Hip-Hop at a Crossroads

The Billionaire’s Lament: How the World Changed Around Jay-Z

His three-comma aspirations inspired millions. But what now, when billionaires are under fire?

Photo illustration: Moya Garrison-Msingwana; Image source: Shareif Ziyadat/Getty Images

As the summer of 2020 draws to close, it’s clear the world has changed in unprecedented ways. A pandemic, its ensuing economic fallout, and a broad-based racial justice movement—not to mention the toxic, repressive administration that serves as their backdrop—have disrupted our lives in ways we scarcely could have imagined. If ever there was a moment for hip-hop to realize its promise as a political and cultural corrective, it’s this one. Throughout the week, LEVEL will be publishing stories that examine the summer of 2020 through the lens of hip-hop — from its relationship to the world at large to its own structural issues.

Jay-Z and Pharrell’s recent song “Entrepreneur” once would have seemed impossible. Not because it was released in conjunction with a Pharrell-curated issue of TIME magazine or because it tackled ideas of financial independence and generational wealth but because the idea of a Jay-Z verse was met with a collective groan before the song even came out. Something that used to be so highly anticipated has become fodder for arguments over paths to freedom and signs that the greatest rapper alive is out of touch with the current movement. Shawn Carter’s prosperity gospel, the same thing we used to lift him up for espousing, has now become his greatest detriment.

How did we get here? And what can Jay-Z do about it?

Rap is an artwork based on aspiration. Rappers making music about the nature of what it means to live as Black people in America couched those revelations in the hopes of what it means to transcend those circumstances. If rap is the hood CNN, as Chuck D has always proclaimed, it’s also been the hood HGTV where we can hope for the million-dollar houses of our dreams. In fact, the “first” rap song — or at least the first one fed to the rest of America — “Rapper’s Delight” has Big Bank Hank rapping about a Lincoln Continental and a sunroof Cadillac.

This isn’t anything new for Black culture; many would-be liberators have seen our path to freedom paved with platforms based on economic advancement. From Tulsa’s “Black Wall Street” to Marcus Garvey’s economic principles to Martin Luther King’s ideas of Black employment, the ideals of Black liberation have long gone hand-in-hand with economic gain.

As rap became a more commercial art form in the ’90s, it became a path for getting out of the hood and even one for establishing Black business bases across the country. Rappers spent much of the early ’90s in a tug of war between the idea of selling out for millions and “keeping it real,” eschewing the riches for a more authentic product; whatever that ultimately meant was always up for interpretation.

That battle ended when the word “millions” started entering the equation. Even the most anti-establishment of artists cashed out. Hell, half of the group that screamed “Fuck the Police” went the route of movies and commercials. By the mid-’90s, mainstream hip-hop’s supreme focus became about who had the clearest path to the most money.

That’s where Jay-Z comes in. The Brooklyn MC made no qualms about his desire to be rap’s money king from the beginning, rapping about yachts and Lexuses on his debut album, 1996’s Reasonable Doubt. By 2001, he was rapping about numbers that rap hadn’t seemed capable of even conceptualizing, verbalizing desires to be a “hundred million man.” But a funny thing happened with all of that dreaming: Jay-Z actually achieved his goals.

A large part of the Jay-Z brand and the Hov experience was watching him go from unsuspecting MC to one-man corporate behemoth. What made Jay even more special was that, unlike Dr. Dre or Diddy — who may occupy higher spots on Forbes lists on a given year partly due to their production credits — Jay made it first and foremost as a rapper. “I came to take this shit and I did,” he spit on “Heart of the City (Ain’t No Love)” in 2001. “I handle my biz.”

Jay’s climb through the socioeconomic ladder was a testimony that any street hustler who has to survive in America is just as intelligent as any White corporate executive.

Every subsequent business venture was foretold through rap, a reflection of the acumen he demonstrated when he lost 92 bricks and regained them. Jay’s climb through the socioeconomic ladder was a testimony that any street hustler who has to survive in America is just as intelligent as any White corporate executive. He was an avatar for Black men’s potential. The “what if” for every cousin we lost to the streets. The reminder that the thing holding our dads and brothers back isn’t their own shortcomings but an oppressive system. He made us want to be Jay-Z while also making us feel like we were Jay-Z.

Just look at the previously restricted doors Jay kicked down. He went from rapping about Hilfiger to having his own clothing line at Sears. He went from rapping about clubs White people owned to opening the 40/40 Club. He went from rapping about Cristal to dismissing them when they shunned rap, eventually co-owning Ace of Spades and D’Ussé. He went from rocking throwback jerseys to being a minority owner of the Brooklyn Nets. When he grew tired of the payouts from streaming services, he launched Tidal. All on the way to becoming rap’s billionaire. He achieved every capitalistic dream any rapper could hope to accomplish. And he was revered for it.

