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