Born: July 10, 1980
Jessica Simpson began her career as a bubble gum pop star, but quickly went on to make a name for herself in Hollywood. From releasing albums and starring in the remake of The Dukes of Hazzard to launching a successful fashion empire, Jessica has her hands full.
Born: October 3, 1984
In the span of a few years, Ashlee Simpson-Wentz went from cutesy pop star to punk rocker and even suffered public humiliation in 2004 when she was caught lip syncing on SNL. She took an extended career break in 2008 to get married and have a baby with Fall Out Boy's Pete Wentz.