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Photo by David LaChapelle, Matthew Rolston, and Peggy Sirota

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Britney Spears, 1999

A then-17-year-old Britney Spears sports hot pants and clutches a Teletubby for her first cover, shot when "...One More Time" was dominating the charts. Spears' Rolling Stone covers chronicle her career's rise, fall and comeback.

Read the Britney Spears issue of Rolling Stone from April 15, 1999.

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