Playboy founder Hugh Hefner, the pipe-smoking hedonist who revved up the sexual revolution in the 1950s and built a multimedia empire of clubs, mansions, movies and television, symbolised by bow-tied women in bunny costumes, has died at 91.
Hefner died of natural causes at his home surrounded by family on Wednesday night, Playboy said in a statement.
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 "humour, 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.
Over his career he amassed a fortune estimated to be worth more than $US40 million and became a pop culture icon, appearing in episodes of The Simpsons, Sex and The City, and a number of his own shows.
Hefner proud of breaking taboos
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-pyjama-wearing centre of a constant party with celebrities and Playboy models.
By his own account, Hefner had sex with more than 1,000 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.
PHOTO: Hugh Hefner pictured in 1970 with girlfriend Barbi Benton and Playboy Bunny Cheri. (AP (file photo))
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 embraced Hefner's empire in 2011 with the NBC drama The Playboy Club, which failed to lure viewers and was cancelled after three episodes.
Magazine a lightning rod for controversy
Playboy's success led to many celebrities, including Drew Barrymore, Farrah Fawcett and Linda Evans, posing for the magazine, while also turning some models into celebrities, including singer Deborah Harry and model Lauren Hutton.
But it was not all smooth sailing.
Censorship was inevitable, starting in the 1950s, when Hefner successfully sued to prevent the US Postal Service from denying him second-class mailing status.
And some models had traumatic experiences, with several alleging they had been raped by Hefner's close friend Bill Cosby, who faced dozens of such allegations.
Hefner issued a statement in late 2014 he "would never tolerate this behaviour", but two years later, former bunny Chloe Goins sued Cosby and Hefner for sexual battery, gender violence and other charges over an alleged 2008 rape.
One bunny turned out to be a journalist — feminist Gloria Steinem got hired in the early 1960s and turned her brief employment into an article for Show magazine that described the clubs as pleasure havens for men only.
"Women are the major beneficiaries of getting rid of the hypocritical old notions about sex," Hefner responded.
"Now some people are acting as if the sexual revolution was a male plot to get laid."
Hefner added that he was a strong advocate of First Amendment, civil rights and reproductive rights and that the magazine contained far more than centrefolds.
Party winds down after stroke
In 1985 Hefner suffered a mild stroke and handed control of his empire to his feminist daughter, Christie, although he owned 70 per cent of Playboy stock and continued to choose every month's Playmate and cover shot. Christie Hefner continued as CEO until 2009.
He also stopped using recreational drugs and tried less to always be the life of the party.
He tearfully noted in a 1992 New York Times interview: "I've spent so much of my life looking for love in all the wrong places."
Not surprisingly, Hefner's marriage life was also a bit of a show.
In 1949, he married Mildred Williams, with whom he had two children. They divorced in 1958. In July 1989, Hefner married Kimberley Conrad, the 1989 Playmate of the Year, who was then 27. The couple also had two children.
On the eve of his marriage, Hefner was asked if he would have a bachelor party.
They separated in 1998 but she continued living next door to the Playboy mansion with their two sons.
The couple divorced in 2010 and he proposed in 2011 to 24-year-old Crystal Harris, a former Playmate. Harris called off the wedding days before the ceremony, but changed her mind and they married at the end of 2012.
"Maybe I should be single," he said a few months later. "But I do know that I need an ongoing romantic relationship.
He acknowledged, at age 85, that "I never really found my soulmate".
PHOTO: Playboy founder Hugh Hefner at The House Bunny movie premiere with Holly Madison and Bridget Marquardt. (Reuters: Fred Prouser)
'Puritanical' upbringing a driving force
Hefner was born in Chicago on April 9, 1926, to devout Methodist parents who he said never showed, "love in a physical or emotional way".
"At a very early age, I began questioning a lot of that religious foolishness about man's spirit and body being in conflict, with God primarily with the spirit of man and the Devil dwelling in the flesh," Hefner said in a Playboy interview in 1974.
"Part of the reason that I am who I am is my puritan roots run deep," he told AP in 2011.
His bunny obsession began with the figures that decorated a childhood blanket.
And when Hefner was nine, he began publishing a neighbourhood newspaper, which he sold for a penny a copy.
Being rejected by a girl he had a crush on when he was 16 proved to be a defining moment, leading to him reinventing himself into the man he became.
He began referring to himself as Hef instead of Hugh, learned the jitterbug and began drawing a comic book, "a kind of autobiography that put myself centre stage in a life I created for myself," he said in a 2006 interview with AP.
Those comics evolved into a detailed scrapbook Hefner would keep throughout his life.
It spanned more than 2,500 volumes in 2011— a Guinness World Record for a personal scrapbook collection.