After starting the status quo-shattering Playboy magazine in 1953, Hefner went on to launch TV and film companies, finance documentaries and preside over the Hollywood social scene from his Jacuzzi at the mansion, a frequent location for industry events.
He was married three times and claimed to have slept with more than 1,000 women.
He had four children, Christie, who served as CEO of Playboy Enterprise for more than 20 years, David, Marston and Cooper.
His son Cooper, who currently serves as Chief Creative Officer at the company, led the tributes to the late icon, describing him as a "cultural pioneer".
“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,” said Cooper.
Hefner previously said his swinging lifestyle might have been a reaction to growing up in a repressed family where affection was rarely exhibited. "I'm never going to grow up," he said in a CNN interview when he was 82. "Staying young is what it is all about for me. Holding on to the boy and long ago I decided that age really didn't matter and as long as the ladies ... feel the same way, that's fine with me."
"I've never thought of Playboy quite frankly as a sex magazine," he told CNN in 2002. "I always thought of it as a lifestyle magazine in which sex was one important ingredient."
He created Playboy as the first stylish men's magazine and in addition he had intellectual appeal with top writers, in-depth interviews with historic figures such as Fidel Castro, Martin Luther King Jr., Malcolm X and John Lennon also were featured regularly.
"What I created came out of my own adolescent dreams of fantasies," he told CNN. "I was trying to redefine what it meant to be a young, urban unattached male."
He once declared sex to be "the primary motivating factor in the course of human history"
Playboy magazine, starting with its March 2016 issue, did away with full frontal nudity in a rebranding that would have been unimaginable in the publication's heyday.
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