Playboy founder Hugh Hefner has died aged 91.
The American magazine publishing titan died at the Playboy Mansion in Los Angeles.
Hefner was born on April 9, 1926 in Chicago, Illinois, and went on to become a millionaire after founding the influential men's magazine in 1953.
Playboy Enterprises said Hefner had built the company into one of the most global brands in history.
A statement from Playboy said Hefner died "peacefully" and "from natural causes" at The Playboy Mansion. He was "surrounded by loved ones".
Hefner is survived by his wife Crystal, four grown children, Christie, who served as CEO of Playboy Enterprise for more than 20 years, David, Marston and Cooper, who currently serves as Chief Creative Officer at the company, Playboy said.
"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," 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, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises."
People took to Twitter to share their condolences.
Hefner was born Hugh Marston Hefner in 1926 and grew up in a strict Methodist family.
He signed up to the Army during the Second World War, and drew cartoons for Army newspapers until his honorable discharge in 1946, according to Daily Mail.
Despite his family's conservatism, his mother gave him a US$1,000 loan to publish Playboy - "Not because she believed in the venture but because she believed in her son."
The magazine hit with a splash, featuring a nude Marilyn Monroe on the cover, and went on to become one of America's most famous publications.
Hefner sold his iconic mansion last year for close to US$100 million ($138m) to his next door neighbour.
The Playboy founder, 90 at the time, was allowed to live there until he died.
Hefner still owned 20 per cent of the business that published Playboy magazine and remained editor in chief of it to this day, the Wall Street Journal reports.
The magazine, which Hefner's youngest son Cooper is the chief creative officer of, put naked women back in its pages in February, ending a year-long ban on the nudity which first made it famous.
The 63-year-old magazine had banished naked women from its print edition because it felt the content had become passed in an era of online porn that is just a click away on personal computers and smartphones.
- additional reporting news.com.au, Daily Mail