Jessica Simpson has had quite the Hollywood career. The 37-year-old first stole our hearts with her bubblegum pop music and perky personality in 1999 and only furthered our obsession with her sickeningly sweet romance with — and eventual marriage to — 98 Degrees boy bander Nick Lachey. Seriously, who can forget their reality series, Newlyweds: Nick and Jessica, on MTV? Following the early 2000s, Jessica has put her singing career (and relationship with Nick) behind her and is a proud mother of two beautiful children, Maxwell and Ace, with husband Eric Johnson. If you're looking to feel nostalgic, see her incredible transformation ahead.