Big Daddy Kane Breaks Down His Legacy, Rap Icons & Industry Truths on Club Shay Shay

Hip hop pioneer Big Daddy Kane joined Shannon Sharpe for a new episode of Club Shay Shay, giving fans one of his most in-depth interviews in recent years. The Brooklyn MC spoke candidly about his early beginnings, his influence on rap’s golden era, and his thoughts on icons like Tupac, Biggie, Jay-Z, LL Cool J, and Kendrick Lamar.

The conversation comes at a time when Kane is trending again — following his live performance in Toronto at Russell Peters’ Old School Mixtape Party (watch on WorldWide Entertainment TV Media).

Kane on Tupac & Biggie

One of the most powerful moments of the interview came when Kane reflected on his relationships with Tupac Shakur and The Notorious B.I.G.

Kane revealed his friendship with Pac stretched back to the Digital Underground days, describing him as having the charisma and energy to become the “Michael Jackson of hip hop.”
On Biggie, Kane believes that if the Brooklyn rapper had lived longer, he might have been recognized as the greatest MC of all time.

On Jay-Z, LL Cool J & Rap Beef Culture

Big Daddy Kane also opened up about his history with Jay-Z, noting moments of support and friction over the years. He compared classic beefs like LL Cool J vs. Kool Moe Dee to modern rivalries such as Kendrick Lamar vs. Drake, arguing that while competition sharpens MCs, it can damage careers when it spills into real life.

Kane also praised artists like J. Cole, Kendrick Lamar, Lady London, Conway the Machine, and Benny the Butcher for keeping lyricism alive in today’s era.

From Vinyl to Streaming

Looking back on the industry’s evolution, Kane spoke about:

The thrill of lines wrapped around the block for vinyl releases.
Turning down a $1 million offer from Suge Knight’s Death Row East.
The frustration of modern streaming payouts, calling it an industry that rewards speed over patience and truth.

Fashion, Legacy & Humility

Big Daddy Kane reminded fans that fashion trends and self-expression in hip hop grew from Black culture and community pride.

Despite winning a Grammy, Kane humbly admitted his trophy isn’t even displayed at home:

“Awards are cool, but fan love means more than trophies.”

Why This Interview Matters

Big Daddy Kane’s Club Shay Shay appearance isn’t just a trip down memory lane. It connects generations: from the block party roots of the 1980s, to the golden age of the 90s, to today’s ongoing battles for authenticity in hip hop.

With his Toronto performance still fresh in fans’ minds and this interview now making waves online, Kane is proving that his voice remains one of the sharpest and most respected in the culture.