But today, on the eve of what would have been the centennial birthday of Playboy progenitor Hugh Hefner — and two decades into the era of ubiquitous, hardcore, high-definition internet porn that makes Playboy’s softly lit, artfully posed centerfold look positively quaint, even pre-Raphaelite, by comparison — I must grudgingly admit that the defense of the nudie magazine as literary artifact seems a lot less ridiculous than it once did. Did anyone read Playboy just for the articles? Probably not, and yet there was a time, not so long ago, when they plausibly could have. It was a golden era of great tits and great journalism, where lust and literacy still existed in conversation, rather than in conflict. 

Playboy launched in 1953 with a singular purpose, filling what its creator saw as a gap in the world of leisure reading for men. For the outdoorsman, there was no shortage of content; but for his urban counterpart? A sad state of affairs: there were but two magazines for what Hefner called “the city-bred male”, and these were woefully overstuffed with service journalism. An editorial note in the opening pages of Playboy’s first volume lamented the excessive focus on “fashion, travel, and ‘how-to-do-it’ features on everything from avoiding a hernia to building your own steam bath”, all of which came at the expense of fun. 

“PLAYBOY will emphasize entertainment,” Hefner promised. “Affairs of state will be out of our province. We don’t expect to solve any world problems or prove any great moral truths. If we are able to give the American male a few extra laughs and a little diversion from the anxieties of the Atomic Age, we’ll feel we’ve justified our existence.”

That first issue, in its time, was most notorious for featuring a pictorial of Marilyn Monroe in the nude — photos taken in 1949 before she was famous, or even a blonde. But today, the most remarkable thing about that first volume is its capacity to transport us back to a world where attention spans had not yet been decimated by the advent of the endless scroll, where a magazine might make for an afternoon’s leisure. 

The centerfold makes for a spectacular gimmick, but most of Playboy was text, and longform text at that; the inaugural issue contained three works of short fiction, journalistic dispatches from the worlds of college football and jazz music, a combination investigative report and opinion piece about alimony with the self-explanatory title, “Miss Gold-Digger”, and a recipe for Cuban chicken. There are also a number of single panel cartoons and a page of quaint, short-form japes that my grandfather would have called “dirty jokes” and a contemporary HR department would call “creating a hostile work environment”:

An elderly gentleman visited his doctor with the complaint that he believed he was becoming impotent.

“When did you first become aware of this problem?” the doctor asked.

The old gentleman replied, “Yesterday afternoon, twice last night and again this morning.”

If this all feels somewhat dated now, it was a durable journalistic model: a combination of bawdy humor, cheeky cartoons, and the ever-present centerfold sandwiched between voicey reportage and short fiction from the best storytellers of their generation. Vladimir Nabokov, Joyce Carol Oates, Ray Bradbury, John Cheever: all of these and more graced the pages of Playboy, without embarrassment. Peruse any issue at random, and it’s hard not to be impressed by the magazine’s stylistic consistency over the decades, even as its substance kept pace with the times. In June 1988, 35 years after Playboy’s debut, the world had changed but what constituted “Entertainment for Men” remained the same: jokes, cartoons, journalism, women. Here is Miss June Emily Arth, all creamy skin and sunlit hair like a John Waterhouse painting, tastefully framed by a David Foster Wallace short story on one side and satire of the upcoming presidential election on the other. 

This frank sensuality, the uncritical and unselfconscious acknowledgment of sex as simply part of the pantheon of typical male interests along with sports, culture, and cool office furniture, makes vintage Playboy feel not just outdated, but like a dispatch from another planet — one where men’s desires had not yet become problematized, let alone subject to interrogation and scorn. Its editorial vision, which placed it at the cutting edge of the media landscape in mid-century America, hit differently in a post-Y2K world. 

The perspective shift was perhaps best embodied by the transformation of Playboy’s founder over the decades — from a young visionary thumbing his nose at the censorious prudishness of a post-war US, to a creepy old man whose penchant for women six decades his junior was as unseemly as his habit of sporting silk pajamas as daywear. By the time he suffered a fatal heart attack in 2017 at the age of 91, both Hefner and the brand he’d created had grown from a modest print magazine into a massive, multi-million dollar, bunny-headed hydra encompassing everything from nightclubs to fragrances to broadcast media and beyond. They were also, however, synonymous with a sort of dirty-old-man sensibility which the incoming generation of progressive millennial tastemakers found intolerable, not to mention repulsive.

Perhaps unsurprisingly, Playboy magazine has struggled to stay afloat, let alone relevant, in a landscape reshaped by digital technology and rapidly shifting social mores. Its most recent gambit: a quiet launch on Substack, where a mix of archived, classic Playboy material lives alongside newer commissions from contemporary journalists.

