Playboy founder Hugh Hefner has died from natural causes.
Hefner, 91, peacefully passed away at his home, Playboy Enterprises said in a statement.
The iconic playboy introduced the magazine to the public in 1953 and built the company into one of the most recognisable and quintessentially American brands.
Mr Hefner began publishing Playboy in his kitchen at home, and it was eventually shifting seven million copies a month at its peak.
"I'm never going to grow up," Mr Hefner said in a CNN interview when he was 82. "Staying young is what it is all about for me. Holding on to the boy and long ago I decided that age really didn't matter and as long as the ladies ... feel the same way, that's fine with me."
Cooper Hefner, his son, said he would be "greatly missed by many".
He described his father as a leading voice behind moves towards free speech and sexual freedom.
He started publishing the magazine from his kitchen in 1953, using money he had borrowed. At its peak, the publication was the biggest-selling men's magazine in the world, selling seven million copies a month.
Mr Hefner successfully tapped into a new generation of Americans who were enjoying rising standards of living in the boom years of the 1950s and 60s.
A political activist and philanthropist, he produced not just a magazine, but a whole lifestyle. And in Playboy's famous bow-tie-wearing rabbit he launched one of the most recognised brands of the 20th century.
'I never thought of it as a sex magazine'
Hugh Marston Hefner was born in Chicago on 9 April 1926, the son of two teachers with strong religious views.
After serving in the US Army as a writer, he graduated with a degree in psychology before going to work as a copywriter for the men's magazine, Esquire.
In 1953 he borrowed US$8000 to produce the first issue of Playboy. Hefner was so worried that the magazine would not sell that he left the date off the cover.
His mother contributed $1000.
"Not because she believed in the venture," Hefner later said, "but because she believed in her son."
He had originally planned to name the new publication Stag Party, but changed his mind at the last minute.
"Can you imagine a chain of clubs staffed by girls wearing antlers?"
The first edition featured a set of nude photographs of Marilyn Monroe that Hefner had bought for $200. They had originally been shot for a 1949 calendar.
Whether by luck or judgement, Hefner's timing was just right. The launch of Alfred Kinsey's reports on human sexual behaviour challenged conventional beliefs about sexuality and raised subjects that, until then, had been taboo.
"Kinsey was the researcher," Hefner later remarked, "I was the pamphleteer."
Middle-class American society in the 1950s was notoriously strait-laced and the combination of tastefully photographed women and intellectually stimulating articles appealed to the post-war urban male.
"I never thought of it as a sex magazine," Hefner later recalled. "I always thought of it as a lifestyle magazine in which sex was one important ingredient."
It was an unqualified success, selling more than 50,000 copies within weeks. Hefner had found a niche in the market for men's publications, which was then dominated by hunting, shooting and fishing periodicals.
The second issue saw the appearance of the bow-tie-wearing rabbit, which was designed by the magazine's art director Art Paul. It would appear on a host of products over the following decades.
In 1955 Hefner published a short story by the writer Charles Beaumont, about straight men facing persecution in a world where homosexuals were the majority.
In response to a flood of angry letters, Hefner replied: "If it was wrong to persecute heterosexuals in a homosexual society then the reverse is wrong too."
In later years he would become an advocate for same-sex marriage describing it as "a fight for all our rights".
Hefner's editorial stance was in tune with the changes in society as the magazine campaigned for liberal drugs laws and the right to abortion.
For the next 20 years, Playboy dominated its market, with circulation peaking at over seven million in the early 1970s, when a survey suggested that a quarter of all male college students in America were buying the magazine.
At the time it contained some of the finest contemporary writing in the magazine market, with Saul Bellow, Arthur C Clarke, Norman Mailer and Gore Vidal among the regular contributors.
The articles appeared sandwiched between the obligatory photographs of beautiful women, although far more tastefully shot than many of Playboy's more downmarket competitors.
The centre spread entitled Playmate of the Month featured some famous names including Jayne Mansfield and Pamela Anderson, while other celebrities, including Bo Derek, Kim Basinger, Farrah Fawcett and Madonna, have been happy to pose for the magazine.
The photographs of Jayne Mansfield provoked Hefner's arrest and a prosecution for obscenity in 1963 but the jury was unable to reach a verdict.
Hefner set out to exploit the success of his magazine with the opening of the first Playboy club in Chicago in 1960, which introduced the Playboy bunny waitresses.
The relaxation of gaming laws in the UK opened up another opportunity and Hefner opened three casinos in the UK. By 1981 they were contributing all of Playboy's worldwide profits.
At this time Hefner was living a life of luxury and indulgence in his two Playboy mansions, accompanied by an ever-changing cast of celebrities and pneumatic girlfriends, and shuttling between them in his personalised DC9, the Big Bunny.
Hefner's fortunes went into a major decline during the 1980s. The British authorities shut down the UK casinos following a series of irregularities, effectively cutting Playboy's income.
A year later a casino in Atlantic City, New Jersey, was closed after Hefner was judged by the state gaming board to be an unsuitable person to hold a licence.
Playboy magazine too was failing as more sexually explicit competitors competed for space on the newsstands and traditional readers got older and moved on.
In a further personal blow Hefner suffered a stroke in 1985 and four years later passed the daily control of Playboy Enterprises to his daughter Christie.
In 1989, at the age of 63, Hefner married one of his playmates, 27-year-old Kimberley Conrad. The marriage lasted for 10 years and produced two children.
In 2012 he married his third wife, Crystal Harris, when he was 86 - 60 years older than his bride.
A libertarian by nature, Hefner's Playboy Foundation continued to support freedom of expression and First Amendment rights. He also donated large sums of money to the Democratic Party, including Hillary Clinton's presidential campaign.
- BBC / Reuters