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Hugh Hefner, the iconic founder of Playboy, has died aged 91.
Hefner died of natural causes at his home surrounded by family on Wednesday night, Playboy said in a statement.
Born in Chicago, Illinois on April 9, 1926 to teacher parents, Hefner served as a writer for a military newspaper in the US Army during World War II.
He also worked as a copywriter for Esquire magazine before launching Playboy.
Hefner married three times, first to Mildred Williams in 1949 to whom he had two children, Christie and David.
The pair divorced in 1959 after which Hefner became famous for his pleasure-seeking, hedonistic lifestyle, admitting to being romantically involved with many of his "Playmates" - the female models featured in Playboy's centrefold.
In 1986, a year after suffering a minor stroke, Hefner married Playmate of the Year Kimberley Conrad, to which he had two sons, Marston Glenn and Cooper Bradford before the couple separated in 1998.
Hefner married for a third time in 2012 at the age of 86, to Crystal Harris, then 26.
Hefner has in recent years stepped back from public view.
In August this year, Hefner's son Cooper told the Hollywood Reporter it was "tough to watch him struggle" in his old age, adding he was "just happy it's physical and not mental".
As much as anyone, Hefner helped slip sex out of the confines of plain brown wrappers and into mainstream conversation.
In 1953, a time when states could legally ban contraceptives, when the word "pregnant" was not allowed on "I Love Lucy," Hefner published the first issue of Playboy, featuring naked photos of Marilyn Monroe (taken years earlier) and an editorial promise of "humor, sophistication and spice." The Great Depression and World War II were over and America was ready to get undressed.
Playboy soon became forbidden fruit for teenagers and a bible for men with time and money, primed for the magazine's prescribed evenings of dimmed lights, hard drinks, soft jazz, deep thoughts and deeper desires. Within a year, circulation neared 200,000. Within five years, it had topped 1 million.
By the 1970s, the magazine had more than 7 million readers and had inspired such raunchier imitations as Penthouse and Hustler. Competition and the internet reduced circulation to less than 3 million by the 21st century, and the number of issues published annually was cut from 12 to 11. In 2015, Playboy ceased publishing images of naked women, citing the proliferation of nudity on the internet.
But Hefner and Playboy remained brand names worldwide.
Asked by The New York Times in 1992 of what he was proudest, Hefner responded: "That I changed attitudes toward sex. That nice people can live together now. That I decontaminated the notion of premarital sex. That gives me great satisfaction."
Hefner ran Playboy from his elaborate mansions, first in Chicago and then in Los Angeles, and became the flamboyant symbol of the lifestyle he espoused. For decades he was the pipe-smoking, silk-pajama-wearing center of a constant party with celebrities and Playboy models. By his own account, Hefner had sex with more than a thousand women, including many pictured in his magazine. One of rock n' roll's most decadent tours, the Rolling Stones shows of 1972, featured a stop at the Hefner mansion.
Throughout the 1960s, Hefner left Chicago only a few times. In the early 1970s, he bought the second mansion in Los Angeles, flying between his homes on a private DC-9 dubbed "The Big Bunny," which boasted a giant Playboy bunny emblazoned on the tail.
Hefner was host of a television show, "Playboy After Dark," and in 1960 opened a string of clubs around the world where waitresses wore revealing costumes with bunny ears and fluffy white bunny tails. In the 21st century, he was back on television in a cable reality show — "The Girls Next Door" — with three live-in girlfriends in the Los Angeles Playboy mansion. Network television briefly embra
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