1. Sean “Diddy” Combs ($550 million)
Diddy has remained a mainstream mainstay for 15 years thanks to his knack for self-promotion. Lately, he’s been channeling that energy toward Ciroc vodka, much to the benefit of his bank account: he receives double-digit millions annually as a share of the spirit’s profits. Better yet, he’s entitled to a nine-figure chunk of cash if Ciroc is ever sold. He also boasts stakes in clothing lines Sean John and Enyce, marketing firm Blue Flame, record label Bad Boy, a handful of tech startups and cable channel Revolt, slated for a 2013 debut—all of which means he’s well on his way to becoming hip-hop’s first billionaire.
2. Sean “Jay-Z” Carter ($460 million)
Unlike his fellow Forbes Five members, Jay-Z still churns out music and goes on tour—most recently with pal Kanye West—adding to his considerable war chest. He sold his Rocawear clothing label for $204 million in 2007 and signed 10-year $150 million deal with Live Nation in 2008, and also holds stakes in the New Jersey Nets, his 40/40 Club chain, ad firm Translation, cosmetics company Carol’s Daughter and other businesses.
3. Andre “Dr. Dre” Young ($260 million)
Fittingly, the bulk of this super-producer’s wealth comes from headphones. In August, handset maker HTC paid $300m to buy a 51% stake Beats Electronics, the company founded by Dr. Dre and Interscope chief Jimmy Iovine in 2008. Sources say each owned a third of the company before the deal, placing Dre’s cut at $85 million after taxes. The agreement also values his remaining stake at $100 million, which could increase rapidly as the company continues to expand.
4. Bryan “Birdman” Williams ($125 million)
The Cash Money Records cofounder would be higher on this list if he held sole ownership of his label, but he shares it with brother Ronald “Slim” Williams. The duo founded Cash Money two decades ago, inking very favorable $30 million distribution deal with Universal in 1998. The label’s value has soared with the success of rappers Drake, Nicki Minaj and Lil Wayne (who shares in the ownership of sub-label Young Money). There’s even more cash on the horizon—the label’s deal with Universal is up this summer, raising the prospect of a bidding war for the right to distribute Cash Money’s releases.
5. Curtis “50 Cent” Jackson ($110 million)
The Queens-born rapper earned $100 million for his Vitaminwater stake in 2007, and then spent freely on cars and renovations to his Connecticut mansion, formerly owned by Mike Tyson. But a nice cushion remains from his back catalog, acting gigs and 50 Cent-themed videogames, books and clothes, as well as new headphone line SMS. Next up: an energy shot called Street King, which promises to feed hungry children—and 50’s bank account.