8. Jay Z Sells Rocawear to Iconix Brand Group (2007; $204 Million)
It still stands as one of the largest, if not the largest, hip hop clothing buyout in history. The story behind it is also epic: in 2005, Dame Dash sold his share of Rocawear to Jay Z for roughly $30 million. Not bad, considering the two had both sold Roc-a-fella together. However, when you consider that only a few years later, Jay goes out and sells the company for over six times the amount he bought it for, you have to wonder if he had been eyeing this move for quite some time.