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Big Daddy Kane — hip-hop pioneer, Grammy-winning MC, and one of Brooklyn’s finest — sits down with Shannon Sharpe at Club Shay Shay for an in-depth conversation on his 40-year journey in the culture, from early block parties to influencing some of the biggest artists of all time.

Kane opens up about his roots in Brooklyn, discovering hip-hop through legends like DJ Kool Herc, Melle Mel, Afrika Bambaataa, and Grandmaster Flash, and finding his voice in the early 1980s. He recalls hearing kids rhyme on the block, crafting his first slick lines from hustler slang, and eventually linking with Biz Markie, the man who gave him his first big break. From battling in the streets to recording demos no one heard, Kane explains how persistence turned him into one of rap’s sharpest lyricists.

He reflects on the next wave of Brooklyn talent — Biggie, Jay-Z, Lil’ Kim, Foxy Brown, Mos Def, Busta Rhymes, Joey Bada$$, and Pop Smoke — and how the streets shaped their stories. Kane shares memories of having Biggie and Tupac freestyle at Madison Square Garden, his friendship with Pac dating back to Digital Underground, and why he believes Biggie could’ve been the greatest MC and Pac the “Michael Jackson of hip-hop” if they had lived longer.

The conversation moves into the industry’s highs and lows: lines wrapped around the corner for vinyl releases, the frustration of streaming payouts today, and how fast-food culture has replaced patience and truth in music. Kane talks about turning down Suge Knight’s $1 million Death Row East offer, performing alongside Bobby Brown, and how collaborations with artists like Quincy Jones, Tito Jackson, Wu-Tang Clan, and Madonna gave him some of his most unforgettable experiences.

As hip-hop evolved, Kane watched the role of freestyle, lyricism, and beef change. He looks back at battles like LL Cool J vs. Kool Moe Dee and compares them to today’s Drake vs. Kendrick Lamar, pointing out how competition sharpens MCs but can hurt careers if it spills into reality. He also breaks down why artists like Rakim, J. Cole, Kendrick Lamar, Lady London, Conway the Machine, and Benny the Butcher keep the spirit of lyricism alive.

Kane doesn’t shy away from bigger reflections either — from fashion’s roots in Black culture, to working with icons like Marvin Gaye, Patti LaBelle, Luther Vandross, Ray Charles, and Miles Davis. He explains why his Grammy isn’t on display, why fan appreciation means more than trophies, and how hip-hop grew from neighborhood block parties into global festivals.

Finally, Kane shares his perspective on the next 50 years of the culture. He wants to see young artists who write songs that impact lives, who give unforgettable performances, and who respect the generation that paved the way. From freestyling with Pac and Biggie to mentoring today’s lyricists, Big Daddy Kane delivers rare stories, sharp insight, and a masterclass on what it really means to be an MC — and what it takes to last in hip-hop.

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