BEVERLY HILLS—Hugh Hefner, magazine publisher, businessman, former journalist for Esquire magazine, and, most notably, the founder of Playboy magazine (and a playboy himself), died at his residence, The Playboy Mansion, in Holmby Hills on Wednesday, September 27 at the age of 91. According to reports, Hefner’s death was the result of natural causes.

He was a native of Chicago. He served in the U.S. Army from 1944-1946 and earned a Bachelor’s Degree in psychology at the University of Illinois at Urbana-Champaign, where he graduated in 1949.

Hefner founded Playboy in 1953. The first issue, published in December 1953, featured a nude photo of late actress Marilyn Monroe from a 1949 calendar shoot. Since its development nearly 65 years ago, the Playboy franchise inherited millions over the following decades and has become one of the most iconic, well-known, top-selling brands in the world.

In 1963, Hefner was incarcerated for “selling obscene literature.” That was, at the time, nude photos of Jayne Mansfield. The case was dropped, after which Hefner created the Playboy Foundation to help fund human sexuality research and fight censorship.

In the 1970s hit, Hefner and Playboy entered competition with other men’s magazines, including Penthouse. In the January 1972 issue, Marilyn Cole posed full-frontally nude on the cover; this creation was allegedly in response to the development of Penthouse and other publications which began pursuing hardcore pornographic content.

The highest selling edition of Playboy was the November 1972 issue, which featured Lena Soderberg on the cover.

Hefner suffered a stroke he experienced in 1985, just before his 59th birthday. After the stroke, he reportedly decided to dampen the intensity of his popular Playboy Mansion parties.

His daughter, Christie, took over as CEO the Playboy Enterprises in 1988. Twenty-one years later, in 2009, Scott Flanders replaced her and began transitioning the company’s focus on branding and licensing.

Hefner was married three times, first to his high school sweetheart, Mildred Williams, in 1949. They had two children, Christie and David. He wed Kimberly Conrad, then Playmate of the Year and 36 years his junior, in 1989. Hefner and Conrad had two sons, Marston and Cooper. He married his third wife (now widow), Crystal Harris (60 years his junior) on New Year’s Eve 2012, approximately a year and a half after Harris ended their first engagement just days before their planned wedding in June 2011.

Hefner featured numerous well-known female figures on the covers of Playboy such as Pamela Anderson, Kim Basinger, Carmen Electra, Cindy Crawford, Drew Barrymore, Olivia Munn, and Kim Kardashian. Hefner also had a long list of girlfriends, Holly Madison and the Shannon Twins (Karissa and Kristina) being a few of the most notable. His youngest son, Cooper, is the current Chief Creative Officer of Playboy Enterprises.

“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. 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,” said Cooper in a statement.

Hefner is survived by his children Christie, Marston, Cooper and David.