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?

David Dennis, Jr.
LEVEL
Published in
12 min readAug 31, 2020

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

Update 6/7/22: Level has a new home. You can read this article and other new articles by visiting LEVELMAN.com.

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…

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David Dennis, Jr.
David Dennis, Jr.

Written by David Dennis, Jr.

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