The bathrobe-and-pipe stereotype was just a weird disguise for a shy Midwesterner

As we all know, most red-blooded American males purchased Playboy magazine for the articles. This is a good thing because its publisher, Hugh Hefner, who died at his Beverly Hills home yesterday at age 91, was renowned for paying his writers top wages and then backing away to allow them the freedom to create. Nice to know he got his money’s worth, in other words.
He was the exemplar of what he called the “Playboy Philosophy”. Here he is parrying with the pompous, sneering William F. Buckley Jr. on The Firing Line in 1966.

Contrary to his image as a pajama-wearing, pipe-smoking lounge lizard preying on women—a pose that grew more ridiculous as he got older, of course—“Hef” walked the First Amendment walk. Starting in 1953, he opened his Chicago-based magazine to issues that most other magazines chose to ignore or soft pedal, including civil rights, abortion rights, women’s rights, gay rights, drug legalization, censorship and, two decades before anyone else, the hidden lives of transgender people.

In 1995, in fact, he published an article called “Death of a Deceiver” by Erick Konigsberg that detailed the life and brutal death of Brandon Teena, a transgender man in Nebraska whose story inspired the movie Boys Don’t Cry.

Among the writers whose work appeared in Playboy’s pages were such literary giants as Margaret Atwood, Kurt Vonnegut Jr., Jack Kerouac, Joyce Carol Oates, Gabriel Garcia Marquez, James Jones, Vladimir Nabokov, Haruki Murakami, James Baldwin, Doris Lessing, Joseph Heller, Arthur C. Clarke, Ray Bradbury (who serialized his novel Fahrenheit 451 in the magazine), and Norman Mailer.

Please Kill Me’s resident Hef, Legs McNeil, knew Mailer well.

“Norman was grateful to Hefner, not just for publishing his work but for publishing the work of a number of talented writers,” McNeil said. “He held Hefner in high regard, because he was always decent to him. Plus, all these writers needed Hefner’s higher wages in order to make their alimony payments.”

Playboy not only paid well, they sent writers on expensive junkets. For example, they sent Mailer to Zaire in 1974 to cover the heavyweight boxing match between George Foreman and Muhammad Ali, known as “Rumble in the Jungle.” The resultant Playboy article was expanded into Mailer’s book The Fight which, in turn, partly inspired Leon Gast’s Oscar-winning documentary 1996 film When We Were Kings.

“Norman’s reportage in the 1960s and 1970s was among his finest work,” said McNeil. “And he was glad to have an outlet like Playboy that would run it.”

In addition to the art and writing, many of the interviews in Playboy were the sort of no-holds-barred slugfests you simply did not find elsewhere. Such notoriously cranky and unpredictable figures as Miles Davis, Stanley Kubrick, Marlon Brando and Bette Davis held forth in the magazine’s pages. Davis famously took on abortion and gays in her conversation, saying, “I believe abortion is better than having 10,000,000 children you can’t support… When I was a child, born in 1908, education taught you that your destiny was to marry and have children. Just because you’re a woman — but that is not your destiny.” About her status as a gay icon, Davis said, “Homosexuals are probably the most artistic and appreciative human beings, who worship films and theater… Generally, homosexuals are very appreciative of serious work in the arts, so it’s highly complimentary to be someone they choose.”

But perhaps the most haunting voice was that of Martin Luther King, Jr. in 1965.
Dr. King told Playboy, “If I were constantly worried about death, I couldn’t function. After a while, if your life is more or less constantly in peril, you come to a point where you accept the possibility philosophically. I must face the fact, as all others in positions of leadership must do, that America today is an extremely sick nation, and that something could well happen to me at any time. I feel, though, that my cause is so right, so moral, that if I should lose my life, in some way it would aid the cause.”

Years ago, I wrote a book about the artist Charles Bragg, who regularly contributed his illustrations to Playboy—and was ecstatic to get the work. Charlie told me that he would occasionally be invited over to Hefner’s mansion for one of the film screenings the magazine publisher hosted. (Hefner was a major cineaste). Hef would come out and greet his guests, often sporting the familiar costume of a bathrobe and toting his pipe prop. He would say a few words before lights went down and the film was screened, and then he would disappear, like Jay Gatsby, into the mists of a lifestyle that his uncomplaining guests could only fantasize about.

This short clip reveals Hefner’s “empire” in Chicago in the early days of the 1960s.

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