The incredible Heather McMahan joins Kyle for the 50th episode of “The Tangle with Kyle Ridley.” The comedic powerhouse reflects on her winding journey to success, the impact of COVID-19 on her career, early influences, and her relentless work ethic. Heather shares her aspirations for the future, including scripted projects and her third comedy special. She also addresses the challenges of navigating public scrutiny and the importance of political commentary in her work, all while maintaining a light-hearted and humorous perspective. Heather discusses the cathartic nature of her podcast, the importance of family, her constant wanderlust, struggles with sleep, and how she maintains hope during challenging times.

Chapters

• Social media success
• The impact of Covid on career
• Comedy roots and influences
• The hustle and work ethic
• Vision boarding
• Comedy landscape
• Politics and outspokenness
• Handling public scrutiny
• New comedy special
• The catharsis of podcasting
• Family and personal growth
• Travel dreams and culinary adventures
• Current tangles
• Hope in dark times

This week, John Hill shares his journey from a conservative Texas upbringing to becoming a prominent figure in the entertainment industry. He discusses the challenges of growing up in a religious household, the impact of bullying, and the importance of finding community through theater. John reflects on the significance of media representation, his career in Broadway and television, and the influences of artists like Tori Amos. He opens up about his sobriety journey, body positivity, and the importance of self-acceptance as he navigates his life and career.

Chapters

• Conservative upbringing
• Navigating bullying and being an outcast
• Coming out and family dynamics
• Reflections on generational differences in the LGBTQIA+ community
• Theatre career and Broadway experiences
• Creative writing and comedy
• Musical influences
• Meeting and dating Andy Cohen
• Celebrity crushes
• Dating life
• Working in reality TV
• The art of interviewing
• Dream guests and starstruck moments
• The “Housewives” phenomenon
• Sobriety journey
• Body-positivity and self-acceptance
• Upcoming book
• Current tangles

Actress and director Lennon Parham shares her journey from Southern roots to becoming a prominent figure in comedy and television. She discusses her early education, the influence of her family, and her transition into the world of improv and writing. Lennon reflects on her deep friendship and creative partnership with Jessica St. Clair, navigating the challenges of the television industry, and the importance of female-driven narratives. She also touches on her experiences directing, balancing motherhood with her career, and her current projects, all while emphasizing the need for comedy in today's world.

Chapters

• Upbringing and early career
• Journey to improv
• Writing and collaborating
• Best friendship with Jessica St. Clair
• Television breakthrough
• Challenges and triumphs
• Directing “Somebody Somewhere”
• Directing vs. acting
• Small talk
• Current tangles
• Rapid fire roles

This week, Tim Bagley shares his journey from a humorous Midwestern upbringing to becoming a prominent figure in comedy and television. He reflects on the challenges of LGBTQ+ representation in Hollywood, his personal experiences with coming out, and the impact of loss and grief on his life and career. Tim also discusses the importance of community, maintaining hope in difficult times, and the significance of his iconic roles in shows like “Will and Grace” and “Somebody Somewhere.”

Chapters

• The early days
• Comedy roots and influences
• The move to Hollywood
• Coming out and career challenges
• The impact of loss and grief
• Finding community
• The power of hope
• “The Comeback” and its legacy
• Working with legends
• The beauty of “Somebody Somewhere”
• Current tangles

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