1. Diddy

Net Worth: $550 million
Hustles: Ownership in Bad Boy Records, Ciroc vodka, Sean John and Enyce clothing, Blue Flame marketing agency, and Revolt cable channel, with investments in various tech start-ups, along with various acting jobs, and a Beats Electronics endorsement.

Can Diddy become hip-hop's first billionaire? Sean John clothing was Diddy's first business venture outside of music. Founded in 1999, the company peaked with $450 million in sales in 2004. While Sean John is still a major player in Diddy's bottom line, Ciroc vodka has been his biggest paycheck as of late. Sales of Ciroc spiked 122% last year thanks to Diddy's relentless promotion. Forbes estimates that he'll be entitled to a nine-figure cut of cash if Ciroc is ever sold.