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This former beauty queen from St. Other hot single female inmates might be interested in something more — possibly true love. The Editors of Men's Health The editors of Men's Health are your personal conduit to the top experts in the world on all things important to men: But the faces to break a thousand hearts deserve our applause and more, especially considering that these women are actresses, singers, models and bona fide businesspeople. Which is a real cultural anomaly, considering her CV. That led to roles in Taxi Driver, as well as the sitcoms Moonlighting and Cybill, which eventually earned Shepherd three Golden Globe awards. Down, Kitty.

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In later years, her status as a fashion icon—she was a favorite of designer Hubert de Givenchy—threatened to overshadow her considerable acting career:

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While Gigi got a head-start in the modelling career, Bella is hot on her tracks — just with a slightly different career path. As one inmate puts it, "Even the best of people make mistakes right? You pay them bills, Nicky and keep us watching. Down, Kitty. Sure, Jenna Jameson is a household name, and other San Fernando Valley starlets occasionally pop up in mainstream Hollywood productions, but Sasha Grey may be the first true star to cross over from the realm of porn.

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