P. Diddy

With an estimated wealth of $346 million, album sales of over 12 million, and business ventures in everything from clothing lines to vodka and restaurant chains, Sean "Puffy" Combs became the ultimate bling-encrusted hip hop entrepreneur. Raised in New York City, Combs dropped out of college to become an executive at Uptown Records, signing Mary J. Blige and helping to produce Jodeci before establishing his own label Bad Boy Records in 1993. Gradually becoming the solo star Puff Daddy, he scored a US Number 1 with his debut single Can't Nobody Hold Me Down, but was overshadowed by the vicious East Coast vs West Coast feud with Suge Knight's Death Row Records; which culminated in the murder of his friend Notorious B.I.G. and rival rapper Tupac Shakur. Combs reworked the Police song Every Breath You Take into the tribute single I'll Be Missing You and it proved a huge success, topping the charts around the world and spending 11 weeks as US Number 1. Through name changes, high profile relationships and run-ins with the law, P. Diddy (as we think he's calling himself this week) stands as a hard-partying, hip hop tribute to the American Dream.