The consummate playboy outlived both the sexual revolution he fought for but also some of the famous buxom pin-ups to grace his groundbreaking magazine's center-fold.
A self-proclaimed master of marketing, Hefner skill for self-promotion made it impossible to untangle his image from his empire.
"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," his son Cooper Hefner, Playboy Enterprise's chief creative officer, 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."
Well past retirement age Hefner continued to take an active role in the editorial side of his magazine, choosing covers and Playmates each month.
Late into his life he also frequented nightclubs and maintained a bevy of young girlfriends, a lifestyle he credited with keeping him young both in and out of the bedroom.
In a 2003 interview with AFP, Hefner said he "would like to be remembered as somebody who had a positive impact on the changing social sexual values of his time."
"And I think that position is pretty well secured."
The Playboy cover that made Hugh Hefner an icon