Ashlee and Jessica Simpson
Jessica Simpson started her entertainment career as a pop singer, but gained notoriety when she starred with her then-husband Nick Lachey in the MTV reality series "Newlyweds: Nick and Jessica." Using reality television as a career jumping-off point is a recurring theme on this list. Jessica managed to immortalize tuna -- and chicken -- in her now infamous remarks about the Chicken of the Sea tuna brand by asking, "Is it chicken or is it tuna?" That and her performance as Daisy Duke in the film "The Dukes of Hazard" established her as the ditzy blond with the sweet smile and lovely voice.
Her little sister Ashlee also opted to go the reality television route to promote her singing career. "The Ashlee Simpson Show" chronicled the career and personal challenges of recording and promoting her debut album "Autobiography."