Playboy founder Hugh Hefner, an advocate for the sexual revolution, is dead at 91. But the debates he embodied about sex and American liberalism are very much alive.

On some major social issues, Hefner was early to take what today are mainstream progressive stances. As my Washington Post colleague Derek Hawkins noted, Hefner was an early and avid defender of the gay rights movement, arguing that sexual liberation had to include gay people, too, in order for it to be meaningful. The same instincts led Hefner to publish extensive coverage of the emerging AIDS epidemic, recognizing that a sexually transmitted disease had no sexual orientation.

Hefner threw racially integrated parties in decades when it was not always popular to do so. Playboy picked its first black Playmate in 1965. And his magazine helped jump-start the writer Alex Haley’s career by asking him to interview Miles Davis. Playboy then gave Haley an entire series, which eventually would include important interviews with Malcolm X and the Rev. Martin Luther King Jr.

And Playboy and Hefner backed the Kinsey Institute’s research into sex, reproductive rights and the Equal Rights Amendment for women.

Of course, these are the parts of Hefner’s sexual revolution that fit neatly together. If it’s important to you to be able to have sex with large numbers of women without necessarily entering a long-term monogamous relationship, then of course it’s in your interest that women be economically independent enough not to rely on a spouse. If you want to be able to have a lot of sex without having a family, then it’s critical that you and your partners have access to contraception and the ability to legally and safely terminate any unwanted pregnancy.

If you want to do all of these things while maintaining your health and without people thinking that there’s something wrong with you, then prompt medical responses to sexually transmitted disease outbreaks and research into human sexuality that normalizes previously stigmatized behavior are obviously to your advantage. And if, above all, you venerate the pursuit of a good time, why wouldn’t you want to party with, talk to, be entertained by and read writing by the most interesting, talented people around, regardless of their race, sexual orientation or gender identity?

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But not every tension inherent in sexual liberation is so easily resolved.

Hefner may have advocated for women’s equality and independence in the political sphere. But that ideal state of affairs never arrived in Hefner’s lifetime, despite his advocacy for it. And Hefner’s own relationships were not necessarily defined by an equal balance of power. Holly Madison, who for a time was one of Hefner’s coterie of companions at the Playboy Mansion, has described an isolating curfew that prevented her from working outside of the home she shared with Hefner. And during the first year of the reality series about Hefner’s life with Madison and his other girlfriends, she maintains that the women weren’t paid for the work that they did.

In his own pajama-clad way, Hefner’s life raised the question of whether sexual liberation benefited men more than women. It’s an uneasy doubt that lingers around everything from contemporary debates about “slut-shaming” to discussions of partying and sexual assault on college campuses. The Playboy Mansion itself was allegedly one of Bill Cosby’s hunting grounds.

Even if women could participate in the sexual revolution with as much physical safety and reputational security as men, our gender politics are such that the power that comes from sexual expression still accrues differently to men and women.

I’m not sure appearing as a Playboy centerfold ever did as much for a woman as the Playboy brand itself did for Hefner: A woman can gain from being gorgeous, but she doesn’t always gain as much as the man who sleeps with her, marries her or claims to have discovered her.

And none of this is even to delve into the conundrum that Nora Ephron laid out in a 1972 essay about sexual fantasies: What happens if after sexual liberation, the sexiest and most transgressive things we can dream of are inequality and submission?

Hefner was a fixture on the American scene for so long that by the time I was old enough to know who he was, he seemed ancient, embarrassing, still peddling his shtick on comedies like “Entourage” and “The House Bunny” long after America had absorbed and distorted his ethos. But even as Hefner aged, his signature pajamas becoming more a sign of infirmity than sexual vigor, the questions and contradictions his life posed to the rest of us remain as vital – and vexing – as ever.


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