Hugh Hefner Dead at 91; Playboy Founder and Publishing Legend … – E! Online

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.”

Hefner gave an interview from a rotating bed in 1968

Playboy Enterprises expanded to include, off and on over the years, television, film, resorts, nightclubs, products, a philanthropic arm and, ultimately, a number of websites, the brand always recognizable thanks to its signature logo—the silhouette of the head of a dapper, bow-tie-wearing rabbit.

In 1971, Playboy was selling 7 million copies a month, but competition had started to arrive in the form of Penthouse, with its “Penthouse Pets,” and in 1974 Larry Flynt‘s Hustler debuted. At first Playboy dabbled in more graphic photos, but eventually returned to its more intellectual, skin-with-a-purpose roots and doubled down on signature features and photo series.

Meanwhile, Hefner moved permanently to his Playboy Mansion in L.A. in 1974 and got involved in local affairs and civic projects, such as the restoration of the Hollywood sign. A minor stroke prompted a reassessment of his lifestyle, to a certain extent. He married longtime girlfriend Kimberley Conrad in 1989 and they had two sons together, Marston and Cooper.

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