===2008–09: Move to country music and "Do You Know"===In September 2007, Simpson's father, and manager, Joe Simpson stated to "People" magazine that Simpson was considering doing a country album.
V decembru 2006 je Jessica Simpson z Dolly Parton nastopala na podelitvi nagrad Kennedy Center Awards, kjer je njen nastop dobil nizek uspeh pred množico, med občinstvom pa so bile tudi pomembne osebe, kot naprimer Steven Spielberg, Shania Twain in predsednik George W. Bush.