Jocking Jay-Z

David Callaghan
4 min readJun 15, 2019

He’s a business, man. Not a businessman.

I have a mixed relationship when it comes to Jay-Z. Not that he’s aware of it, or even remotely affected by my thoughts and feelings towards him as a rapper and individual. He seems to be doing ok without me to be honest.

But it’s hard to find anyone who wouldn’t argue that he is a walking, talking embodiment of the American Dream. It used to be the case, that combined with Beyonce, he was a billy billionaire. Now he doesn’t need the wife, he’s hitting ten figures just fine on his own. And all before the age of 50 (just about).

To think he released his first album at 26, which in rap terms, is an ancient age. And before that, he was turned down by a host of major labels for apparently being ‘terrible’. His Roc-A-Fella records was born out of necessity, not choice, and went on to see Reasonable Doubt classed as one of the best Hip Hop albums of any golden age, of any artist.

From street hustler to Wall Street is no easy feat, but there is no one that has done it quite like Jay-Z. An unbelievably gifted artist and a very shrewd businessman, it’s hard to now picture a young Shawn Corey Carter standing on a Brooklyn street corner drug dealing for a living. When the majority of people probably think he’s only famous for being ‘Beyonce’s husband’ and Alicia Keys sidekick on Empire State of Mind.

To me, he’s always appeared very measured, studied and unbelievably switched on. He sees opportunities and seizes them. You can forget all about his twenty year plus rap career, that’s almost a side piece. He has a stake in Uber for an estimated $70 million, sold his renowned Rocawear clothing line for $204 million back in 2007, has Roc Nation running at a cool $75 million and his streaming service, Tidal, is now worth around $100 million, in just under five years of re-launching it. And these are only a small number of investments to mention.

My back and forth with Jay-Z has never been about his entrepreneurship. For me it’s always all about the beats and bars, and who is going to come out as the best in any battle or track. I used to hear people reply “Jay-Z” at ferocious speed when asked who was the best rapper alive. And it used to annoy me, as I found it so ignorant. “They’re only thinking that as he’s the easy, go-to, mainstream name”, “they don’t have a clue about Hip-Hop”, “they’ve only heard his chart songs”. And at one point, I felt like I was right.

The question I’ve always asked, and of course will never have the answer to, is: where would Jay-Z be right now if Tupac, Big L, and especially Biggie, were still alive?

Would he be the biggest name on the planet? Would he be the best rapper alive? He’s had to deal with years of incessant heckles about ‘bitin’ other rappers lines and lyrics, specifically Biggie’s, and it’s not hard to see that even to this day, Jay-Z is still in awe of the power and knowledge of Christopher Wallace.

I’ve always been of the mindset that if Biggie had carried on, Jay-Z would be nowhere near the level of stature and position he is today. Deep down I think even he knows that. Biggie is probably one of the only artists that could of ever made Golden Age rappers look cheap on a track; think Biggie and Jay-Z on Brooklyn’s Finest, or him and Method Man on The What.

Watch earlier videos of them together and it’s there for all to see. Even though he was older than Biggie, Jay-Z looked up to him. They were friends, and good sparring partners on the mic. It would have been a spectacle to see them taking over the world together, just as they were starting to. But with Tupac gone in 96, Biggie six months later in 97, and Big L murdered in 99, who was left to pick up the pieces?

The path became clear, and Jay-Z ran with it. And he’s still as, if not more so relevant today than he was in Hip Hop’s most revered era. 4:44 is an absolute testament to that.

The last five to ten years have seen him hit immeasurable heights. Dr.Dre, Diddy, and Drake, are his nearest competitors for impact, financial success and influence. But where the old school wave of rappers have almost fallen by the wayside for this new group of Hip Hop listeners, Jay-Z, at 49, has got still everyone wanting and waiting for his next move.

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David Callaghan

Hip Hop ‘till I drop. All things music, lifestyle, fashion. From a Black Country angle.