On Wednesday night, Playboy Enterprises confirmed in a press release that its founder, Hugh Hefner, had died at 91. Hefner died of natural causes, surrounded by friends and family.
"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, the chief creative officer of Playboy Enterprises, said in a statement.
Below, take a look back at the life of the legendary Hefner.
Hefner started Playboy magazine at the age of 27 years. Hefner was born on 9 April 1926.
Hefner launched Playboy magazine in 1953 with $8,000 in borrowed money. Its first issue featured Marilyn Monroe, and it sold 54,000 copies.
Throughout the 1950s and 1960s, Hefner hosted a few TV shows, including "Playboy's Penthouse," during which he would interview celebrities like Sammy Davis Jr. and Bob Newhart.
He also hosted the show "Playboy After Dark," which had various musical performers as guests. Hefner also created the Playboy Club, which had several nightclub locations.
Hefner traveled in style inside his $5.5 million private Playboy jet in the 1970s. By that time, Playboy had cemented itself as a cultural icon with its famous "Playboy Interviews," which featured subjects like Stanley Kubrick, Dr. Martin Luther King Jr., and Ayn Rand.
During the 1970s he also helped produce a few feature films, including Roman Polanski's "Macbeth."
He was active politically, including when he contributed financially to the landmark Roe v. Wade decision on abortion in 1973.
In 1974, Hefner officially moved from Chicago out to California and into the famed Playboy Mansion.
In 1977, Hefner told the Associated Press that his $200 million dollar empire "is settling down after a flamboyant youth and a tumultuous adolescence."
In 1980, he was awarded the 1,716th star on the Hollywood Walk of Fame.
Hefner had two children with his first wife, Millie Williams, in the 1950s — a daughter, Christie, and a son, David. The couple divorced in 1959, however. In 1989, Hefner married a former Playmate of the Year, Kimberly Conrad. Together, they had sons Marston and Cooper. Hefner and Conrad divorced in 2010, and Hefner married Crystal Harris in 2012.
Hefner had placed his office in his bedroom since the 1960s, but it wasn't until the 1970s, when he moved out to Los Angeles, that the famous silk robe became his signature look.
He also starred in and produced the E! reality show "The Girls Next Door," along with then-girlfriends Kendra Wilkinson, Bridget Marquardt, and Holly Madison. The show aired from 2005 until 2010.
In more recent years, the magazine and brand began to struggle. The New York Times reported in 2009 that the magazine began promising advertisers a 1.5 million circulation, down from the previously promised 2.6 million.
Playboy announced in October 2015 that it would no longer be featuring nude photos in its pages. By February 2017, however, the magazine said nude photos would be back.
Market researcher Wealth-X told Business Insider that at the time of his death, Hefner was worth at least $110 million. While it's not 100% clear who will inherit his wealth, Us Weekly reported in 2013 that Hefner's wealth would be left to "his children, the University of Southern California film school, and a variety of charities."
The Playboy Mansion is now owned by its next-door neighbor, Daren Metropoulos, a principal of the private-equity firm Metropoulos & Co. and a former co-CEO of Pabst Brewing Company. Metropoulos bought the home for $100 million in 2016.
Credit: New York Times and Pulse.
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