Dr. Dre

Dr. Dre’s had more careers in one lifetime than many people can dream of.  He’s been a main force behind some of the biggest hip-hop acts in the past 15 years like Eminem, 50 Cent and Kendrick Lamar and somehow still has people waiting for Detox. Dre doesn’t really spend too much time in the spotlight, so Oprah would have years worth of stories to pull from.