Hugh Hefner, the founder of Playboy magazine and American icon, passed away peacefully today of natural causes at his Playboy Mansion surrounded by loved ones.

The larger-than-life entrepreneur was 91, and leaves behind an indelible legacy. Founding Playboy in 1953, Hefner turned it into the largest selling men’s magazine and broke down conservative social norms, promoting sexual freedom, in the process.

So popular was the Playboy concept that it sold 50,000 copies of its first edition, with Marilyn Monroe on the cover. Then, within 12 months circulation had grown to 200,000, and within five years it had surpassed Esquire magazine, selling close to 1 million copies a month. By the time Penthouse and Hustler began competing for market share in the early 70s, Hefner had amassed a readership of more than 7 million.

He appointed his daughter Christie as CEO of Playboy Enterprises in 1988 and stayed on as the magazine’s editor. Competition in both print and online played a part in the decline of Playboy’s sales in the 90s and noughties, and by the time the magazine’s 50th anniversary rolled around in 2004, its circulation was less than half what it had been in the 1970s. In 2009, Christie Hefner stepped down from the top job and was replaced by Scott Flanders, before Hefner privatised the company.

The process then began to transform Playboy into a brand-management company, and Pamela Anderson was the last woman to pose nude for the glossy in 2015, as Hefner realised full-frontal nudity was outdated with the advent of freely accessible internet pornography. Despite the hurdles, the businessman built a multimedia empire and amassed a fortune estimated to be worth more than $US40 million all from his kitchen table, after raising start-up capital from investors including his mother.

"My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom," says Cooper Hefner, Chief Creative Officer of Playboy Enterprises. "He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognisable and enduring in history. He will be greatly missed by many, including his wife Crystal [!harris!], my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises,".