It’s important to note here that while Jay-Z has been credited with setting blueprints, he seemed to be following the example set by the Black male celebrity who dominated the generation before him: Michael Jordan. There’s always been a belief that Jordan’s impact stemmed in part from the subversiveness of his being Black in rooms where Black people had previously not been welcome. As with Jordan, that belief helped Jay coast through much of his career unchallenged. And if there were dissenters, Hov fans were quick to pounce — even taking his side over Harry Belafonte when the civil rights icon criticized Jay in 2013. (“I think one of the great abuses of this modern time is that we should have had such high-profile artists, powerful celebrities,” Belafonte told the Hollywood Reporter. “But they have turned their back on social responsibility. That goes for Jay-Z and Beyoncé.”)

Jay’s response? To proclaim during an interview with Elliott Wilson that “my presence is charity.” He saw his ability to be in White spaces as a rising tide that would lift all ships. Some thought that was all Jay needed to do. Others still wanted more.

When police officer Darren Wilson gunned down Mike Brown in Ferguson in 2014, almost a year to the day after Belafonte made his remarks, the spotlight shone on celebrities and what they were going to do to buttress the modern-day civil rights movement like never before. The hypothetical became real: What are Black celebrities going to do for their people?

Jay-Z and Beyoncé were two of the celebrities tasked with answering the call. The couple would provide legal fees for arrested protesters. They’d pay for funeral services for those killed by police. They’d show up to protests for the likes of Eric Garner as secretively as possible. They set up private jets for Ahmaud Arbery’s attorney. Jay penned an op-ed about criminal justice reform for the New York Times. He produced a documentary on Kalief Browder.

Was it enough? That’s always up to personal interpretation of what one sees as worthy contributions to liberation. Some will always ask for more and be well within their rights, just as those satisfied by his acts have their own metrics that may or may not be influenced by fandom. Whatever the case, it seemed as though, at the very least, Jay was increasing his effort to change with the times and move toward becoming the transformative Black leader people were looking for.

Then Jay-Z sat at a table with NFL commissioner Roger Goodell, and everything went to hell.

“We’re past kneeling.”

Last August, Jay-Z and Goodell announced a partnership that would allow Roc Nation to “advise on the selection of artists for major NFL performances like the Super Bowl. A major component of the partnership will be to nurture and strengthen community through football and music, including through the NFL’s Inspire Change initiative.” Maybe Jay-Z saw himself changing the NFL from within. Maybe he saw some overall benefit to social justice that we can’t see. It’s possible Jay saw this as a move that got him closer to owning a football team, the charity of his presence gaining him entry to another room routinely denied Black people. Maybe he saw his seat at the table, once again, as something that could benefit more than himself. Whatever the case, the partnership — and the optics of Jay laughing it up with Goodell while Colin Kaepernick was blackballed from the league — was a public-relations disaster for Jay.

Therein lies the conundrum of 50-year-old Jay-Z and the current state of the world. His whole legend is based on capitalist aspirations — and just as he’s realizing his billionaire dreams, the rest of the world is seeing the nefariousness at the heart of those dreams.

Despite the negative reactions (including from Kaepernick himself), it was another shrewd business move in the fact that it will line Jay’s pockets once again. And therein lies the conundrum of 50-year-old Jay-Z and the current state of the world. His whole legend is based on capitalist aspirations — and just as he’s realizing his billionaire dreams, the rest of the world is seeing the nefariousness at the heart of those dreams.

Critics of the idea of economic liberation are quick to mention that capitalism as a construct, especially in America, will inevitably lead to the oppression of the most vulnerable people. Capitalism is rooted in oppression, and desiring to succeed at capitalism has an inherent consequence of leaving marginalized groups behind. Those voices have always existed, even back to the civil rights movement. Now, those voices are louder and more mainstream than ever before.

Trumpism has shown how deadly it is to have a country that worships the rich. The mainstreaming of politicians like Bernie Sanders and Elizabeth Warren with their policies of wealth taxes has shown just how much billionaires could contribute to society if they were docked at the rate of the middle class. A pandemic has peeled back the veneer of American opportunity: Most of us are left without safety nets while billionaires get richer. We are all scraping by and watching celebrities go unscathed while refusing to relinquish their wealth in any meaningful way. In short, billionaires are the bad guys.

In the middle of this seismic shift is Jay-Z, who made no secret about his desire to be a nine-figure hero and was praised with every step he made toward that landmark. Now he looks around and sees a world where what we loved about him has become what so many championing liberation despise. Jay has been the same since 1996; it’s the world that’s changed.

