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Britney Spears photographed by David Lachapelle for Rolling Stone, March 1999

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. She knew it would get people talking and excited.” Spears proved, even then, that she was going to take charge of crafting her own image. One night while they were shooting, LaChapelle says, Spears’ manager, Larry Rudolph, walked in at 2 a.m. to find her posing in her bra and panties. Rudolph demanded to know what was going on. “Britney said, ‘Yeah, I don’t feel comfortable,’ ” says the photographer. “At first I felt betrayed. But as soon as Larry walked out, Britney said, ‘Lock the door’ and unbuttoned her shirt wide open.”