Pay: $83m

While most of us pine for retirement, the native New Yorker couldn't stand the view from the sidelines following his 2003 farewell 'Black Album'. Despite a busy schedule with his comeback album, 'Kingdom Come', he also owns a small stake in the New Jersey Nets, plus two locations of his 40/40 clubhouse. In March, he sold his Rocawear apparel label to Iconix for $204 million.