The Forbes Five: Hip-Hop’s Wealthiest Artists 2014

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Diddy leads the pack with an estimated fortune of $700 million, an increase of $120 million over his net worth last year. The change comes largely from the addition of Revolt TV—the new, music-focused, multi-platform channel of which he’s the majority owner—to his already-hefty portfolio.

“Right now my focus is Revolt and making it the number one, most-trusted, most credible worldwide brand for music,” he told FORBES in a recent interview. “And  to get Revolt to be the quintessential definition of real time. I think that’s the future.”

Diddy has plenty of competition in the race to $1 billion. His top challengers are Dr. Dre, who ranks second with $550 million, and Jay Z, in third place with an estimated $520 million. The former leapfrogged the latter on this year’s Forbes Five thanks to a large stake in Beats By Dr. Dre, which he cofounded with Interscope chief Jimmy Iovine in 2008.

The company controls an astounding two-thirds of the premium headphone market, with annual sales reportedly in excess of $1 billion and growing. Private equity firm Carlyle invested $500 million for a minority stake last year, pushing Beats’ value past $1 billion and likely closer to $2 billion.

“Beats has a unique brand—it speaks to a nice young demographic, which is really interesting to marketers,” says Peter Csathy, former president of Musicmatch, an early digital music purveyor acquired by Yahoo YHOO +6.26% in 2004 for $160 million. “When I think about Beats, I think about it as a lifestyle, I think of it as a media company, not just a hardware and music-focused company.”

Full coverage: Hip-Hop’s Wealthiest Artists 2014

Jay Z’s fortune continues to grow at a healthy clip, too. He’s made multiple nine-figure deals in the past, including his $204 million Rocawear sale in 2007 and his $150 million pact with Live Nation in 2008. But much of his recent growth comes from Roc Nation, his record label and management firm that recently added a sports agency. The outfit gets a single-digit cut of pacts like Robinson Cano’s $240 million monster agreement.

(For more on Mr. Carter’s rise as a businessman, check out Empire State of Mind: How Jay-Z Went From Street Corner To Corner Office).

Next  up: Bryan “Birdman” Williams, whose net worth would be over $300 million if he didn’t share his fortune with brother Ronald “Slim” Williams. The duo cofounded Cash Money Records two decades ago; Cash Money continues to grow with a roster that includes Drake, Nicki Minaj and Lil Wayne. Birdman has also diversified with Cash Money Content, GT Vodka and the YMCMB clothing line.

Rounding out the list is 50 Cent, who owes most of his fortune to his $100 million haul from the sale of Vitaminwater in 2007. Now he’s trying to repeat the feat with companies like SMS  Audio and SK Energy beverages. In the meantime, he’ll reboot his music career by taking his G-Unit Records independent and releasing new album Animal Ambition in June.

“It was getting pretty difficult to launch music that everyone was paying attention to at the same time,”  says 50 Cent of his final days at Interscope, the label that launched him to superstardom. “The company itself was going through so many changes that I didn’t really know the people involved in the projects anymore.”

In order to complete our Forbes Five list, we follow the same procedures we follow while calculating our list of the world’s billionaires: looking at past earnings, valuing current holdings, leafing through financial documents and talking to analysts, attorneys, managers, other industry players and even some of the moguls themselves—like Diddy, who already has his eye on the next generation.

“My advice to future entrepreneurs is to always know reality, to know what you’re getting yourself into, to know how hard it’s going to be, how competitive it’s going to be,” he says. “We’re in a time where the people that really work hard—and really believe in themselves, and really don’t give up on their dreams, no matter how many times they fall down—are the ones that are going to be successful.”

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