This week, Caroline Rhea joins Kyle to discuss her new tour, standup special, and acting gigs past and present. Caroline shares her standup journey from the late ‘80s to today, in addition to discussing ageism and sexism in comedy. Caroline also reflects on her massive hit “Sabrina the Teenage Witch” and her yearlong talk show in the early 2000s. She shares personal anecdotes about parenting, the challenges of balancing career and family, and her new dramatic series, “Sheriff Country.”

Chapters

• Standup past and present
• Evolution of comedy and female representation
• Parenthood and comedy
• Crafting a set
• Early inspirations
• “Sabrina the Teenage Witch”
• Having a talk show
• New comedy special, “I Identify as a Witch”
• “Sherrif Country”
• Maintaining hope
• Current tangles

This week, comedian Colin Braun joins Kyle to discuss his winding road through engineering, comedy, all the way to Ireland. Colin shares his standup inspirations and what it was like to first get up on stage. He’s also candid about his struggles with depression and the complexities of life as a gay man with ADHD. Colin opens up about his divorce, fears of a fascist government, and his move to Ireland after the 2024 election. He also discusses his analytical approach to comedy, health, salads and much more.

Chapters

• Early inspirations
• Open mic nights
• Analyzing and tracking jokes
• Childhood, depression and ADHD
• Gay marriage, gay divorce
• Leaving the U.S. for Ireland
• Comedy, dating and health care in Ireland
• Self-sufficiency in cooking and health
• All about salads
• Current tangles

Pop star Tiffany joins Kyle to discuss her 40-year career in music and the many ups and downs through the decades. Tiffany shares her journey from a record-breaking teen performer, navigating industry rejection in her 20s, becoming a mom, and finding her sweet spot as a songwriter. She reflects on the lack of sisterhood in the industry in her early ears, and the pressures of being in the public eye at a young age. Tiffany also offers insights on personal growth, the importance of friendship, and her new culinary and holistic projects.

Chapters

• UK life and getting over fears of flying
• The early days and chaotic childhood
• Expression and comfort through poetry
• 80’s pop star and touring malls
• 90’s industry shifts and motherhood
• Embracing songwriting
• Reflections on fame, pressure and loneliness
• Overlap with Alanis Morissette
• “Pop Life” cookbook
• Charity and holistic projects
• Planning a memoir

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