FILE - In this April 7, 2006 file photo, Playboy founder Hugh Hefner is photographed at the Playboy Mansion in the Holmby Hills area of Los Angeles. Hefner has died at age 91. The magazine released a statement saying Hefner died at his home of natural causes Wednesday night, Sept. 27, 2017, surrounded by family. (AP Photo/Kevork Djansezian, File)

ANDREW DALTON,  Associated Press

LOS ANGELES (AP) – Hugh Hefner turned silk pajamas into a work uniform, women into centerfolds and Playboy magazine into a worldwide multimedia empire that spanned several generations of American life.

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 risqué 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.

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 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. 

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, Stratten’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.

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.

They separated in 1998 but she continued living next door to the Playboy mansion with their two sons. The couple divorced in 2010 and he proposed in 2011 to 24-year-old Crystal Harris, a former Playmate. Harris called off the wedding days before the ceremony, but later changed her mind and they married at the end of 2012.

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.”

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AP National Writer Hillel Italie and Entertainment Writer Sandy Cohen contributed to this report.