Jessica Simpson
Simpson dropped out of J.J. Pearce High School in Richardson, Texas after signing a contract with Columbia Records, though she later earned her GED. Her debut 1999 album, Sweet Kisses, included hits like “I Wanna Love You Forever,” which earned her a platinum certification from the Recording Industry Association of America. Now, she’s an entrepreneur who focuses on The Jessica Simpson Collection, a fashion line available at Macy’s and Dillard’s.