In this episode of Club Shay Shay, Shannon Sharpe sits down with the legendary Bobby Brown—the original bad boy of R&B, Grammy Award–winning icon, New York Times bestselling author, and chart-topping phenomenon. Bobby dives into founding Bobby Brown Foods with his wife and shares his love for cooking—especially his unbeatable fried chicken. He reflects on whether his kids will follow in his entertainment footsteps and reveals his all-time favorite song he’s written. Bobby breaks down his songwriting process, his dynamic collaborations with producer Teddy Riley, and gives us a front-row seat into the making and legacy of My Prerogative. He even reacts to Britney Spears' controversial remake and opens up about being inspired by icons like Michael Jackson, Prince, Rick James, and Stevie Wonder. He shares the real story behind MC Hammer asking him to wear parachute pants and reveals how New Edition taught Michael Jackson how to moonwalk sideways, reflecting on his favorite memories of the King of Pop. He also weighs in on Chris Brown vs. Usher as Michael Jackson’s closest successor and recounts meeting Usher for the first time. From naming his favorite modern artists—SZA, Tems, Jazmine Sullivan, Anthony Hamilton, Bruno Mars—to addressing the hot debate ("Is R&B dead?"), Bobby keeps it real. He drops his Mount Rushmore of R&B singers (Prince, Michael, Marvin, Stevie), reflects on Don’t Be Cruel selling 12 million copies, and gets candid about streaming's impact on artists, the importance of owning your masters, and surviving fame from a young age. He also opens up about being kicked out of New Edition, how predatory music deals cost him $30 million, and why going solo was the best decision of his career. Bobby names his top four singing groups of all time—Gap Band, Jackson 5, New Edition, and Kool & the Gang—and reveals his best and worst purchases, including the wild story of spending $1 million in a single day. He reflects on the pain of being taken advantage of by family and friends, and the loss of one of his closest friends to gun violence. He also shares the pride of building his own studio—where artists like OutKast recorded. From Donald Trump’s cameo in his “On Our Own” video to his run-ins with the law—including getting arrested for dancing with a fan in Georgia—Bobby tells it all. He talks about working with Martin Lawrence in A Thin Line Between Love and Hate, starring in Two Can Play That Game, and why he regrets turning down a role in Strictly Business with Halle Berry and Tommy Davidson. Bobby looks back fondly on his time on Real Husbands of Hollywood with Kevin Hart, Nick Cannon, and Nelly, and opens up about the intense experience of his reality show with Whitney Houston. He also talks about being shot by an ex-boyfriend of his then-girlfriend—and his romance with Janet Jackson in the '80s. The R&B superstar shares his mission with the Bobbi Kristina Serenity House, a charity created in honor of his late daughter. From the highest highs to the most heartbreaking lows, Bobby Brown proves once again why he’s not just a music icon—he’s a cultural legend. Don’t miss this powerful and unfiltered conversation.

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