Jessica Simpson & Rosie O'Donnell

Although Jessica Simpson dabbled in film, reality TV, and eventually contemporary country music during the 2000s, she is best known as a dance-pop vocalist who rose to fame in the late '90s alongside such teenaged acts as 98°. Simpson was born and raised in Dallas, TX, where she began her performing career as a member of her church choir; at 12, she also auditioned unsuccessfully for The Mickey Mouse Club. While attending church camp the following summer, Simpson was discovered by the head of a tiny contemporary Christian music label and spent the next three years recording he...