Madonna

Britney, Christina and Jessica were all still in diapers when this unstoppable bottled blonde shot to stardom in the early '80s with her catchy pop songs and sexy, eye-catching videos. Although far from a powerhouse vocalist, the provocative diva ruled the charts for decades by repeatedly reinventing herself, both aesthetically and musically, and by constantly causing controversy, from her make-out session with a saint in "Like a Prayer" to her X-rated 1992 picture book Sex to her lip lock with Britney Spears at the 2003 MTV Video Music Awards, which was viewed by many as Madonna's unique way of passing the torch to the next generation of pop stars. Her forays onto the big screen weren't as successful. She fared best when basically playing herself (Desperately Seeking Susan, Dick Tracy, the documentary Truth or Dare), but save for Evita, which earned her a Golden Globe, her attempts to be taken seriously as an actress (the wannabe screwball comedy Shanghai Surprise opposite first husband Sean Penn, the unwatchable remake of Swept Away directed by her second husband, Guy Ritchie) were met with critical and commercial scorn, as well as Razzie Awards. While Madonna hasn't exactly mellowed with age, she has shifted her focus. After years of a love-hate relationship with Catholicism, she became a very vocal follower of kabbalah. She also became a mother of two and an author of children's books, all while sporting a body most 20-year-olds would die for.