1. Dr. Dre
Dr. Dre's 20s looked like this: was a founding member of N.W.A., the originators of gangsta rap; put out an era-defining album with The Chronic; formed the seminal rap label Death Row; helped shape the career of the legendary Snoop Dogg.
Just as his 30s were beginning, Dr decided to take a humungous leap and give that all up. He severed all ties to his past and started his own label, Aftermath Entertainment, where his first release—a compilation album titled Dr. Dre Presents the Aftermath—was anchored by the single, "Been There, Done That." The cover art was firebomb's smoke. It was a kiss-off to the type of rap he made famous; unfortunately, neither critics nor fans were ready for this new Dre.
In what amounts to nothing short of a miracle, Dr. Dre soon ended up with a demo of a young, white rapper from Detroit who called himself Eminem. Em provided Dre with a new avenue to explore music, and the results were even more historic than the N.W.A.-Death Row days. Dre has gone on to oversee Eminem's success, 50 Cent's career, The Game's debut, Kendrick Lamar's emergence, and at one point, the rebirth of his own solo career with modern classic, 2001.
And interestingly enough, his career has perhaps been eclipsed lately by the omnipresence of the headphones that bear his name, Beats By Dre.