He was compared to Jay Gatsby, Citizen Kane and Walt Disney, but Mr. Hefner was his own production. He repeatedly likened his life to a romantic movie; it starred an ageless sophisticate in silk pajamas and smoking jacket hosting a never-ending party for famous and fascinating people.
Long after other publishers made the nude “Playmate” centerfold look more sugary than daring, Playboy remained the most successful men’s magazine in the world. Mr. Hefner’s company branched into movie, cable and digital production, sold its own line of clothing and jewelry, and opened clubs, resorts and casinos.
The brand faded over the years, its flagship magazine’s circulation declining to less than a million.
Mr. Hefner remained editor in chief even after agreeing to the magazine’s startling (and, as it turned out, short-lived) decision in 2015 to stop publishing nude photographs. In 2016, he handed over creative control of Playboy to his son Cooper Hefner. Playboy Enterprises’ chief executive, Scott Flanders, acknowledged that the internet had overrun the magazine’s province.
The first issue of Playboy was published in 1953, when Mr. Hefner was 27, a new father married to, by his account, the first woman he had slept with. He had only recently moved out of his parents’ house and left his job at Children’s Activities magazine. But in an editorial in Playboy’s inaugural issue, the young publisher purveyed another life: