4. 50 Cent
50 Cent may have grown up in one of the roughest neighborhoods in America, but he most certainly has come a long way to where he now lives. The rapper owns several homes across the country, with his biggest one being in Connecticut — of course, we know this since 50 never fails to post photos of his multi-million dollar mansion on Twitter. The platinum-selling artist, who now releases music independently, famously said that one of the reasons he gambles so much money on boxing matches is because he will always make more of it. Cocky, arrogance or confidence? You decide.