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“Welcome to The Playboy Reader, the latest development in Playboy’s 73-year history as a literary institution. Yes, Playboy has always featured photos of minimally-clothed women—that’s not changing!—but we’ve been known for our writing, too,” reads the inaugural post. 

There was of course a moment when this did change, albeit briefly, a dark night of the soul for Playboy in a world beswarmed by digital porn. In October 2015, the magazine announced that it would no longer publish nude photos; “You’re now one click away from every sex act imaginable for free. And so it’s just passé at this juncture,” explained Scott Flanders, the chief executive, at the time. That decision was reversed two years later, but the identity crisis it represented is ongoing — as is the abandonment of the magazine’s original tagline, “Entertainment for Men”. In 2019, a new editorial staff comprising half a dozen socially conscious millennials — zero of whom were heterosexual men — sat for a New York Times interview about the new “brand vibe” of Playboy: “intimate” but not “explicit”, and “cheeky” but not “cheesy”. The article noted that the company was “working to expand into cannabis, skin care, sex toys and sexual wellness”; the magazine, meanwhile, abandoned its straight-male-skewed content in favor of interviews with politician Pete Buttigieg and MeToo founder Tarana Burke. In 2019, the cover famously featured male actor Ezra Miller wearing lingerie and bunny ears.

You’d be forgiven for wondering exactly who this new Playboy was for, a question evidently overlooked by its creators amid their fervent quest to distance the magazine from its original readers. In addition to now being on Substack, Playboy has a new editor in chief, a new president of media and branding, and a new home in Miami. It also, as far as I can tell, remains more or less completely confused as to its place in the contemporary media landscape, or whether it even has one. Playboy has consciously uncoupled itself from its original vision; it is, explicitly, no longer “entertainment for men”. But negative polarization only goes so far in the attention economy, and for now, Playboy has succeeded largely in intentionally alienating its longtime readership in favor of making content that is attractive to basically nobody.

Some of this, to be sure, is about the new prudishness of the digital native. Gen Z, so awash in ubiquitous online porn and yet so peculiarly sexless in real life, is understandably bewildered by the notion of a magazine that is made more for titillation than masturbation, that invites the specter of sexuality to cavort playfully through its pages but also expects its reader to actually read. 

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But if this represents a fundamental misunderstanding of Playboy‘s literary appeal, it is even more a misapprehension of men and what they want. Pictures of naked women? Yes, of course, but not only this. Even before the advent of Pornhub and the internet it rode in on, the man who preferred his smut unadulterated would naturally decamp from Playboy to baser pastures; there was Hustler, Penthouse, X-rated video cassettes, an entire rack on the newsstand of B-list publications that contained significantly fewer words and a lot more exposed labia than Hefner’s magazine cared to feature. Playboy valued and published quality writing because its readers were, in fact, readers. They were also men who liked women, and liked looking at them, and saw no conflict between these things because, in fact, there was none.

Today, the consensus seems to be that only a vulgarian could be so comfortable with so little separation between sex and the rest of it, that we are better off for having replaced the casual, ambient eros of the mid century with a world in which sex is both optimized and compartmentalized, guarded by formality and confined to a designated time and place. Behind closed doors; behind the paywall; within the safe and transactional confines of a parasocial and paid relationship on OnlyFans. But if this has been an effective means of banishing sex from places it perhaps doesn’t belong — like the office utility closet — it has also squeezed from the discourse a certain joie de vivre, a certain cheeky symbiosis between high culture and animal instinct, a certain winking acknowledgment of love and lust as powerful forces which (as the song says) birds, bees, and even educated fleas are helpless to resist. 

Maybe it’s too late for Playboy, specifically, outdated as it is in the post-MeToo era, and tainted as it is by the distasteful image of Hef tottering around in a silk smoking jacket and captain’s hat like the cadaverous Ghost of Stag Parties Past. But the readers it existed for — the men who contained multitudes enough to enjoy a spectacular piece of writing on one page, and an equally spectacular pair of breasts on the next? I’d like to believe they’re still out there, still waiting to be entertained. They would read it for the articles, whatever it is; perhaps the real question is whether anyone is bold enough to write them.

But Anderson’s personal world is neither crass nor obvious. It’s a hazy, fairytale place, where a small-town Canadian girl could be discovered on the big screen at a ballgame and launched instantly into fame and fortune, despite never having thought of herself as a beauty. The genre of her inner life is romance. “I think of my life not in years, but by who I was in love with at that time,” she writes in her 2023 autobiography (called, romantically, Love, Pamela).

“I call it ‘soft vision’ like how I look to the camera — looking ‘through’ it — even past it — never a direct stare to the lens but a softened focus.” Not base, but beautiful. Pure. Hopeful, even if that hope is more a function of will than a rational response to experience. Her interests are decidedly wholesome: animal rights, veganism (she published a vegan cookbook in 2024). The Anderson we think we know, and the Anderson she knows herself to be, are very different people.

