For the two decades following Reasonable Doubt, Jay-Z dominated music and culture. During one eight-year period within that stretch, he released eight albums, six of which went to number one. His hit songs and collaborations were omnipresent: “Big Pimpin’,” “99 Problems,” “Crazy in Love,” “Umbrella,” “Empire State of Mind,” “N-ggas in Paris.” With cofounders Dash and Burke, he sold half of Roc-A-Fella Records for a large sum to Def Jam Recordings in 1997, and the other half for a much larger sum seven years later. From January 2005 to December 2007, he was the president and CEO of Def Jam Recordings, a tenure that was not without some complications, but also not without some notable successes (for example, kick-starting the careers of Rihanna and Ne-Yo). He became the face of the Brooklyn Nets, a publicly redeemed family man, the owner of the streaming platform Tidal, and a cognac and Champagne mogul.

As an example of his cultural influence, in the fall of 2003, he released “Change Clothes,” the first single from The Black Album, at the time his self-proclaimed final record before he retired from rapping and focused all of his attention on business ventures. In the song, he admonished the state of fashion, which at that point was dominated by the throwback jersey and massive denim, the bottoms of which would swallow the wearer’s sneakers. He insisted, instead, upon people cleaning up a bit. Wearing button-ups, tailored clothes, and—of course—his own S. Carter sneaker line, put out by Reebok, in a multimillion-dollar deal.

In retrospect, the song (regardless of how you feel about its quality) was an advertisement for a specific kind of respectability. And it worked. As someone who was at the time working in a sneaker-and–streetwear shop in my local mall in Columbus, Ohio, it was fascinating to see how immediately the style shifted, based on the demand of what people came to the mall looking for. An aspirational lifestyle was being sold, clothing as the gateway to being seen differently.

The question hovering over this hustle is: seen differently by whom? Jay-Z was emerging as the exemplar of Black Excellence, a concept I never—aside from, perhaps, Barack Obama’s first presidential campaign—found much use in. It seemed to package and sell excellence back to Black people as rarity, and not a common practice—a rarity that, whether one liked it or not, required surrendering parts of yourself. The story of what you’ve endured, for example, might become divorced from anything other than some broad strokes inspirational tale. Which was why it was so fascinating, in 2016, to receive Pusha T’s “Drug Dealers Anonymous.”

The song featured what was, at the time, a rare Jay-Z verse. A verse that trafficked in the fantasies of Reasonable Doubt, mapped onto his present life, the businessman who, at that point, was close to becoming hip-hop’s first billionaire. Rapping about his accountant finding loopholes to stash his drug money, and how his run as a drug dealer was still happening as he spoke, with a network of cars moving his stash around. I loved the verse then, and I still love it now, even though it was and is impossible to take at face value. Here was the older hustler, seeing if the tricks of tidying up his mythology still work. I found some satisfaction in that, though it was selfish satisfaction. I think, if I am being honest with myself, I was satisfied with the gap between the mythology and the reality of his life in that moment.