Britney Spears. Her first serious magazine cover was shot in March 1999. You can read all about it here. Here's an awesome quote from the article:
Spears and LaChapelle both say they knew the photo would cause a bit of commotion, but they figured it was worth it. "I said to her, 'You don't want to be buttoned up, like Debbie Gibson,' " LaChapelle recalls. "I said, 'Let's push it further and do this whole Lolita thing.' She got it."
Did she ever!

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