In June 2005 , Chappelle performed impromptu stand-up shows in Los Angeles , then went on a tour that began in Newport , Kentucky , not far from his Ohio home . He made a surprise appearance on HBO 's '' Def Poetry '' , where he performed two poems , titled " Fuck Ashton Kutcher " and " How I Got the Lead on '' Jeopardy! '' " In an interview with Oprah Winfrey that aired on February 3 , 2006 , Chappelle explained his reasons for quitting '' Chappelle 's Show '' . He also expressed his contempt for the entertainment industry 's tone-deafness regarding black entertainers and audiences : Chappelle was interviewed for '' Inside the Actors Studio '' on December 18 , 2005 , at Pace University 's Michael Schimmel Center for the Arts . The show premiered on February 12 , 2006 . Four days earlier , he had introduced the musical tribute to Sly Stone at the 48th Annual Grammy Awards
48th Annual Grammy Awards
48th Annual Grammy Awards
Dave Chappelle