Sean “Diddy” Combs rose to mainstream fame in the late 1990s rapping about his desire for Benjamins, otherwise known as $100 bills. A decade and a half later, he might need to consider some larger denominations—McKinleys, Clevelands and Madisons, perhaps—to express his wealth.

Diddy ranks No. 1 on this year’s Forbes Five, our list of hip-hop’s wealthiest artists, with an estimated net worth of $580 million. The bulk of the Bad Boy Records founder’s wealth comes from non-musical ventures, namely his deal with Diageo’s Ciroc. The agreement entitles him to eight-figure annual payouts and a nine-figure windfall if the brand is ever sold—and Ciroc’s value has never been higher.

“It is one of the fastest-growing brands within vodka,” says Jack Russo, an equity analyst at Edward Jones & Co. “Consumers are feeling a little bit better about their situation, and with that, they’re willing to spend more on premium products.”

The No. 2 spot goes to Shawn “Jay-Z” Carter, with a net worth of $475 million. He’s still rolling in cash from megadeals like his $204 million Rocawear sale in 2007 and his $150 million pact with Live Nation the following year. He continues to hold stakes in Roc Nation, Carol’s Daughter, the Brooklyn Nets—and, more significantly, the Barclays Center itself—while adding new partnerships with the likes of Duracell, Budweiser and Bacardi’s D’ussé Cognac.

Andre “Dr. Dre” Young ranks third with $350 million, thanks mostly to his Beats by Dr. Dre headphones. A year after selling 51% of the company to handset maker HTC for $300 million in August 2011, Dre and his partners bought back half of the half they sold in 2012—and their investment continues to soar in value due to Beats’ whopping 65% market share of the premium ($99 and up) headphone market.

Bryan “Birdman” Williams owns the No. 4 spot, riding his Cash Money/Young Money empire to a fortune of $150 million. His roster includes Drake, Nicki Minaj and Lil Wayne (the latter crossed the $100 million threshold for the first time this year, by our estimates, but remains just outside the top five). Birdman also recently launched a YMCMB clothing line and a spirit called GT Vodka.

“We have to build different brands,” he told FORBES last month. “That’s what it’s all about.”

Rounding out the list is Curtis “50 Cent” Jackson at $125 million. He’s another master of brand building: The bulk of his fortune came from heavy sales of his music, merchandise, video games and books in the wake of his smash debut Get Rich or Die Tryin’—and particularly from his payout for the sale of his stake in VitaminWater parent Glacéau to Coca-Cola in 2007.

Now he’s trying to replicate that feat with companies like SMS Audio, his answer to Dr. Dre’s Beats, and SK Energy, which has its sights set on category leader 5-Hour Energy. When informed that his net worth would be estimated at a little over $100 million this year, 50 Cent said simply, “That’s cool.” After being asked to elaborate, though, he changed his tune slightly.

“Oh, you want me to tell you an exact number?” he said with a grin. “I’ve got way more.”

If his new ventures continue to grow, 50 Cent’s number on this list should begin to reflect that belief as soon as next year.

As for Diddy, he may need to stick to Benjamins after all. According to a recent tally, there were only 165,372 $1,000 bills still in use—not even enough to cover one-third of Diddy’s fortune.