There’s a version of that mismatch in her acting career. Or “acting”, if you want to be unkind, and a lot of people have been. No one took her seriously, apart from herself. In her first film, 1993’s Snapdragon, she plays “a concubine who happens to have a secret twin”. She prepared by studying the Stanislavski Method.

She was nominated for three Golden Raspberries for her starring role in 1996 comic book adaptation Barb Wire: she won “worst newcomer”, but probably more humiliating was being shortlisted for “worst screen couple”, the couple in question being her “impressive enhancements”. It was the Nineties, so nobody thought to call this “body shaming” and in 1999, she had the implants removed.

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Now, though, Anderson has finally made a film that people agree is good. More than that, they agree that she is good in it. The Last Showgirl is directed by Gia Coppola, granddaughter of Francis Ford and niece of Sophia. It’s the story of Shelly, the “last showgirl” of the title, played by Anderson: a 57-year-old veteran performer in a glitzy Las Vegas revue called Le Razzle Dazzle, who is forced to confront her own aging and vulnerability when the show closes down.

Shelly believes that Le Razzle Dazzle belongs to the historic tradition of the chorus line. The world sees it very differently: to Shelly’s adult, estranged daughter, it’s just an embarrassing nudie performance. And when Le Razzle Dazzle closes to be replaced with a “sex circus” (because the world sees Shelly’s show, not as art, but as a dated bit of titillation), and Shelly is forced to audition for other revues, she has to hear what people really think of her.

A dispassionate but not exactly cruel director, played by Jason Schwartzman (another Coppola), lays it out for her: she’s not a good dancer, and even if she ever could have been, it’s too late for her now to acquire the technical skills. She was elevated because she was young and beautiful, and now she isn’t either anymore. In another film, this could be the moment that our heroine turns out an incredible routine and triumphs over ageist, sexist expectations. But The Last Showgirl isn’t that kind of film, and Shelly leaves the stage, defiant but nonetheless rejected.

It’s a sad, brutal scene, made sadder and more brutal by the obvious parallels with Anderson herself — parallels that the actress deliberately draws out. She changed Shelly’s age in the script to match her own, so when she shouts “I’m 57 and I’m still beautiful!” at the Schwartzman character, the words belong equally to the faded showgirl and to the former pinup playing her. And like sweet, dreamy, flawed Shelly, Anderson belongs to a sexual culture that is essentially a relic.

The Playboy centerfolds that made Anderson famous are as much museum pieces now as Shelly’s bejeweled and feathered headpieces — pushed out by the “sex circus” of online pornography and OnlyFans. As for Baywatch, who needs to watch beautiful women running around in red swimming costumes pretending to be lifeguards when you can watch women in nothing at all having unspeakable things done to them on demand?

Like Shelly, Anderson sees the institutions of sexual entertainment that made her as essentially benign: she remembers life at the PlayBoy Mansion as “a beautiful and sensual chaos”, Hugh Hefner himself as “the epitome of chivalry, a true gentleman — elegant, passionate, so charming, and yet with that little-boy giggle”. Recollections vary on this point: Crystal Hefner, a Noughties playmate and Hefner’s third and final wife, remembered the Mansion as leaking and riddled with black mold, Hefner himself as controlling and squalid in her own tell-all book, Only Say Good Things.

This rose-tinted view is not because Anderson has had a fundamentally benign life: she was sexually abused by a female babysitter as a child, and her own father was violent and bullying, once drowning a litter of kittens to punish young Pamela for disobedience. Even gentlemanly Hef ripped her off: Playboy made millions from re-exploiting her image via calendars and videos, none of which was ever shared with her.

And, of course, there was the vast public humiliation of the sex tape, made privately with her then-husband Tommy Lee Jones, stolen from her home and released without her consent. Lawyers acting for the company that commercially released the tape argued that Anderson had forfeited her right to privacy because she’d voluntarily appeared naked in Playboy; Anderson neither sought nor received any money for it.

With all this backstory, a more ruthless Anderson could have easily have reinvented herself with a survivor narrative to suit post-MeToo tastes, much as Crystal Hefner did. (Which is not to say that Crystal Hefner is untrustworthy per se, only that she made her rebrand with cutthroat timing.) But ruthlessness is not an Anderson trait, and many of the decisions she’s made as an adult fit her poorly for the role of victim.

Take the sex tape. As a victim of revenge porn, Anderson is obviously sympathetic — and yet her own romantic choices don’t suggest much solidarity with other women who have suffered like her. Her third husband (and in fact fourth, because she married him twice) was Rick Salomon, the professional poker player and semi-professional sleazeball who distributed a tape of himself having sex with Paris Hilton, against Hilton’s own wishes.

