Simon Rich, a celebrated writer known for his work on 'Man Seeking Woman' and 'SNL,' shares candid thoughts on loneliness and anxiety. He reflects on his childhood and experiences at Harvard, discussing how privilege shapes comedy. Simon also dives into the pressures of performing and the impacts of social media on creativity, all while finding humor in the absurdities of life and work. From hilarious anecdotes to deep insights, his conversation reveals the balance between artistic expression and personal challenges.

Neal Brennan interviews Jake Johnson, known for 'New Girl' and 'Self Reliance' on Hulu. They discuss his struggles with dyslexia, dropping out of high school, parenting challenges, and reflections on his Hollywood career. Johnson also shares insights on personal growth, forgiveness, and finding life purpose.

Neal Brennan interviews Paula Poundstone, a killer comic and NPR panelist, about loneliness, tricky family dynamics, solo parenting, asexuality, quitting drinking, terrible bosses, and personal successes and failures.

Comedian Patton Oswalt discusses loneliness, grief, and personal growth with Neal Brennan. Topics include emotional makeup, parenting, grief over Michelle McNamara's death, meeting Meredith Salinger, evolving in comedy, and the desire for love. They also touch on the true crime industry, changing personal issues, and navigating the showbiz industry while maintaining artistic integrity.

Neal Brennan talks with champion pro wrestler and musician Chris Jericho about overcoming challenges in wrestling, the importance of acceptance, the impact of politics in the industry, and personal growth. They also discuss the parallels between wrestling and other entertainment industries, navigating creativity, and the evolution of the wrestling industry over the years.

Neal Brennan interviews Joel McHale about his journey in showbiz, struggles with dyslexia, and work on 'The Soup' and 'Community'. They discuss parenting, mental health, imposter syndrome, and gratitude, showcasing McHale's humor and personal growth.

Neal Brennan chats with Phil Rosenthal, the creator of 'Somebody Feed Phil' and 'Everybody Loves Raymond,' discussing topics like sitcom writing, travel experiences, dealing with negativity and OCD, meeting David Letterman, and the benefits of forgetting past mistakes and insecurities.

Neal Brennan interviews Darrell Hammond, SNL cast member, discussing his emotionally traumatic life, abusive mother, cutting, and transformative moments like his father apologizing on his deathbed, along with topics of drinking, monsters, and advice.

Neal Brennan interviews comedy legend George Wallace about his career highlights, quirky travel experiences, shopping addiction, hypochondria, and reflections on ageism in show business. From starting standup to his friendship with Jerry Seinfeld, George shares candid stories about fame, wealth, and the importance of leaving a legacy.

Neal Brennan interviews Al Madrigal, comedian known for 'The Daily Show,' about loneliness, ADHD, starting stand-up, coping with grief, struggles with alcohol, social anxiety, and setting priorities. They discuss personal anecdotes, career challenges, and reflections on family dynamics and comedy experiences.