The 91-year-old may no longer be here, but his legacy will go down in the history books.
The pipe-smoking, pyjama-wearing polygamist was the epitome of eccentric, and he truly believed in his out-of-the-box lifestyle.
"Life is too short to be living somebody else's dream," Hef once said, and it seems these are words he lived by.
"I'm very comfortable with the nature of life and death, and that we come to an end. What's most difficult to imagine is that those dreams and early yearnings and desires of childhood and adolescence will also disappear. But who knows? Maybe you become part of the eternal whatever," he's mused of the circle of life.
From the Playboy empire he built from the ground up, to his many girlfriends, wives and flings, to the secret, more softer side of Hef - that of a family man, the millionaire mogul definitely ticked everything off his bucket list a few times over!
To celebrate the life and times of Hugh Hefner, we look back at his incredible life in pictures.