2. Snoop Dogg
Many people would like to be in Snoop Doggy Dogg’s shoes now and for a very good reason, I might add! However, when Snoop was young, I bet not even Snoop himself wanted to be in his shoes. Drugs, gangs, jail time, you name it - Snoop was indeed living that hard life, which cannot be said for many artists these days. His luck changed once Dr. Dre got his hands on one of Snoops demos and the rest… well, you know the rest. Snoop is a legend these days with enough money in the bank to support all the extravaganza he could ever wish for and, if you think he has to do music to maintain a steady cash flow, you’re sadly mistaken, as Snoop knows better than putting all his eggs in one basket. He has his own record label, merchandise, fashion, even his own drink and action figures!