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Top 15 Hottest Women Hugh Hefner Has Been With TheRichest

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Kendra, Holly & Bridgets Biggest Girls Next Door Bombshells

Best known as the head girlfriend on the Playboy reality series The Girls Next Door, Holly Madison had seniority over the other two main girlfriends. Madison began dating Hefner in 2001 while mansionmates Kendra Wilkinson and Bridget Marquardt joined up with Hefner in 2003.

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Girls Next Door Star Bridget Marquardt Breaks Silence on Hugh Hefner's Death Says She's 'Forever Grateful'

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