Jessica Simpson

Jessica Simpson's break came with the release of her debut album Sweet Kisses in 1999. With her catchy singles "I Wanna Love You Forever" and "I Think I'm In Love With You," the CD sold close to two million copies. In the years since, Simpson has released three additional albums. The singer hit the small screen in 2003, starring alongside her then-husband Nick Lachey for two seasons in the MTV reality series Newlyweds: Nick & Jessica. The show turned them into one of America's most recognizable (and scrutinized) couples. The two separated in November 2005 and their divorce was finalized in July 2006. Simpson made the jump to the big screen as Daisy Duke in 2005's Dukes of Hazzard. Since her divorce from Lachey, Simpson's love life has been a hot topic of conversation. In August 2006, Simpson revealed that she had been seeing musician John Mayer. The couple's on/off relationship of eight months officially cooled in June 2007. In early 2008, Simpson supported current beau, Dallas Cowboys quarterback Tony Romo at many of his football games.