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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.

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