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Los Angeles — 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.

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.”

Playboy proved a scourge, and a temptation. Drew Barrymore, Farrah Fawcett and Linda Evans are among those who have posed for the magazine. Several bunnies became celebrities, too, including singer Deborah Harry and model Lauren Hutton, both of whom had fond memories of their time with Playboy. One bunny turned out to be a journalist: Feminist Gloria Steinem got hired in the early 1960s. and turned her brief employment into an article for Show magazine.

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