Today, Jessica Simpson is a business mogul. In 2016, she sold a majority stake in her booming lifestyle brand, the Jessica Simpson Collection, which Forbes reported was then bringing in $1 billion annually, helping the star amass a net worth of $170 million.

Before that, she was a pop star with a slew of other successes: Her 2006 album "A Public Affair" sold over 100,000 copies in its first week, according to Rolling Stone, and singles like "These Boots are Made for Walkin'" and "Come Over" were hits. She's appeared in TV shows like MTV's Newlyweds (2003) and movies including "The Dukes of Hazzard" (2005) and "Employee of the Month" (2006).