Date: September 2009
For years, Oprah Winfrey had a contentious relationship with hip-hop. Things came to a head in 2006 when she was rather inhospitable to her guest Ludacris when he visited her show along with the rest of the cast of the film Crash. After that, Luda and other rappers like Ice Cube and 50 Cent started calling out Oprah, saying she had an anti hip-hop bias.
That's why when Jay Z ended up on her show in 2009, it was a pretty big deal. They talked a number of topics, from how hip-hop has brought people together to Jay's use of the n-word. If having Oprah finally aknowledge a rapper wasn't enough, Jay even brought her to Marcy for part of their interview. Later on "On To The Next One" Jay boasted, "Meanwhile I had Oprah chilling in the projects/Had her out in Bed-Stuy, chillin' on the steps/Drinking quarter waters, I gotta be the best." However, 50 Cent was still unamused. On "Play This On The Radio" he rapped, "I don’t wanna sip tea or chit chat on your sofa/Bitch I ain't Jay Z, fuck you Oprah!" —Insanul Ahmed