Download the PrizePicks app today and use code SHANNON to get $150 in lineups after you win first $5 lineup! https://prizepicks.onelink.me/LME0/SHANNON  Protect your family with life insurance from Ethos. Get up to $3 million in coverage in as little as 10 minutes at https://ethos.com/shayshay. Application times may vary. Rates may vary. Trustpilot rating as of 8/1/2026. Grammy Award-winning singer and Broadway legend Stephanie Mills joins Club Shay Shay for a conversation about her six-decade career, growing up in Brooklyn, and becoming one of R&B's most iconic voices. Stephanie reflects on winning the Apollo Theater's Amateur Night at just nine years old, performing alongside James Brown, King Curtis, and Roberta Flack, and landing the legendary role of Dorothy in the Broadway musical The Wiz at 17. She opens up about the racial backlash and hate mail she received for playing Dorothy, criticism of her appearance and skin color, and the importance of Black representation on Broadway. Stephanie shares personal stories about her close friendship with Michael Jackson, including meeting him through The Wiz, staying at his apartment, braiding his hair, cooking for him, and why she continues to defend his legacy. She discusses Michael Jackson's ambition to become the King of Pop, his music catalog, his disputes with the music industry, his changing appearance, the Pepsi accident, and the circumstances surrounding his death. She also speaks about Oprah Winfrey, Gayle King, Whitney Houston, Kobe Bryant, R. Kelly, Chris Brown, and why she believes Black celebrities should stand up for one another. She discusses Prince, his battle against the music industry, his famous SLAVE message, and how entertainers can become cash cows for the people around them. She shares her thoughts on streaming, artist ownership, and why she has remained independent. She also reflects on her relationship with Teddy Pendergrass, performing with the Queens of R&B, Chaka Khan, the possibility of a Verzuz rematch, and artists she'd love to collaborate with. Stephanie talks about dating, marriage, infidelity, jealousy, standing up for herself, and the importance of love, respect, honesty, and faith. She opens up about motherhood, raising her son, who has Down syndrome. She discusses her For Love Down Foundation, her upcoming Christmas music project Dear Amanda, her plans to tour in 2027, and her forthcoming book about raising her son. Stephanie also talks about her love for Fat Joe, Tupac, DMX, Rihanna, and Mariah Carey, her family connection to K-Ci & JoJo, her Motown boot camp experience, and the importance of prayer, staying true to herself, and surviving the music business. She closes out by addressing the whitewashing of R&B, racism in radio, and why she believes today's music industry is more challenging for Black artists than ever. See omnystudio.com/listener for privacy information.