The Tangle with Kyle Ridley

Best-selling author, editor, and former MTV VJ Dave Holmes joins Kyle for a reflective hour on the ‘90s, pre-online dating, tangible media, and much more. Dave offers behind-the-scenes stories from his days at MTV, including dream interviews and placing second on the “Wanna Be a VJ” contest. He gets candid about coming out, celebrity crushes, and hosting the “Homophilia” podcast. Dave also discusses the evolution of music videos, digital media, and the rapid consumption of music instead of a steady rollout. 

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This week, Kyle is joined by Emmy winning host Sherri Shepherd, who shares her journey through comedy, television, and her new “Make it Make Sense” comedy tour. Sherri discusses the evolution of standup, the challenges of social media, her diverse roles, and her closeknit comedy community. She also shares the joys of having her own talk show and the bittersweetness of having it come to an end this year. Get your tickets to Sherri’s tour at sherrishepherd.com.

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This week, Joel Kim Booster opens up about his diverse career in comedy, acting, writing, and producing. He shares insights on his creative process, navigating the industry, and balancing personal life with professional projects, including his work on 'Fire Island' and the new 'Scrubs' revival. Joel also offers a preview of his new standup tour, heading across the country. 

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This week, Kyle is joined by Emmy winning actor, writer and producer Dan Bucatinsky. They discuss the third and final season of “The Comeback,” which is Kyle’s all-time favorite show! Dan shares insights into its creative process and enduring legacy over 21 years. He also offers an inside look at the show's development, Lisa Kudrow's remarkable talents, and the evolving landscape of television. 

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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 cultural representation, maintaining relationships, and the impact of humor in her work. She also highlights her podcasting experience and the value of vulnerability in storytelling, all while navigating the complexities of modern life and...

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. 

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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.

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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. 

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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 society. Additionally, he shares insights on maintaining hope in divisive times and the inspiration behind his podcast with his daughter. Tony also participates in a rapid fire round through his filmography. 

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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...

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. 

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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.

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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.”

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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.” 

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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. 

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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.

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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.” 

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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. 

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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. 

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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.

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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. 

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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. 

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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.

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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. 

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This week, Kyle is joined by actor, musician and improv king Charles Esten! Charles reflects on his journey growing up in Alexandria, Virginia, to becoming a beloved musician and actor, widely known for hit shows ‘Nashville’ and ‘Outer Banks.’ Charles shares insights into his songwriting process, the importance of family, and the healing power of music through his involvement with Musicians On Call. Charles also discusses the joys of performing live, his lasting relationships with co-stars, and his passion for authenticity and connection. Charles covers many more topics including his wide-ranging roles on screen, his upcoming films, ‘Nashville’ reunion tour, turnin...

This week, Kyle is joined by Emmy winner Jane Lynch! The renowned actress, musician and host is heading out on her annual “Swingin’ Little Christmas” tour with friends Kate Flannery and Tim Davis. The tour kicks off Nov. 29 in Bethesda, Maryland, and runs through Dec. 17. In addition to the tour, Jane reflects on her illustrious career and some of her most acclaimed roles, including “Best in Show,” “A Mighty Wind,” and “The 40-Year-Old Virgin.” Jane also gets candid about the massive success of “Glee” and the tragedies that loom over the groundbreaking series. 

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This week, comedian and impressionist Andrea Lopez joins Kyle to share her comedic journey from DC, Los Angeles, to New York City. She discusses her early SNL influences, the importance of mentorship, and the challenges of navigating the entertainment industry. Andrea also reflects on her experiences with rejection, her creative process in developing characters, and honing her impressions. We’re also treated to her hilarious impersonations of Teresa Giudice, Kourtney Kardashian, Jennifer Coolidge, and more.

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This week, Kyle is joined by writer, host, traveler, and foodie extraordinaire Phil Rosenthal. They discuss his new book, “Phil's Favorites: Recipes from Friends and Family to Make at Home,” and his passion for uniting people through food and travel. Phil also reminisces on 30 years of “Everybody Loves Raymond” and his favorite parts of scripted vs. unscripted shows. Phil reflects on the significance of community and laughter, shares insights on the evolution of comedy, and highlights his new diner venture. Phil also emphasizes the joy of food as a connector and the role of diversity in enriching culinary experiences.

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