Comparing Biggie to JAY-Z, Smith shares insights on why he believes the iconic rapper could have reached similar heights if fate had allowed. 

In a departure from his usual sports-centric discussions, Stephen A. Smith, the charismatic host of ESPN's "First Take," recently ventured into the realm of music during an appearance on the "Connect the Dots" podcast. Amidst a bracket challenge ranking the greatest MCs of all time, Smith weighed in on the enduring legacy of the legendary Notorious B.I.G.

Smith's journey through the bracket led him to a pivotal choice between two rap titans: Biggie versus JAY-Z. After deliberation, he speculated on where Biggie might be today if tragedy hadn't cut his life short. "If Biggie were alive today, I think he could be Hov," Smith mused, drawing parallels between the two iconic artists. While ultimately siding with JAY-Z in his final selection, Smith acknowledged Biggie's undeniable impact on hip-hop culture.

Throughout the discussion, Smith highlighted the distinct qualities that set JAY-Z apart, emphasizing his extensive experience and lyrical depth. "JAY-Z knows more. Jay is more seasoned, so he had more to say," Smith remarked, underscoring the rapper's longevity and influence.

Beyond his analysis of rap prowess, Smith shared anecdotes from his interactions with music moguls like JAY-Z, offering a glimpse into the behind-the-scenes dynamics of the industry. Reflecting on a phone call with the rap icon regarding previous remarks on Beyoncé and Rihanna, Smith recounted JAY-Z's candid response and the valuable lessons learned from navigating celebrity relationships.

In hindsight, Smith recognized the nuances of celebrity interactions and the importance of diplomacy in his role as a commentator. "In other words, it’s a business, it’s a part of it, you don’t know how she’ll receive it, etc., etc., etc. That’s all he had to say. I appreciated that," Smith reflected, acknowledging the complexities of balancing personal opinions with professional relationships in the entertainment sphere.

As Stephen A. Smith continues to engage with diverse topics, his foray into the world of hip-hop offers fans a unique perspective on the intersection of sports, entertainment, and culture. Through his insights, Smith bridges the gap between sports commentary and music discourse, showcasing the multifaceted nature of his expertise and influence.