For decades, he was the pipe-smoking, silk-pajama-wearing center of a constant fantasy party at the Playboy mansion in Chicago and then in Los Angeles.
Playboy was founded more than 60 years ago and is now published in more than 20 countries across the world.
Hefner's son and chief creative officer of Playboy Enterprise, Cooper Hefner, said, "My father lived an exceptional and impactful life as a media and cultural pioneer leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom."
The first issue of Playboy was published in December 1953 and the now standard "Playboy interview" debuted in 1962. Hefner built a brand that defined the sexual culture of the second half of the 20th century.
In 1980, Hefner championed the reconstruction of the iconic Hollywood sign and was honored with a star on the Hollywood Walk of Fame.
He is survived by his wife, Crystal, his sons, Cooper, David and Marston and his daughter Christine.
Multiple celebrities took to Twitter to react to the news:
Rest in peace #HughHefner - he will forever be remembered as the Hollywood legend who lived life to the fullest.