Jay-Z’s initial rise in the late ’90s coincided with two significant developments within hip-hop: the high-profile deaths of 2Pac and the Notorious B.I.G., as well as the rise of Mafioso and “shiny-suited” flossy rap taking over the mainstream. Both of these played a major part in Jay’s appeal at the time. On the heels of Pac and Biggie’s deaths—as well as a romanticized fatalism pervasive in mid-’90s hip-hop—Jay’s songs and albums, while often darker than their reputation, didn’t have the same fetish for martyrdom that seemed so pervasive during the height of Murder Was the Case and “Tha Crossroads.” Jay’s musical ethos was less doomed; he wasn’t preoccupied with dying at 25, but was focused clearly on winning. Emerging at a time when Puff Daddy, Bad Boy Records and Jermaine Dupri were extolling the virtues of expensive champagne, private jets and V.I.P. lifestyles, Jay was the perfect Pied Piper of conspicuous consumption presented as upward mobility.
What separated Jay from the Puff Daddys and Dupris was an artistic credibility that gave his flossy ambitions context outside of the shiny-suit era during which he’d emerged. As that trend died, and after Jay proved he wasn’t exactly suited to pandering to it, he found his firmest career footing balancing his street-hustler history with a ballerific rap rebel: unapologetically capitalist, with the commercial savvy to match his street appeal. For a generation of rap fans, Jay came to embody the hustler spirit and hip-hop’s wildest ambitions.
Revisiting the more materialistic moments in hip-hop of yesteryear feels almost quaint in hindsight; boasts about cruising in Mustangs and Land Cruisers would eventually give way to gaudier verses about Bentleys and Maybachs. For so many, that shift epitomized hip-hop’s graduation to the “big time”: no longer satisfied with mere “hood” riches, to be a baller now meant echoing mantras of the 1 percent for the sake of showing the streets how high they could climb. And no rapper was a louder mouthpiece for the righteousness of riches than Shawn Corey Carter.
Of course, Jay-Z wasn’t the only rapper rhyming about money. But he had the most cultural sway and seemed to live it in a way that outshone virtually all of his peers. His raps-to-riches story was perfect: rejected as an aspiring artist, he’d launched Roc-A-Fella Records with partners Dame Dash and Kareem “Biggs” Burke, and through his own talent, turned “The Roc” into one of hip-hop’s most powerful labels by the early 2000s. He was living the reality so many rappers seemed to fantasize about, and as this brand of “luxury rap” became omnipresent, it changed the way rappers, critics and fans measured success—and the way the media commentated on that success. Sales and chart positions became constant fodder for music websites and entertainment blogs, and became key points of discussion when appraising a major hip-hop artist’s career and impact. Rankings on hip-hop Forbes lists and rappers’ net worths became constant talking points.
Over time, Jay’s image as a mogul came to be a touchstone for how a generation saw black wealth and success. In the second act of his career, he became one-half of the most powerful couple in music alongside his superstar wife, Beyoncé. The Carters have branded themselves the faces of black moguldom for that same generation that came of age with Jay’s mantras of “I’m a business, man” and “I can’t help the poor if I’m one of them.” In the 2010s, that branding shifted from just lucrative endorsements and high-profile tours to include a spirit of quasi-activism, taking on high-profile causes like Kalief Browder and echoing the mantras of the Black Lives Matter movement. Jay had always treated his business moves as affirmation of what a black man can and must do to garner ownership in an entertainment industry controlled by those who don’t look like him, but it also begs the question: Does black ownership within any capitalist system truly liberate black people?
That question could be an undercurrent of every facet of Jay-Z’s life and career. His early days dealing crack in the Marcy Projects are a sad commentary on what a black youth had to do to survive the Reagan era in a devastated New York City, but you can’t look past the truth of earning money from the brokenness in one’s own community. Jay’s journey forces us to stare at some of the uncomfortable contradictions present in so much of the hip-hop generation’s ambitions. We celebrate the hustler and often never get around to who said hustler exploited to rise above his circumstances. When Brooklynites complained about Jay-Z and the Brooklyn Nets building the luxury Barclays Center in a working-class area of Park Slope, it was another example of how one man’s ambitions can undercut a community’s well-being.
Those contradictions have been front and center this year. With quarterback Colin Kaepernick all but blackballed, it was a shock to many observers when Jay’s Roc Nation inked a deal with Roger Goodell and the NFL to help “advise on selecting artists for major NFL performances like the Super Bowl.” After several years of positioning himself as hip-hop’s “woke” billionaire philanthropist, Jay partnering with a league that conspired to shut out Kaepernick reeked of hypocrisy and opportunism. Kaep landing a November workout with NFL teams was viewed as empty appeasement, and Jay’s reputation took another hit when “unnamed sources” claimed he was reportedly frustrated with Kaepernick using the workout as “a publicity stunt.” A later report denied any claims that Jay was angry, but it’s clear that the public is growing ever more cynical about what Jay represents and his intentions. At this point, such cynicism is absolutely necessary—and par for the course.
When Jay announced “The City Is Mine” in 1997, so many listeners smirked and scolded his arrogance in the wake of Biggie’s death. When he broke from Dame Dash to launch Roc Nation, so much of the commentary centered on his betrayal of his former friend. And when he responded to criticism from Harry Belafonte by declaring “my presence is charity” and dissing the famed entertainer/activist, some were forever turned off by the hubris of this rich rapper who’d decided to wag his finger at a man who’d fought oppression for decades. Jay-Z’s legacy is complicated; he’s the embodiment of all a rapper can be from a commercial, cultural and even creative standpoint. But we can’t celebrate that without also acknowledging how much he’s shaped the commodification of the culture that made him.
At 50, Jay’s career is still remarkable. His evolution has been a story for the ages. There is no easy epitaph for him anymore. Jay has shaped a generation. Whether it’s for better or worse remains to be seen.
