Hefner made good on his image as a ladies’ man who spent the majority of his at-home time in silk pajamas and a smoking jacket. He was married from 1949 until 1959 to Mildred Williams, the mother of his daughter Christie and son David, but remained a bachelor for the next 40 years after they divorced. He, of course, had numerous girlfriends during that time, including a nine-year relationship with singer and model Barbi Benton, during which she appeared on three Playboy covers.”I told him I never dated a man over 24,” Benton recalled to People in 1980. “He told me he never dated anyone older than that either.”
Hef and Kimberley didn’t officially divorce until 2010, but they had an open relationship for years—most publicly when Hefner starred from 2005 to 2010 on E!’s The Girls Next Door with resident girlfriends Kendra Wilkinson, Bridget Marquardt and Holly Madison.After calling off their engagement at least once prior, Hefner married Crystal Harris on Dec. 31, 2012. Earlier that year he had said that son Cooper would likely carry on as the public face of Playboy in his stead. A private equity firm put Playboy Enterprises on sale this past April $500 million—not an indicator that Hefner’s family would no longer be involved, but rather to shore up the media corporation’s finances.