick Jagger. She opens up about her battles with addiction, the transformation of her voice over the years, and the interplay between her public image and true self. Faithfull also reflects on the nostalgia of the 1960s music scene, her family's history during wartime, and the profound impact she leaves on music and culture—all while paying tribute to her incredible legacy.

Brittany Newell, an author and professional dominatrix, shares her journey from writing her first novel at 21 to creating the emotionally rich narrative in 'Softcore.' She discusses how empathy and curiosity shape both her writing and her work in BDSM. The conversation explores the true nature of BDSM spaces, challenging common stereotypes, and touches on the emotional intricacies between dominatrixes and clients. Also, Maureen Corrigan reviews two quintessential New York books, highlighting the city's literary landscape.

Dexter Filkins, a staff writer for The New Yorker and expert on Middle Eastern affairs, delves into Trump's controversial Gaza proposal that envisions displacing Palestinians and U.S. reconstruction. He discusses the geopolitical complexities of the region, analyzing the implications of ongoing violence and failed diplomacy. The conversation also highlights the alarming recruitment crisis in the U.S. military, questioning operational readiness amid changing societal values and potential barriers for new enlistees.

Ariana Grande, an acclaimed actress and singer known for her role as Glinda in 'Wicked,' chats with Tonya Mosley about her journey through music and theater. She fondly recalls singing karaoke with her family and the influence of iconic vocalists like Whitney and Mariah. Grande discusses the joy and challenges of auditioning for 'Wicked' and the importance of mentorship. She shares insights into the emotional authenticity of live singing and highlights the empowering community found in the world of theater.

Sarah Wildman, a New York Times Opinion writer and editor, shares her heart-wrenching journey of parenting her daughter Orli, who battled terminal cancer until age 14. She discusses the emotional turmoil of navigating treatment, the impact of illness on family dynamics, and the deep conversations about life and loss with her daughter. Wildman reflects on cultural attitudes towards death and explores Jewish mourning practices, illustrating the chaos of losing a child while balancing a demanding career. Her insights on grief and resilience are both poignant and profound.

Ahmir "Questlove" Thompson, co-director of the documentary about SNL's musical legacy and The Roots co-founder, discusses the cultural impact of the show over 50 years. Imani Perry, author and Harvard professor, dives into her book "Black and Blues," revealing the significance of the color blue in Black life and its connection to blues music. David Bianculli adds insights as a TV critic, highlighting the profound emotional resonance of SNL's performances and their influence on music history, identity, and creativity.

Adam Scott, known for his roles in Parks and Recreation and Big Little Lies, dives into the thought-provoking themes of his Apple TV+ series Severance. He discusses the emotional complexity of work-life separation and shares personal reflections on grief and creativity in a post-pandemic world. Scott highlights the joys and challenges of shifting between drama and comedy, especially through his experiences on Party Down. The conversation also touches on career-defining moments, illustrating the deep connections between personal narratives and artistic expression.