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The Most Beautiful Celebrity Women Over 50

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18. Oprah Winfrey
Former Miss Black Tennessee Oprah Winfrey founded an empire on her intimate, entreating approach to daytime television; Tangientally, she sparked a decades-long fascination with her appearance. Thankfully, the Mississippi native is willing to share all her beauty secrets! Since 1989, Winfrey has counted on makeup artist Reggie Jones to keep her looking red carpet-ready.