The late Hugh Hefner was nearly as famous for his love life as he was for founding the groundbreaking Playboy enterprise.
After first publishing the men’s entertainment magazine in 1953, he would go on to open clubs, casinos and hotels with the iconic name and logo — but the women on his arm were always just as newsworthy.
From dating models to actresses to his very own Playboy centerfolds, Hugh was soon recognized for having multiple live-in girlfriends at the Playboy Mansion.
Perhaps the most famous of these paramours were the stars of the reality show Girls Next Door: Holly Madison, Bridget Marquardt and Kendra Wilkinson. Hugh never married any of these women, though.
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