The Tangle with Kyle Ridley

This week, Kyle is joined by journalist, social media pro and his former colleague Jeannette Reyes. She shares her journey from aspiring attorney to successful journalist and social media personality. Jeannette reflects on her standout moments in journalism, the challenges of the industry, and her transition to a more flexible career that allows her to embrace motherhood and personal growth. Jeannette discusses the importance of cu...

This week, celebrated actor and host Jerry O’Connell speaks with Kyle about the 'Stand By Me' 40th anniversary tour with castmates Corey Feldman and Wil Wheaton. Jerry reflects on the iconic movie, which he filmed at just 11 years old. He also shares his grief in the wake of director Rob Reiner’s passing and gets candid about hitting a professional peak as a child. 

Chapters 

• Remembering Rob Reiner
• The joy of reunion and...

This week, renowned podcaster Ben Mandelker discusses his rise in the podcasting ranks with “Watch What Crappens,” where he deep dives into Bravo’s countless reality shows. The conversation also covers Ben’s early influences, coming out, celebrity north stars, “The Real Housewives” franchises, and the dynamics of the podcasting community.

Chapters

• Childhood influences and early interests
• Coming out
• SNL and comedic influences 
• Realit...

This week, screenwriter and producer Jonathan Hurwitz shares his journey through coming out in small-town Maryland, to moving to New York City and Los Angeles for a career in entertainment. We discus his work on the “Lizzie McGuire” reboot that never made it to air, as well as his dating life, hookup apps, and pivoting in your 30s. 

Chapters 

• Maryland upbringing and family support
• Moving to New York and Hollywood 
• Working in animat...

This week, actor-director Tony Goldwyn joins Kyle to discuss co-directing “Chez Joey,” now playing at Arena Stage in Washington, DC. The show is choreographed by Savion Glover, stars Tony winner Myles Frost, and explores themes of love, jazz, community, and artistic expression. Tony reflects on the challenges and rewards of bringing the show to life, the importance of storytelling, and the impact of art in bridging divides in socie...

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 importa...

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 ...

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 narra...

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 sh...

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 ...

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 als...

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 offe...

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 ...

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 i...

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 anniversar...

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 challen...

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...

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 heal...

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...