8. Britney Spears
We've got this picture up at the office to remind us it only gets better. Spears started off as an innocent Mouseketeer of The Mickey Mouse Club and was already flirting with naughtiness in the video for her first single, "Baby One More Time." She married the persona of childhood innocence and adult sex appeal by maintaining that she'd remain a virgin until marriage, while posing in a bra and short shorts on Rolling Stone.
However, things quickly spiraled out of control. Spears had a drunken Vegas wedding and an annulment 55 hours later, married (and eventually divorced) a back-up dancer, K-Fed, after three months, and infamously spent one night in drug rehabilitation, before shaving her hair off the following evening.
Recently, Spears has quit being a judge on the X Factor because they wanted to fire her for being too normal. We're proud of you, Britney.