Playboy founder and sexual icon Hugh Hefner died Wednesday night (9-27-17) with family by his side. According to a statement from Playboy, Hefner died from natural causes.

According to CNN,

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.