This week, writer/comedian Naomi Ekperigin deep dives into her multifaceted career. Naomi and Kyle discuss her early influences, the evolution of her comedy career, and the impact of the pandemic on her work. She reflects on the challenges of navigating the comedy scene, the role of social media, and her commitment to safety in public spaces. Naomi also delves into her experiences with marriage, pets, and finding hope in difficult times. She also talks about her work on “Broad City,” “Mythic Quest,” “St. Denis Medical,” and her weekly podcast, “Couples Therapy.”

Chapters

• A performer through and through
• Improv journey
• 90’s entertainment and iconic Black television
• The art of standup
• The pandemic’s impact on her work
• Writing for television
• Social media in comedy
• Dog momma
• Her pets have taught her about love and responsibility
• Hope in dark times
• Current tangles
• Rapid fire reflections

This week, Tom Arnold reflects on his extensive career in the entertainment industry, sharing insights about his journey through stand-up comedy, four ex-wives, fatherhood and sobriety. He discusses the evolution of comedy over the decades, his experiences with fame, and the legacy of the groundbreaking show 'Roseanne.' Tom also shares details about his directorial debut, 'The Breakup Pill,' and emphasizes the importance of resilience and humor in navigating life's challenges. Catch Tom on his ‘My Crazy X-Wife’ tour across the country.

Chapters

• Resilience in the entertainment industry
• Stand-up comedy through the decades
• ‘My Crazy X-Wife’ tour
• Life lessons from fatherhood and divorces
• Politics, comedy and Trump
• The ‘Roseanne’ years
• Directorial debut

Kicking off 2026, Candiace Dillard Bassett joins Kyle for a wide-ranging and candid conversation. Candiace discusses her experiences as a new mom, her participation in season four of “The Traitors,” and her upcoming music projects. She also reflects on the challenges of reality TV, the importance of authenticity, and her advocacy for the LGBTQ+ community. We also get tangled in “The Real Housewives of Potomac,” the fifth anniversary of “Deep Space,” and her harrowing postpartum experience.

Chapters

• Returning to reality TV
• “The Traitors” season four
• Friendships in “The Traitors” castle
• Reality TV: authenticity vs. drama
• “Deep Space” anniversary
• New music in the works
• Motherhood and postpartum emergency
• Embracing the LGBTQ+ community
• Reflections on RHOP
• Current tangles

Culture and entertainment writer H. Alan Scott has a true tangle with Kyle, discussing the highs and lows of life. H. Alan shares his personal journey from Mormonism to Judaism, his experiences with cancer, and his lifelong love of all this pop culture. H. Alan shares his childhood influences, all-time favorite shows, standout interviews, and his Oscar predictions. The conversation also delves into celebrity crushes and the challenges of the entertainment industry.

Chapters

• Reality TV and comfort viewing
• Religious background
• Surviving cancer
• Childhood inspirations
• Coming out and family dynamics
• Tribute to Diane Keaton
• Latest TV obsessions
• Celebrity crushes
• Memorable interviews
• When interviews go south
• Award predictions

Actress, author and podcaster Jessica St. Clair joins Kyle for a candid conversation on life, career, marriage and friendship. Jessica offers a hilarious and heartfelt look at life’s highs and lows – from landing major TV and film gigs, launching a hit podcast, writing with her best friends, to battling cancer and then caring for her husband in the wake of his diagnosis. Jessica also discusses the profound impact of her experiences and her unbreakable spirit.

Chapters

• The early years
• Finding comedic voice
• Navigating Hollywood
• Writing and performing comedy
• The power of female friendships
• “Best Friends Forever” and “Playing House”
• Recalibrating life after a cancer diagnosis
• A new chapter in Londo
• The impact of Covid
• Evolution of “The Deep Dive” podcast
• “The Art of Small Talk”
• Memoir in process
• Current tangles
• Rapid fire reflections

Kyle is joined by singer-songwriter Morgan Karr (MORGXN), who shares his journey from Nashville to Los Angeles and back, exploring themes of identity, love, loss, and resilience. He discusses the impact of his southern upbringing, coming out, and the importance of finding role models and supporters in the LGBTQ+ community. MORGXN also reflects on his experience in Broadway’s “Spring Awakening,” his songwriting process, and the healing power of pets. He emphasizes the significance of hope in his music and the need for inclusivity in holiday songs.

Chapters

• Nashville upbringing
• Religious trauma in the South
• Finding role models in the LGBTQ+ community
• Broadway experiences
• Songwriting to express personal truths
• The life-changing power of pets
• Creating meaningful music videos
• Nashville’s melting pot of talent
• The Heartland EPs
• Themes of resilience and hope for the queer community
• Inclusivity in holiday music
• Current tangles

This week, Kyle is joined by comedian-author-actress-entrepreneur Phoebe Robinson! The trailblazer reflects on her journey from aspiring writer to a prominent figure in comedy and publishing. She also discusses her comedic influences, the evolution of the comedy landscape, and her experience launching the imprint, Tiny Reparations Books. Robinson shares insights on personal growth, the challenges of balancing work and life, and her new special, 'I Don't Wanna Work Anymore.' The discussion also touches on the impact of social media, the importance of authenticity in comedy, and her views on relationships and self-worth.

Chapters

• Ohio upbringing and comedic north stars
• The divisive state of comedy
• The writing journey
• Love of books and launching an imprint
• Crafting a special
• “I Don’t Wanna Work Anymore”
• Pushing boundaries
• Growth from 30 to 40
• Exhaustion of the 'girl boss' mentality
• Becoming a marathon runner
• Current tangles
• Rapid fire reflections

This week Kyle is joined by comedian, podcaster and actress Liza Treyger! They discuss her recent European tour, childhood influences, and the impact of television on her career. Liza reflects on the evolution of comedy in the age of social media, her unique performance style, and the current state of the comedy scene, particularly regarding political commentary and the wave of ‘bro’ podcasters. Liza also shares her passion for true crime cases, her ultimate dreams, and her love for Taylor Swift.

Chapters

• European tour
• Childhood and early influences
• From open mics to headlining
• Netflix special
• Crafting material
• The state of comedy
• Political comedy and podcasting
• Women in comedy
• Censorship and free speech
• Creative control and personal ambitions
• Future projects
• True crime fascination
• Taylor Swift tangle