Hugh Hefner (Sept. 27, 2017, age 91)
Hefner died at his home, the Playboy Mansion near Beverly Hills. Playboy Enterprises announced the loss, citing natural causes.
Often photographed wearing his iconic silk pajamas and smoking jacket, Hef, as he was lovingly called, founded Playboy in 1953. It was an attempt to provide an outlet for the sexes to understand each other, and wanted sexuality to be more accepted in American culture.
Hef was 27-years-old at the time, a new father, and married to who he claimed was the first woman he slept with. Later in life he admitted to sleeping with “over a thousand” women. “There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn’t married,” he said in a 2013 interview with Esquire.