7. Ashlee Simpson
First introduced to the world as the little sister of the famed singer Jessica Simpson, Ashlee first sought an acting career which paid off when she played Cecilia Smith in forty episodes of 7th Heaven. Afterwards, she followed in her sister’s footsteps, by both releasing an album and starring in a reality show. Certified platinum several times over, her music career, unfortunately, is mostly remembered today for an embarrassing incident where she was caught lip-synching on SNL. Caught by a paparazzi’s camera, this shot features the former pop star in the water with friends as her bikini top slides down, revealing the top half of her nipple.
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