Hugh Hefner, the founder of Playboy magazine who turned his swinging lifestyle into a professional calling and taught Americans to be more open about sex, has died. He was 91.

Hefner died Wednesday from natural causes surrounded by friends and family at his home, the Playboy Mansion, in Los Angeles, according to a post on Playboy’s official Twitter feed and a news release published on the PR Newswire. Hefner’s wish was to be buried in a crypt he bought next to the grave of Marilyn Monroe in Los Angeles. Pictures of a nude Monroe catapulted Playboy to success with its first edition in 1953.

The direct descendant of a Puritan who arrived in America on the Mayflower, Hefner shattered traditional attitudes to sex in the 1950s and ’60s with centerfold pictorials of semi-naked women and articles on gender relations. Playboy’s celebration of the female body and redefinition of male pastimes transformed sex from a forbidden topic into dinner-table conversation.

His monthly publication with the rabbit-head trademark and photos of girl-next-door Playmates remained the U.S.’s most popular men’s magazine for four decades, driving sales for a single issue to 7 million by the early 1970s. He claimed Playboy had a profound effect on American society by advancing the cause of press freedom, racial equality and women’s rights. Critics, including many feminists, disagreed, condemning him for objectifying women.

“He was perhaps the greatest counter to the Puritan ethic we’ve ever seen,” Garth Jowett, a professor of communications at the University of Houston, said in a 2003 interview in the Houston Chronicle. “One of the greatest social forces in the 20th century in the United States was Playboy magazine.”

Designing ‘Hef’

“Hef,” as he called himself after unrequited love triggered an image makeover during his college days, became one of America’s most recognized bachelors. He spent much of his adult life with multiple live-in girlfriends, attending to work matters from his mansions in Los Angeles and Chicago.

The pipe-smoking womanizer became a symbol of the 1970s zeitgeist, bedding countless females half his age. In 1968, Hefner met actress Barbi Benton, who would remain his favorite girlfriend for much of the next decade. When Hefner, 42 at the time, asked her for a date, Benton, who was 18, said she had never been out with anyone older than 24. “That’s all right,” he replied. “Neither have I.”

Dressed in silk pajamas and a velvet bathrobe, Hefner promoted the single life with magazine tips on fashion, apartment living and entertaining. Before Playboy appeared, such topics were excluded from mainstream men’s publications, which focused on leisure activities such as hunting and sports.

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