Britney Spears Turns 30: Our 10 Favorite Career Moments

Rolling Stone Cover

In 1999 Brit covered the popular rock mag Rolling Stone but the teen’s bare-underwear cover had parents up in arms. Come on guys – she’s holding a teletubby. It marked the first phase of the singer trying to ditch her sweet southern girl next door routine. (Remember, she’s “not that innocent”). See the cover.

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