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Even in death, Hugh Hefner—who died in late September at the age of 91—continues to be a creep. As he arranged way back in 1992, he’ll be buried next to Marilyn Monroe, whose nude photos he published without her consent or knowledge in the first issue of Playboy. The male-gazer in chief sleeps eternally next to the world’s most fetishized sex object. The ancient toad who bullied a harem of grossed-out would-be starlets rests beside the ill-used beauty who was smart, kind, well-read, didn’t have an orgasm until the end of her life, and described herself as a “sexless sex goddess.” If only Marilyn could get up and go lie down next to someone else. Ad Policy

Looking back, it seems incredible that Playboy was ever taken for a liberatory text, even in the stodgy 1950s. “Can man be free if woman be a slave?” the poet Shelley asked in 1818. Hefner’s answer was: Absolutely—that’s the whole point! Instead of (or in addition to) a graying, aproned wife, three kids, a boring job, and a mortgage, you could, as Hefner described the Playboy life in the first issue, “enjoy mixing up cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph, and inviting in a female acquaintance for a quiet discussion on Picasso, Nietzsche, jazz, sex.” You might say that Hefner invented the toxic bachelor. Left unmentioned: You’ve still got that boring job, even if, like Hefner, you ditched the wife and kids. If you go by the ads—cars, stereos, liquor—being a playboy involved making a lot of upscale purchases. Also, poor Nietzsche. His fans are just the worst.

Playboy published important fiction and reportage in its day, whether to give adults an excuse to buy the magazine, or to fill out the fantasy of “sophistication” as a (largely successful) bid for cultural respectability. Back in the day, its libertarianism extended to support for civil rights, abortion rights, and free-speech issues, which gained it many friends among the kind of people who read The Nation. Indeed, in 2015 our own Victor Navasky won a lifetime-achievement award from the Hugh M. -Hefner Foundation. The list of judges and awardees is like an honor roll of the progressive great and good. Zephyr Teachout! Who knew.

The stumbling block, of course, was feminism. Gloria Steinem went undercover as a bunny at Hefner’s New York Playboy Club and exposed the many indignities of the job. “Hugh Hefner is my enemy,” said Susan Brownmiller when she appeared with Hefner on The Dick Cavett Show in 1970, and the feeling was definitely mutual. “These chicks are our natural enemy,” Hefner wrote in an internal memo. “They are unalterably opposed to the romantic boy-girl society that Playboy promotes.” How half-naked waitresses dressed in rabbit costumes and cartoons showing rape as lighthearted fun serve to promote a “romantic boy-girl society” is hard to explain. But then so are the many dark episodes of life in the Playboy Mansion: In 2014, Judy Huth filed a lawsuit claiming that Bill Cosby sexually assaulted her in the mansion in 1974, when she was 15 years old; a former valet is now telling the tabloids about late-’70s “pig nights,” in which Hefner’s male friends were serviced by prostitutes. The valet also recounted instances in which Hefner—more than once!—abandoned bunnies at the hospital when their breast implants burst. In her tell-all memoir Down the Rabbit Hole, Holly Madison—one of the very young Hefner “girlfriends” featured on the reality show The Girls Next Door—painted a harrowing picture of her time in the mansion. The women living there had a 9 pm curfew and were constantly degraded and belittled, and sex with Hefner was mandatory. Even fellow next-door girl Kendra Wilkinson, who presented a much more positive version of events in her own memoir, admitted that “I had to be very drunk or smoke lots of weed to survive those nights—there was no way around it.” You have to ignore a lot of human suffering to buy the notion that “Hef” was a fun-guy genius who brought us sexual liberation. “Why lionize Hugh Hefner, a pig, a pornographer & a predator too?” Bette Midler tweeted. “I once went to the ‘mansion’ in ’68 and got the clap walking thru the door.”

What brought us whatever sexual liberation we now possess was reliable contraception, legal abortion, and, yes, feminism. It was feminism that encouraged women to consider their own pleasure, cut through the Freudian nonsense about vaginal orgasms and “frigidity,” mainstreamed female masturbation as a way to learn about one’s body, and pointed out, insistently, that women are not objects for male consumption. That last one seems a little quaint now that the most hard-core porn—stuff that makes Playboy centerfolds look like Victorian valentines—is just a click away, and important feminist thinkers and activists seem unable to say that this isn’t a good thing. It’s easier to wave away the critics of porn as Dworkinite killjoys and prudes and talk some more about freedom of speech.

Actually, Andrea Dworkin had a point about pornography (a category in which she would have included Playboy) not being great for women’s equality or pleasure. Her big mistake—one of them, anyway—was to think that it could be outlawed. Even if there were no First Amendment, porn is simply too popular, too profitable, and, especially now thanks to the Internet, too pervasive for a democratic society to proscribe it—even if we could agree on what it was. Related Article The Lives and Deaths of ‘The Village Voice’ Leslie Savan

We rightly use the First Amendment to defend expression, but “it’s legal” isn’t the last word on whether it has value. After we invoke the importance of free speech—and the courts, in their wisdom, have declared many things speech that don’t involve words, like stripping and flag burning and (we’ll see) baking cakes—we can still critique the actual content. Does it enlarge our perspective, does it make for wisdom, is it just or beautiful, does it help us to be better people, more interesting, or even just more amusing? Why is it so hard to ask what kind of a world we make when we hail as heroic a man who saw women as a pair of implanted breasts with a sell-by date of their 25th birthday? It’s a conversation that Hugh Hefner did a great deal to suppress. It’s too late for Marilyn, but not for us. Now that he’s dead, let’s talk.