Chappelle 's Show was an American comedy television series starring comedian Dave Chappelle . The third season of Chappelle 's Show was scheduled to premiere in February 2005 . This date was pushed back to May 31 , 2005 when production fell behind schedule in December 2004 because , according to Comedy Central , Chappelle had fallen ill with the flu ( Chappelle later told Oprah Winfrey that this was untrue and that stress had caused him to leave ) .