LOS ANGELES (AP) — Playboy founder Hugh M. Hefner, the pipe-smoking hedonist who revved up the sexual revolution in the 1950s and built a multimedia empire of clubs, mansions, movies and television, symbolized by bow-tied women in bunny costumes, has died at age 91.

Hefner died of natural causes at his home surrounded by family on Wednesday night, Playboy said in a statement.

As much as anyone, Hefner 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, when the word “pregnant” was not allowed on “I Love Lucy,” Hefner published the first issue of Playboy, featuring naked photos of Marilyn Monroe (taken years earlier) and an editorial promise of “humor, sophistication and spice.” The Great Depression and World War II were over and America was ready to get undressed.

Playboy soon became forbidden fruit for teenagers 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.

By the 1970s, the magazine had more than 7 million readers and had inspired such raunchier imitations 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 temporarily ceased publishing images of naked women, citing the proliferation of nudity on the internet but restored its traditional nudity earlier this year.

Hefner and Playboy remained 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.”

Hefner ran Playboy from his elaborate mansions, first in Chicago and then in Los Angeles, and became the flamboyant symbol of the lifestyle he espoused. For decades he was the pipe-smoking, silk-pajama-wearing center of a constant party with celebrities and Playboy models. 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.

By 1988, 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!’”

Hefner liked to say he was untroubled by criticism, but in 1985 he suffered a mild stroke that he blamed on the book “The Killing of the Unicorn: Dorothy Stratten 1960-1980,” by filmmaker Peter Bogdanovich. Stratten was a Playmate killed by her husband, Paul Snider, who then killed himself. Bogdanovich, Stratton’s boyfriend at the time, wrote that Hefner helped bring about her murder and was unable to deal with “what he and his magazine do to women.”

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.