Then: Cindy Crawford (1989)
Illinois-born model Cindy Crawford, known for her all-American beauty and trademark mole, is considered one of the most popular supermodels of the 1980s and 1990s. Crawford not only walked the catwalk, she also posed for a multitude of magazines and signed big-name endorsement deals. —XFINITY Entertainment Staff (Photo: Frank Micelotta/Getty)
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