Back in 1999, Sean Combs–known as Puff Daddy at the time–appeared on the cover of the first-ever Celebrity 100 issue. Instead of sporting a snappy suit (as this year’s cover star The Weeknd did), Combs donned a t-shirt bearing the logo of his new clothing line, Sean John, for the cover shoot.
Nearly two decades later, that sort of in-your-face marketing has paid off: Combs, now better known as Diddy, tops this year’s Celebrity 100 list with pretax earnings of $130 million, a career best. Today he sits atop an empire that includes a lucrative partnership with Diageo’s Ciroc vodka and hefty stakes in companies including Revolt TV, DeLeón tequila and Aquahydrate alkaline water.
But the bulk of Diddy’s 12-month haul came from the estimated $70 million he pocketed when Global Brands Group bought a majority stake in Sean John last November. The deal left him with a reported 20% of the company he founded and grew into an international brand that now does nearly half a billion dollars in annual sales.
“When we started Sean John, it was my dream to build it into an aspirational brand for the young consumer,” said Diddy at the time of the deal. “Our new partnership … provides us the opportunity to reach the Millennial customer on a global level.”
Diddy’s Sean John windfall pushed him past listmates including Beyonce (No. 2, $105 million) and Drake (No. 4, $92 million) to claim the top spot on our earnings list. He earned more than Ed Sheeran (No. 71, $37 million), Britney Spears (No. 89, $34 million) and Chance the Rapper (No. 95, $33 million)–combined.