Transformation

Whether wearing pigtails or glamorous long extensions, Britney Spears has been in the spotlight since her teenaged debut as the singer of "…Baby One More Time." Along with her ultra-catchy songs and tabloid-friendly personal life, her heart-shaped face and huge chocolate eyes have helped the mother of two to reach icon status. "Britney has beautiful eyes, so I focus on accentuating them," makeup artist Elan Bongiorno has said. In addition to false eyelashes, Spears uses highlighters to draw attention to her baby browns. This year, Britney is back with a world tour in support of her latest album, Circus.

1998: The one-time brunette 16-year-old scored a major hit with "…Baby One More Time."