Blair Socci, a comedian with a background in athletics and a love for poetry, shares her unique journey from sports to stand-up. She delves into how her athletic upbringing shaped her comedy, emphasizing resilience and self-expression. Socci also discusses her recent shift on social media, revealing her evolving relationship with it. Her anecdotes about volleyball reveal the humor in self-discovery and body image while intertwining her rich family history of cultural identity and resilience that adds depth to her comedic voice.

Moon Zappa, an author and daughter of the legendary Frank Zappa, opens up about her new memoir, exploring her complicated family legacy. She discusses the emotional fallout from her upbringing and the pressures of public scrutiny. Amidst past relationship reflections with the host, she shares insights on trauma, identity, and the struggles of growing up in a prominent family. Moon's candidness reveals the importance of communication, mental health, and self-acceptance in navigating the complexities of familial dynamics.

In this conversation, Beth Stelling, a comedian known for weaving personal trauma into her humor, shares her journey from childhood experiences to her Netflix special. She discusses the backlash she faced after opening up about an abusive relationship, revealing the complexities of healing through comedy. Beth also reflects on her Ohio roots and the experience of filming a comedy special in her hometown, embracing both vulnerability and resilience in her craft.

Jimmie Dale Gilmore, the acclaimed singer-songwriter and member of The Flatlanders, chats about his unique journey in music, which took a spiritual detour before his solo career took off in his 40s. He reveals insights into finding enlightenment while shaping Americana music. The conversation breezes through memorable topics like the mouth-watering Texas barbecue, his hearing loss struggles, and collaborations with Dave Alvin. Gilmore also shares tales from his band, emphasizing the deep connections between music, friendship, and personal growth.

Anna Akana, a comedian and actor, discusses her transformative journey from childhood instability to becoming a voice for Asian representation in media through YouTube. She shares her experience with mental health advocacy following her sister's tragic death and how comedy became a tool for navigating grief and difficult emotions. Akana also reflects on the complexities of identity and authenticity in the digital age, emphasizing the healing power of humor in addressing sensitive topics.

Wolfgang Van Halen, son of guitar icon Eddie Van Halen, opens up about the challenges of his legacy in the music industry. He shares how touring shaped his musical direction and helped him overcome online trolling and grief. The conversation touches on mental health, personal growth, and navigating family dynamics in a public eye. Wolfgang reflects on his new album 'Mammoth II' and the importance of emotional expression in music, providing insight into his journey of honoring his father's legacy while carving out his own unique sound.

Clare O'Kane, writer for SpongeBob and SNL, discusses growing up, dealing with depression, chasing artistic dreams, and comedy with Marc Maron during a drive from Cleveland to Detroit. They also touch on shared experiences like shaving their heads and dealing with ailing parents.

Author Shalom Auslander discusses breaking away from family and the concept of 'Feh'. They explore how Feh has impacted human beings, especially Jews, for years, breaking the cycle, the misery caused by the nonstop news cycle, and the importance of self-discovery through writing.

Legendary comedian Bob Newhart discusses his iconic comedy albums, early career struggles, and transition to fame. The podcast explores his unique style, collaborations with Dean Martin, and reflections on comedy legends. Bob shares anecdotes from his comedic journey, TV appearances, and the bravery required in stand-up comedy. Discussions on SNL, Will Ferrell, and unconventional acts make for a hilarious and insightful conversation.

Dan St. Germain opens up about his struggles with sobriety, self-releasing his latest comedy special, and reflections on his career in comedy. The podcast covers topics like addiction, family dynamics, comedy writing, and contemplating a move to Canada for a fresh start.