What happens when one of the most influential cultural forces of the last 40 years walks into The Stiletto Room? Baby, you get Flavor Flav — rapper, Rock & Roll Hall of Fame inductee, icon, activist, reality TV pioneer, and one of the realest humans alive.

And let me be clear: Flav isn’t just America’s hype man — he’s an American treasure. A living, breathing reminder of what it looks like to turn survival into joy, pain into purpose, and personality into pure cultural impact.

In this electrifying, emotional, hilarious, historic conversation, I sit down with Flav as he takes us from Public Enemy’s early days and his brotherhood with Chuck D, to grief and legacy, to watching politics shift from “fun” to “dangerous.” We talk Ruby Bridges, civil rights, community impact, and yes — Flav sponsoring the U.S. Olympic water polo team (and getting in the pool himself).

Then we go deep: sobriety, relapse, honesty, redemption. Flav opens up about his mom, his guardian angels, and why secrets keep people stuck — and how telling the truth is what sets you free.

And of course… the Taylor Swift era. The friendship bracelets. The “King Swifty” coronation. The kids losing their minds when they see him.

This episode is history, humor, heart, and healing wrapped in a clock the size of a dinner plate. Flavor Flav isn’t just a legend — he’s a lesson in survival, joy, and pure authenticity.

Expect big laughs, real vulnerability, and a reminder that icons aren’t made by perfection—icons are made by impact. Yeah boyyyyy!

About Flavor Flav

Flavor Flav is the most iconic hype man in history and one of the most recognizable legends in entertainment. A musical prodigy proficient in 15 instruments, he rose to fame in the late ’80s as a co-founder of the legendary hip-hop group Public Enemy. Possessing one of the most sampled voices in hip-hop history, Flav and Public Enemy were inducted into the Rock and Roll Hall of Fame in 2013 and received a Lifetime Achievement Award at the 62nd GRAMMY Awards in 2020. Beyond music, Flav became a reality TV phenomenon with Flavor of Love, VH1’s highest-rated show of all time and a defining pop-culture milestone of the era. In 2024, he made headlines worldwide as the first individual to sponsor a U.S. Olympic team, serving as official sponsor and hype man for the men’s and women’s water polo teams through the 2028 Los Angeles Olympics. He continues to use his platform to advocate for mental health, sobriety, humanitarian rights, and women’s sports, inspiring audiences across generations worldwide.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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What happens when one of your closest friends — and one of the most fearless humans you know — sits down in The Stiletto Room? You get Chaz Bono, baby. Actor, activist, producer, trailblazer, and someone I’ve walked through sobriety, transformation, and truth with for decades.

In this raw, powerful, beautifully honest conversation, Chaz opens up about growing up as the child of Sonny & Cher, navigating identity long before the world had language for it, and what it really took to step into himself at 40 years old. We talk about transition, chosen family, the brutal political climate, LGBTQ+ rights, the fear and freedom of hormones, and how activism becomes a lifeline — not a choice.

Chaz shares how acting saved him, how independent horror became his unexpected creative playground, and why living authentically at ANY age is not just possible — it’s non-negotiable.

This episode is for anyone who’s ever felt “different,” anyone who’s ever had to fight for their place in the world, and anyone who believes in living boldly, bravely, and unapologetically.

About Chaz Bono

Chaz Bono is an American character actor and activist, and the only child of famed entertainers Sonny and Cher. He is best known for his work on American Horror Story and Curb Your Enthusiasm. An acclaimed author, Bono has written three books, including NY Times Best Sellers, Family Outing 1998, and Transition published by Dutton in 2011, a candid account of a forty-year struggle to match his gender identity. Adding to his multiple hyphenated talents, he has shared his life and experiences in, and produced the three-time Emmy nominated documentary, "Becoming Chaz."Bono has a rich history of advocating for LGBTQ rights, having worked for two national LGBTQ organizations, and as public speaker on college campuses and at events around the world. He continues to be a strong voice the for LGBTQ community, and is a passionate champion of equality for all Americans, especially those discriminated against and targeted because of race, religion, sex, age, ethnicity, sexual orientation, and gender identity. In 2012 Bono decided to pursue his lifelong dream to have a career as a character actor. He’s guest stared in the films Dirty, Reborn, Three From Hell, Reboot Camp, The Bell Keeper, and Burry The Bride and Little Bites, which he also produced. Bono has also guest starred on American Horror Story: Roanoke and American Horror Story: Cult, Curb Your Enthusiasm, The Bold and the Beautiful.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
https://a.co/d/6sGKcer

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There are artists… and then there are American treasures. And today in The Stiletto Room, I sit down with one of the women who shaped my entire life: Melissa Etheridge.

When I tell you her first album catapulted me into my identity, my career, my purpose — baby, that is not an exaggeration. Melissa talks about writing every song herself, getting discovered in a Long Beach women’s bar, breaking through a male-dominated industry, and the moment she realized her authenticity was her superpower long before the world was ready for it.

We talk Grammys, Oscars, touring overseas, her iconic Janis Joplin performance at the Grammys while she was still in cancer treatment, and the spiritual awakening that reshaped her entire life. Melissa opens up about manifesting her dreams — including her new album Rise, her duet with Chris Stapleton, and the foundation she created in honor of her son to revolutionize addiction treatment.

This conversation is about music, resilience, motherhood, activism, joy, and the wild courage it takes to stay authentic for four decades.

Melissa Etheridge doesn’t just inspire — she changes lives. Mine included.

ABOUT MELISSA ETHERIDGE:

Melissa Etheridge is a Grammy- and Oscar-winning rock icon celebrated for her unmistakable vocals, confessional songwriting, and decades of fearless authenticity. She broke through in 1988 with her self-titled debut and became a defining voice of American rock with hits like “Bring Me Some Water,” “Ain’t It Heavy,” “I’m the Only One,” and the Grammy-winning “Come to My Window.”

Her landmark albums Yes I Am and Your Little Secret cemented her place in music history, earning her ASCAP’s Songwriter of the Year. In 2007, she won an Academy Award for “I Need to Wake Up,” written for An Inconvenient Truth. Etheridge has long been a pioneer in LGBTQ+ visibility and cultural impact, famously performing bald at the 2005 Grammys during cancer treatment — a moment that inspired millions.

She’s continued to evolve with acclaimed projects like Memphis Rock & Soul, The Medicine Show, and One Way Out. Her powerful solo show My Window debuted Off-Broadway before opening on Broadway in 2023 to critical praise.

In 2020, she founded The Etheridge Foundation to advance research and compassionate solutions for opioid use disorder. Her 2024 docuseries and live album I’m Not Broken, recorded inside the Topeka Correctional Facility, showcases the profound healing power of music, storytelling, and

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
https://a.co/d/6sGKcer

Follow The Stiletto Room:
YouTube: https://www.youtube.com/@TheStilettoRoom
The Podcast: https://dinalapolt.komi.io
Instagram: https://www.instagram.com/stilettoroom
TikTok: https://www.tiktok.com/@stilettor00m
X: https://x.com/stilettoroom

Follow Street Smart:
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