Hugh Hefner turned silk pajamas into a work uniform, women into centerfolds and sexual desire into a worldwide multimedia empire that spanned several generations of American life. With Playboy, he helped slip sex out of the confines of plain brown wrappers and into mainstream conversation.

In 1953, a time when states could legally ban contraceptives and the word “pregnant” was not allowed on “I Love Lucy,” Hefner published the first issue of Playboy, featuring naked photos of Marilyn Monroe and an editorial promise of “humor, sophistication and spice.” The Great Depression and World War II were over and Playboy soon became forbidden fruit for teens and a bible for men with time and money, primed for the magazine’s prescribed evenings of dimmed lights, hard drinks, soft jazz, deep thoughts and deeper desires. Within a year, circulation neared 200,000. Within five years, it had topped 1 million.

 

Hefner, the pipe-smoking embodiment of the lifestyle he touted, died at his home of natural causes on Wednesday night, Playboy said in a statement. He was 91. Hefner and Playboy were brand names worldwide. Asked by The New York Times in 1992 of what he was proudest, Hefner responded: “That I changed attitudes toward sex. That nice people can live together now. That I decontaminated the notion of premarital sex. That gives me great satisfaction.” By the 1970s, Playboy magazine had more than 7 million readers and had inspired raunchier imitations such as Penthouse and Hustler. Competition and the internet reduced circulation to less than 3 million by the 21st century, and the number of issues published annually was cut from 12 to 11. In 2015, Playboy ceased publishing images of naked women, citing the proliferation of nudity on the internet but restored its traditional nudity earlier this year.

Hefner was an ongoing advertisement for his own product, the pipe-smoking, silk-pajama-wearing center of an A-list, X-rated party. By his own account, Hefner had sex with more than a thousand women, including many pictured in his magazine. One of rock ‘n’ roll’s most decadent tours, the Rolling Stones shows of 1972 featured a stop at the Hefner mansion.

 

 

Throughout the 1960s, Hefner left Chicago only a few times. In the early 1970s, he bought the second mansion in Los Angeles, flying between his homes on a private DC-9 dubbed “The Big Bunny,” which boasted a giant Playboy bunny emblazoned on the tail. Hefner was host of a television show, “Playboy After Dark,” and in 1960 opened a string of clubs around the world where waitresses wore revealing costumes with bunny ears and fluffy white bunny tails. In the 21st century, he was back on television in a cable reality show — “The Girls Next Door” — with three live-in girlfriends in the Los Angeles Playboy mansion. Network television briefly embraced Hefner’s empire in 2011 with the NBC drama “The Playboy Club,” which failed to lure viewers and was canceled after three episodes.

Censorship of the magazine was inevitable. Playboy has been banned in China, India, Saudi Arabia and Ireland. In the 1950s, Hefner successfully sued to prevent the U.S. Postal Service from denying him second-class mailing status. 7-Eleven stores for years did not sell the magazine. Stores that did offer Playboy made sure to stock it on a higher shelf. He wasn’t only condemned by conservatives. Many feminist and regarded him as a glorified pornographer who degraded and objectified women with impunity. Women were warned from the first issue: “If you’re somebody’s sister, wife, or mother-in-law,” the magazine declared, “and picked us up by mistake, please pass us along to the man in your life and get back to Ladies Home Companion.”

 

By then Hefner had built a $200 million company by expanding Playboy to include international editions of the magazine, casinos, a cable network and a film production company. In 2006, he got back into the club business with his Playboy Club at the Palms Casino in Las Vegas. A new enterprise in London followed, along with fresh response from women’s groups, who protested the opening with cries of “Eff off Hef!”

After the stroke, Hefner handed control of his empire to his feminist daughter, Christie, although he owned 70 percent of Playboy stock and continued to choose every month’s Playmate and cover shot. Christie Hefner continued as CEO until 2009. He also stopped using recreational drugs and tried less to always be the life of the party. He tearfully noted in a 1992 New York Times interview: “I’ve spent so much of my life looking for love in all the wrong places.” Not surprisingly, Hefner’s marriage life was also a bit of a show. In 1949, he married Mildred Williams, with whom he had two children. They divorced in 1958. In July 1989, Hefner married Kimberley Conrad, the 1989 Playmate of the Year, who was then 27. The couple also had two children.

Hefner is survived by Crystal as well as his daughter, Christie; and his sons, David, Marston and Cooper. Playboy announced no immediate funeral plans, but Hefner owned a plot in a Los Angeles cemetery next to Marilyn Monroe. He was born in Chicago on April 9, 1926, to devout Methodist parents who he said never showed “love in a physical or emotional way.”

“At a very early age, I began questioning a lot of that religious foolishness about man’s spirit and body being in conflict, with God primarily with the spirit of man and the devil dwelling in the flesh,” Hefner said in a Playboy interview in 1974. “Part of the reason that I am who I am is my Puritan roots run deep,” he told The Associated Press in 2011. “My folks are Puritan. My folks are prohibitionists. There was no drinking in my home. No discussion of sex. And I think I saw the hurtful and hypocritical side of that from very early on. ”

Hefner loved movies throughout his life, calling them “my other family.” He screened classic films and new releases at the mansion every week. Every year on his April 9 birthday, he’d run his favorite film, “Casablanca,” and invite guests to dress in the fashions of the 1940s. He long hoped to be the subject of a biopic and was helping to develop a screenplay for such a film in 2011. He was a playboy before Playboy, even during his first marriage, when he enjoyed stag films, strip poker and group sex. His bunny obsession began with the figures that decorated a childhood blanket. Years later, a real-life subspecies of rabbit on the endangered species list, in the Florida Keys, would be named for him: Sylvilagus palustris hefneri.

“Well, if we hadn’t had the Wright brothers, there would still be airplanes,” Hefner said in 1974. “If there hadn’t been an Edison, there would still be electric lights. And if there hadn’t been a Hefner, we’d still have sex. But maybe we wouldn’t be enjoying it as much. So the world would be a little poorer. Come to think of it, so would some of my relatives.”