Net worth: $820 million

Diddy embodies what it means to be a rapper with money. His first album, No Way Out, was certified seven times platinum. His clothing company, Sean John, has an annual revenue of 525 million dollars. His deal with Ciroc nets him half of their profits. Diddy is also the head of Combs Enterprises, an umbrella company that includes Bad Boy Entertainment, and various other successful companies and brands. With his net worth nearing in on a billion dollars, Diddy has proven himself to be not just the most successful businessman in hip-hop, but also one of the most successful businessmen, period.