Hefner founded Playboy in 1953 with $600 of his own money and built the magazine into a multimillion-dollar entertainment empire that at its 1970s peak included TV shows, a jazz festival and a string of Playboy Clubs whose cocktail waitresses wore bunny ears and cottontails.
Over the years, the legend of “Hef” only grew as he bedded hundreds of young women, married a few of his magazine’s “Playmates” and cavorted on reality TV shows with a stable of girlfriends less than a third his age.
Some critics dismissed him as a relic of a sexist era, especially in his later years, when Hefner spoke openly of his Viagra-fueled sex romps at the Playboy Mansion. But many men envied his adolescent-fantasy lifestyle.
And his pioneering magazine, his biggest legacy, may have helped the buttoned-up America of the 1950s and early 1960s loosen up a little about sex.
“I would like to be remembered as somebody who has changed the world in some positive way, in a social, sexual sense, and I’d be very happy with that,” Hefner told CNN. “I’m a kid who dreamed the dreams and made them come true.”