Hugh Hefner
via Instagram / Hugh Hefner

A legend and icon has passed away. Playboy founder Hugh Hefner died Wednesday (Sept. 27) at his infamous Los Angeles home, the Playboy Mansion. He was 91 years old.

According to reports, Hef died from natural causes.

“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,” Hefner’s son Cooper, chief creative officer of Playboy Enterprises, said in a statement. “He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable 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.”

Hugh Hefner started Playboy in 1953 with a loan of $8,000 and has grown it into one of the most recognizable brands on the planet, with annual revenues in the hundreds of millions.

For the first issue, he purchased a picture of a naked Marilyn Monroe, taken before she was famous and put it on the cover, which hit newsstands in December 1953. It had no date, because he didn’t believe he would release future issues, but it sold 54,000 copies… and the rest is history.

Throughout the years, Hefner’s Playboy magazine featured some of entertainment’s biggest stars, all posing nude — including Barbra Streisand, Madonna, Mariah Carey, Lindsay Lohan, Kate Moss, Dolly Parton, Pamela Anderson and Drew Barrymore, among others.

In addition to its sexy pictorials, he launched the in-depth “Playboy Interview” in 1962 with an interview with jazz legend Miles Davis. Over the years, the mag has sat down with iconic figures like filmmakers Stanley Kubrick and Woody Allen, civil rights luminaries Dr. Martin Luther King Jr. and Malcolm X, and The Beatles.

Despite its legendary status in pop culture, Playboy Enterprises has had some rough times financially. It has been plagued by layoffs in the past decade, before eventually going private in 2011 after years of a declining stock prices.

In March 2016, the magazine underwent a redesign, with the announcement that it would be releasing its last nude issue, covered by Pam Anderson. However, after less than a year, it went back to its nude format.

Last year, Playboy put the infamous Mansion on the market for $200 million. It eventually sold months later for $100 million to Daren Metropoulos, the co-owner of Twinkies maker Hostess.

Hefner is known for having multiple girlfriends, but his last was Crystal Harris, who he ultimately in December 2012 when he was 86 and she was 26.