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3. Jessica Biel

Gear, 2000

Jessica Biel was actively trying to shed her goody goody, 7th Heaven image when she posed topless on the cover of Gear at the age of 17. The racy photoshoot did the trick, but Biel now calls the episode one of her biggest regrets. "That photoshoot was just a really bad decision on my part and I got myself involved with people who weren't thinking about me and were instead thinking about what kind of a story they could get out of it," she later told EW.