Blocks w/ Neal Brennan

Jordan Klepper, comedian and former Daily Show correspondent, talks reporting from MAGA events and being on the ground at January 6. He breaks down making field pieces, bringing a Trump fan to a Kamala rally, touring road life and travel habits, balancing hosting pressures with parenting, and shifting from smug atheism toward agnostic curiosity.

Ali Siddiq, a stand-up comedian and storyteller known for autobiographical specials, shares a life shaped by selling drugs, incarceration, and deep family loss. He talks about growing up in poverty, the sting that led to arrest, surviving prison culture, and how grief and fatherhood reshaped him. He also explains finding his storytelling voice and turning turbulence into comedy.

Sarah Sherman (aka Sarah Squirm), comedian and performer known for her surreal, body-horror–tinged style and HBO special Live & In The Flesh. She talks about her distinctive fashion and stage look. She digs into lifelong anxiety, SNL nightmares, and therapy. She explores feeling ‘kind of bad at standup,’ live sketches versus pre-taped work, touring challenges, the internet’s pressure, and embracing grossness.

Sam Harris, philosopher of mind and neuroscientist known for Making Sense and Waking Up. He talks about meditation and spiritual charisma, including retreats and skeptical views on psychic claims. He explores balancing contemplative practice with political engagement, social media’s harms, Trumpism and leftist hypocrisy, plus reflections on family and writing ambitions.

Kevin Nealon, actor and comedian (SNL, Weeds, Happy Gilmore), shares career anecdotes and personal quirks. He talks about living with ADHD and claustrophobia. He recalls late-night TV memories, friendships in comedy, his documentary and art, and how he copes with anxiety and health concerns.

Robby Hoffman, comedian and writer behind the Netflix special Wake Up, discusses her Orthodox upbringing, leaving religion, and growing up poor with nine siblings. She talks about feeling like an outsider, using humor as currency, bold creative risks, and her decision to have top surgery and how it reshaped her identity and daily life.

Phil Hanley, comedian, former male model, and author of Spellbound: My Life as a Dyslexic Wordsmith, talks about living with dyslexia, ADHD, and how those traits shaped his art. He recounts modeling, finding improv, turning personal pain into comedy, and his messy writing and rehearsal routines. He also discusses relationships, coping strategies, and how gratitude reframed his life.

In this engaging conversation, comedian Matt McCusker, co-host of Matt & Shane's Secret Podcast and star of the Netflix special 'A Humble Offering', opens up about the challenges of parenting and the anxiety that often accompanies it. He shares insights on navigating panic attacks, the importance of therapy, and the unexpected emotional shifts brought by fatherhood. Matt also discusses the unique ways men can support partners through their menstrual cycles, along with his experiences with dissociation and personal growth, making for a heartfelt and relatable dialogue.

Hank Azaria, the talented voice behind iconic characters on The Simpsons, dives into his complex journey through career challenges and personal recovery. He reflects on the Apu controversy, his initial confusion, and how he learned about racism and inclusivity. Hank discusses the pressures of perfectionism, workaholism, and how they impacted his life. He shares insights on parenting, the balance of trust and boundaries, and even showcases his impressive impressions, providing a heartfelt look at fame, self-discovery, and connection.

Scott Galloway, a professor and renowned business commentator, dives into his complex relationship with money, masculinity, and education. He discusses his upbringing by a single immigrant mother and the weight of loss on his emotional life. Galloway critiques the elitism in higher education and advocates for progressive tax reforms to address income inequality. He examines men's evolving roles in society, emphasizing mentorship for boys in the absence of positive male figures, and highlights the harmful effects of big tech on social skills and relationship dynamics.