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Holly Madison

To pay her tuition, she started modeling and working at Hooters, where she caught the eye of Playboy reps. Hef invited her to the Mansion — and a year later, he invited her to move in and become his long-term girlfriend. Miss Madison starred on The Girls Next Door for five years, working as a photo editor for Playboy Magazine for two seasons of the show, with a focus on Playmate pictorials and Centerfolds. She was published in five consecutive issues of Special Editions, posed for four covers of Playboy magazine and pictorials with co-girlfriends Bridget Marquardt and Kendra Wilkinson. Her seven-year relationship with Hefner ended in , but by rights, Holly is her own celebrity, and she remains an integral member of the Playboy family.

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