6. Russell Simmons Sells His Stake in Def Jam to Universal Music Group (1999; $100 Million)
The late '90s was a swinging time for hip hop. After years of keeping Def Jam afloat and turning it into a multi-million dollar empire, Russell finally managed to set a new bar by selling the legendary company. It was one of the first times that a major label not only recognized the power of having a hip hop label, but was willing to pay nine figures in order to have it. This move put Russell in a whole new tax bracket and thus began the corporatization of hip hop music.