Reflecting on Hip-Hop's 50 Greatest Moguls

To celebrate hip-hop’s 50th anniversary, we ranked hip-hop’s 50 greatest moguls. Friend of the pod, Zack O’Malley Greenburg, hit me up with the idea and I was down. We reached out to several experts, published the official list on his site, and discussed the full list breakdown on the latest Trapital episode. Here are a few key themes below from our chat.

“Mogul” is about more than making money

There’s a strong correlation between hip-hop’s wealthiest artists and its moguls, but they’re not identical. Moguls make an impact beyond personal financial gain. They create opportunities for those around them.

Jay-Z said it best in his verse on Drake’s “Pound Cake.” He shouted out his past business partners, who are now millionaires, and others in his orbit who became billionaires, like Kanye West, Rihanna, and LeBron James. If an artist is wealthy, but the people they came up with aren’t broke, that’s a knock against the artist. A mogul’s king or queen-making ability matters.

There’s also a longevity factor. Some people may be considered moguls because of one or two lucrative products or investments, but their business performance struggled in several other years. I weigh consistency and longevity above short-term dominance. It’s more likely to lead to successful results, especially in media—where companies that chase the hot trends often lose those who are in it for the long haul.

Indirect influence also plays a factor. Nipsey Hussle didn’t close nine-figure deals or put his friends into positions of power, but his business mentality lives with other artists and entrepreneurs. The marathon continues.

You can read the list here, listen to our episode here, or read below for more highlights.

Why super producers make great moguls

Several of hip-hop’s well-known producers landed relatively high in our rankings, from Dr. Dre (#2) and Kanye West (#8), to Pharrell Williams (#22) and Swizz Beatz (#27).

Sure, there’s a skew towards hip-hop’s most famous names (we’ll get to that later), but it’s more than that. Great producers must be organized, communicate effectively, think big picture, and pay precise detail.

For instance, before age 20, Swizz Beatz had already made beats for DMX, Jay-Z, and Noreaga. He had to navigate powerful personalities at an early age, which set the tone for a career of doing it. His role at Verzuz largely depends on his ability to leverage relationships and skills to close deals. His brand partnerships with Bacardi and Lotus require him to translate his insights to the boardroom. The skillsets are transferable.

The same is true for Dr. Dre and Kanye West. Dre’s inventive genius in music production directly translated into well-designed headphones. He had the perfect match with longtime business partner Jimmy Iovine. Kanye’s creativity in music came through in his fashion, leading to the Adidas Yeezy partnership’s rise (and fall).

But since these producers have all been established for over 20 years, who has next?

I got my money on Metro Boomin. Like Swizz, Metro was a teenager when he made beats for hip-hop’s biggest stars. When Metro was in high school, his mother often drove him from St. Louis to Atlanta so he could collaborate with artists. That story sounds like a future excerpt from a Malcolm Gladwell book.

In 2023, the Morehouse College dropout sold his publishing catalog to Shamrock Capital for a reported $70 million. He’s been consistent for his entire music career and is still under 30 years old.

If Metro Boomin ever starts a company and raises capital, I would be interested off of his name alone. That producer pedigree is strong.

Which moguls are overvalued and undervalued?

Our hip-hop mogul ranking, and several others I have read over the years, often rate the impact of artist-turned executives higher, and rate the impact of non-artist executives lower.

Drake (#16), Eminem (#19), and Lil Wayne (#36) all landed much higher than expected. Each artist had respective moments as the highest-selling rapper in the world, but they had less impact beyond their individual accomplishments. Wayne may have the best claim of the three with the impact of Young Money, but launching a successful imprint is different than launching a successful standalone business.

Meanwhile, the late Chris Lighty (#30), Steve Stoute (#40 tie), and Desiree Perez (#40 tie) are too low. The first season of the podcast series Mogul is all about Chris Lighty. Without Lighty, 50 Cent’s Vitaminwater deal doesn’t happen. Stoute has always been the connector between hip-hop and Corporate America. And Roc Nation’s CEO Desiree Perez rarely does interviews, which means she’s less visible than the artists-turned execs.

At the end of the episode, Zack and I broke down our dream leadership team to run our empires. The non-artist executives got a lot of love there. We also discussed our honorable mentions, how we created our lists. You can listen to the episode here or read our list here.

Many thanks to Andrew Barber, Binta Brown, 24kGoldn, Michelle McDevitt, Jinx, Shea Serrano, LaRussell, Benny Pough, Carl Chery, and others who shared their insights for this list!‍