85 episodes
Tangled in 'The Jellicle Ball,' Rosie O'Donnell & 'Deviant' Thoughts (with Sydney James Harcourt)
15/09/2026 | 59 mins.Broadway start Sydney James Harcourt shares his inspiring journey from Detroit to Broadway, his experiences with identity, community, and his new single, ‘Deviant.” Sydney also gets candid about coming out, bullying, and building community. He also shares his emotional experience getting to know Rosie O’Donnell, appearing on ‘Jimmy Kimmel,’ and how he’s navigating a massive wave of attention.
Chapters
Detroit upbringing
Family influence and early dreams of music and theatre
Pursuing the arts and taking risks
Identity and coming out
Overcoming bullying and finding confidence in adulthood
Past and current crushes
The club scene, voguing, and nightlife in New York
Broadway roles: ‘American Idiot,’ ‘Girl from North Country’, ‘Hamilton’
‘Cats: The Jellicle Ball’
The final performance of Cats and its emotional significance
Meeting Rosie O'Donnell and the Jimmy Kimmel appearance
Inspiration behind ‘Deviant’ music- Brian Sims shares his journey from a military family and college football star to a dedicated LGBTQIA+ advocate and politician. He discusses early awareness of his sexuality, the importance of community, and the ongoing fight for civil rights and representation. Brian also gets candid about body image, the bear community, and his hopes and fears for the upcoming election.
Chapters
Early life and military family background
Journey of self-discovery and coming out at 22
The role of community and representation
His work in politics and civil rights advocacy
The importance of education and local activism
His experience with HIV/AIDS history and activism
The impact of media and role models like Wilson Cruz
Fitness journey and identity as a bear
The significance of the Nasty Pig photo shoot
Current political challenges and hope for the future
Tangles - Evan Mulrooney joins Kyle to discuss his upbringing in Delaware, exploring his identity, navigating body image issues, and embracing his authentic self through comedy, acting, and self-deprecation. Evan also offers insights into navigating masculinity, sexuality, and self-acceptance with humor and honesty.
Chapters
Evan's upbringing in Wilmington, Delaware
His journey with body image and big morphia
Exploration of sexuality and pansexual identity
Impact of football culture and toxic masculinity
Transition from sports to comedy and acting
The role of humor in caregiving and community
Experiences with mental health and self-acceptance
Insights into LGBTQIA+ identity and societal perceptions
Creative pursuits: acting, comedy, writing
Hope and resilience in challenging times
Tangles Tangled in Irish Roots, Body Neutrality & Being a Disney Adult (with Maggie Winters)
25/08/2026 | 50 mins.Comedian Maggie Winters shares her journey to stand-up success, her creative process for her special “Marguerite,” and her thoughts on comedy, body neutrality, and navigating the industry. Follow Maggie on Instagram and watch her special on YouTube.
Chapters
Workshopping a stand-up special
Growing up Irish and the desire for attention
Deciding to pursue full-time comedy
Life on the road and maintaining routines
Embracing divisiveness and authenticity in comedy
Community of comedians and influences
Inspiring stand-up specials
Sandwich artist
Being a Disney adult
Body neutrality versus body positivity
Navigating politics and comedy communities
Podcast origins and memorable episodes
Deciding to speak about being single and bisexual
Using social media for comedy and content creation
Developing a new hour and working on material
TanglesTangled in Being a 'Terrible, Horrible, No Good, Very Bad Gay' (with Eliot Glazer)
18/08/2026 | 59 mins.Comedian and author Eliot Glazer joins Kyle to discuss his new book of essays, “The Terrible, Horrible, No Good, Very Bad Gay.” The two explore themes of identity, community, and representation within the LGBTQIA+ experience, as well as the impact of the internet on queer identity and the challenges of navigating labels and body image. The conversation also touches on the dynamics of the “Queer Eye” phenomenon and personal growth in the face of societal expectations. Eliot also discusses the nuances of queer representation, the dynamics between gay men and lesbians, and the cultural significance of shows like “The Golden Girls.” He also shares his thoughts on the phenomenon of bachelorette parties in gay spaces and his love for “The View” and Howard Stern.
Chapters
Minority identity within the LGBTQIA+ community
The internet’s role in queer connection and isolation
The lifelong search for community
Media representation and the formation of self-identity
Labels within the LGBTQIA+ experience
Body image and societal standards in gay culture
The impact and legacy of “Queer Eye”
Personal growth and internalized self-loathing
Self-acceptance and the importance of community
Dorothy, “The Golden Girls,” and queer identification
Queer history and generational understanding
Kindness, rejection, and emotional responsibility
Bachelorette parties and the politics of gay spaces
The cultural influence of “The View”
Anti-Semitism, identity, and belonging
Tangles
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About The Tangle with Kyle Ridley
I’m Kyle, a former morning show producer who spent a decade researching and booking guests, and prepping my anchors to interview them. Of course, there’s only so much that can be said in a 5-minute TV segment, and so many questions go unasked.Now I’m away from the control room and ready to take the mic, speaking with those who fascinate, inspire and challenge me. And the best part: there’s no commercial to cut to when we the dish gets good!I’ll be joined by my best friends and some special guests you might know along the way. We’re diving in deep and swimming in the shallow, so there’s something for everyone. Join me as we rant, rave and ramble through the tangled webs of life, love, loss and so much more! Subscribe now!
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