At times, Jay seems lost in all of it. He has focused much of his music on trying to teach listeners how to use capitalism to the benefit of the general Black populace. The tropes are all there: generational wealth, investment in our own communities, owning our own businesses. “Take your drug money and buy the neighborhood, That’s how you rinse it,” he rapped on “The Story of OJ.” The song is from his 13th album, 4:44 which, tellingly, is one of his strongest projects to date largely because most of its focus is on his reckoning with his marriage while keeping much of the scope extremely insular. It’s when he preaches capitalistic gain is the way to get free that he invites the most scathing criticisms.

His music, once full of lines like “I’m not a businessman / I’m a business, man” that we repeated ad nauseam, has been replaced with mantras about entrepreneurship that sound more like “pull yourself up by your bootstraps” than revolutionary. When he rapped a tribute to Nipsey Hussle, he opened with “gentrify your own hood before these people do it.” The verse wrestles with the nature of “home” in light of the fact that Nip was killed in his own neighborhood he was trying to improve — but the idea of trying to turn “gentrification” into something positive when the very nature of gentrification is rooted in disenfranchising Black folks just didn’t fly. Especially when receipts show how Jay’s partnership with the Brooklyn Nets damaged Black neighborhoods and brought about its own form of gentrification.

Which brings us to “Entrepreneur.” The eye rolls were immediate by the time the song name-dropped and the line “Black Twitter, what’s that? When Jack gets paid, do you?

For every one Gucci, support two FUBUs” started circulating. The song followed suit with more bars about wealth getting us free. Again, contradictions abound. While the rest of us were wearing Black-owned urban gear like FUBU and Jay’s very own Rocawear, he was touting Maison Margiela and making songs named after Tom Ford. Two lines later, he’s touting the aforementioned D’Ussé and Ace of Spades which, despite his part-ownership, are still White-owned brands.

Black businesses are objectively a good thing. I don’t think anybody would argue any differently. However, I’m not sure how innovative a concept that is at this point when there are so many Black people actively trying to be our own bosses. Who exactly is Jay preaching to about the importance of Black ownership especially when we know that a pandemic and government-sanctioned racism has wiped out more than 40% of all Black small businesses in the country? When these businesses and LLCs fall apart, then what? What does freedom for Black folks look like to someone who claims that he’s a one-of-one? And what about us who want to get free without that freedom being tied to economic worth? What about those of us who just want to exist in a world where we are treated equally without that being tied to how much money we earn? We know police bullets don’t care if the Black skin they pierce belongs to business owners or the unemployed. Hospitals aren’t concerned with our credit scores when they see Black women in labor and refuse proper treatment. Where is Black liberation outside of the reaches of capitalism? What’s free?

The capitalistic Jay-Z backlash has reached the point where he’s become the source of multiple internet memes making fun of the same businessman preachings. “Roc Nation Brunch Twitter” has evolved into a pejorative for men who preach about 401(k) funds and shame people for not using their stimulus checks to form LLCs. The same for “chess not checkers Twitter” and the recurring question: “Would you rather $50,000 or dinner with Jay-Z.” This, of course, is out of Jay’s control — but it’s birthed out of an interpretation of the music he’s been making.

It’s at this point we have to address the elephant in the room: The only other artist in the world with Jay’s stature and fame has been the one setting the blueprint for transformational works of art that feel like freedom. And that artist just so happens to be his own wife. While Jay is asking why we don’t buy FUBU, Beyoncé is dedicating her entire website to highlighting Black-owned businesses. When Jay is talking generational wealth, Beyoncé is speaking on restorative emotional healing across generations. From Lemonade to Black Is King, Beyoncé is doing so much of the work the world sees Jay as lacking. Of course, her own wealth prevents her from being above reproach, but she certainly is able to put out music without the same vitriol her husband receives. Jay’s approach only feels more neutered by comparison.

Sometimes I think Jay is trying his best, and his means of getting us free are just misguided. Other times my cynicism leads me to believe he’s all about the bottom line for himself without caring much about the rest of us. The truth is probably somewhere in the middle: He believes his capitalistic gain makes all of our lives better, no matter how futile that endeavor appears. Maybe it’s my own fandom that makes me believe that Jay-Z’s heart is ultimately in the right place and he’s just not capable of wrapping his head around what’s being asked of him.

I’m not one to give too much sympathy to a billionaire. They’ll be fine in the long run — and ultimately better off than I’ll ever be. But there are times when I feel badly for Jay-Z. He used to determine cultural shifts on a whim. Now the culture keeps shifting faster than he seems able to make sense out of. Not only that, but the culture has moved in the exact opposite direction from when it propelled him to the nigh-deity he is now. To paraphrase Jay, the world is good night-ing him with the same sword it knighted him with. Those lyrics, by the way, are from 15 years ago — back when the future was as clear as it was stable.

Level Sr. Writer covering Race, Culture, Politics, TV, Music. Previously: The Undefeated, The Atlantic, Washington Post. Forthcoming book: The Movement Made Us

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