Jessica Simpson

Jessica Simpson - Debuting as an adorable, all-American-looking pop singer with a powerful vocal range and squeaky clean image, Jessica Simpson initially stood in the shadows of her equally young, equally blonde pop predecessors Britney Spears and Christina Aguilera in her early career. Routinely compared to the two divas—sometimes unfairly—Simpson has struggled to be nothing more than herself.  Read Jessica Simpson’s full biography.

Jessica Simpson was discovered by the head of a tiny CCM label and spent the next three years recording her debut album. The label, however, folded before the record could be released, although a small pressing was eventually funded by her grandmother.

Nevertheless, the teen became a hit on the Christian Youth Conference circuit, also sharing bills with Kirk Franklin, God’s Property, and CeCe Winans. Seeking to expand her popularity in the secular market, Simpson later signed to Sony and toured in support of boy band 98°. Her 1999 major-label debut, Sweet Kisses, launched her career.