Then there’s the matter of sexual assault. Again, Anderson could leverage compassion here, and deservingly so. But when Julian Assange of Wikileaks was holed up in the Ecuadorian Embassy to avoid allegations of rape in Sweden — allegations described as “credible and reliable” by the Swedish prosecutor — it was to Assange, and not his purported victim, that Anderson gave her support. She became a regular visitor to the embassy; she calls their friendship “invigorating, sexy, and funny”. Assange maintains his innocence and the investigation was dropped in 2019.

Anderson is a “bad victim”, if a victim is supposed to be ideologically coherent and pure. But the truth is that I like her more for these choices, however inexplicable I find them; maybe I like her more because I find them inexplicable. They seem, if nothing else, heartfelt. Still, the same question hangs over Anderson just as it does over Shelly in The Last Showgirl: just how naive is it possible to be?

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Like the character she plays, Anderson has thrown herself relentlessly at situations that, in many ways, repeat the exploitation and injury she has already suffered. The audition scene is exquisitely painful because, although the narrative requires us to root for Shelly, the director is unavoidably correct. Shelly’s artistry is, at best, limited. Her sex appeal was her asset, and now that’s almost spent. And all this is true of Anderson too, which spikes the sadness even higher.

What makes Shelly a great role for Anderson is that, finally, this is a part that captures the impossible tension between how the world sees her and how she sees the world. When a romantic character is plunged into a pornographic medium, the result of that mismatch is tragedy, and both Shelly and Anderson have a tinge of tragedy to them. They are women who have been used and discarded, but who still insist heroically on the beauty of things.

Except, for Anderson, there is a second act. She is not pensionless and penniless like Shelly. She can be reborn as an actress who plays a woman a bit like herself. She can even afford to turn her back on some of the labor of femininity that was her profession: in the past few years, Anderson has given up wearing makeup and having tweakments, even for red carpet appearances. The effect is surprisingly powerful, both for revealing the artificiality of regular beauty, and (this part is something of a flex) for revealing how pretty she is unadorned.

At 57, Anderson can receive the respect she was denied when she was young, gorgeous and despised. The real Shellys — the working class of the adult entertainment industry — are more disposable, and their futures more bleak. Maybe there’s something to be said for holding onto a faith in glamour despite all that.

As far as Hefner was concerned, he was offering women feminism the way it should be. Being a bunny was a way to move beyond prissy morality and claim sexual empowerment. “Women were the major beneficiary of the sexual revolution,” he told Cosmopolitan in 2015. “It permitted them to be natural sexual beings, as men are. That’s where feminism should have been all along.” That was a self-serving definition from a pornographer, but it was one that some women embraced: if feminism was about a woman’s right to choose, they chose to commodify themselves for profit.

But the obituarist was more right about Hefner’s timing than she could have known. Eight days after his death, the same paper published its devastating expose of Harvey Weinstein’s serial sexual assaults against women, and the #MeToo movement quickly assembled in response. You can’t exactly call it luck when a 91-year-old dies, but if Hefner had lasted two weeks longer, the memorials would have been far harsher judgement about his influence on the 20th century.

#MeToo was, broadly, about sexual harassment; but specifically, it was about the fact that sexual harassment could happen even in industries where women’s sexuality was treated as an asset to be exploited, even in circumstances where a woman might cynically be said to have profited from the encounter. Leveraged consent was not consent. A choice made under pressure was no choice at all.

Perhaps Hefner had sensed the coming reckoning. Six months before he died, he summoned Crystal Hefner — his third and last wife, 60 years his junior — to his bedside, and made her promise to “only say good things” when he was gone. Crystal agreed, but the deathbed setting, the frail old man desperately trying to extend his powers beyond mortality? That belongs in a book — and now her promise is the title of Crystal’s memoir, in which she very much does not limit herself to saying only good things.

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Life in the Playboy Mansion in the late Noughties, she writes, was controlling and transactional. A strict 6pm curfew applied to Hefner’s girlfriends; in exchange for performing regimented group sex, they got bed, board and $1,000 cash a week. To her credit, Crystal is frank about the reason she and other women entered into this high-gloss servitude. When she first visited the mansion for a Halloween party in 2008, she was 21, and Playboy promised impossible glamour and riches. “That ornate front door looked like the doorway to success, to a place that could make all of our dreams come true.”

If you became a girlfriend, you might be able to become a playmate, with a centrefold in the magazine. If you became a playmate, you might be able to parlay that into the kind of fame that Pamela Anderson or Anna Nicole Smith had achieved. Implicit was the assumption that the bad parts of these women’s stories — the stolen sex tape that humiliated Anderson, the drug addiction that killed Smith — could be skipped. In the economics of choice feminism, the undesirable costs of sexualisation were outsourced to the sexualised, never accounted for. Hefner’s mini-harem were forever kept in check by the threat — as Crystal puts it — of being replaced “by another woman with blonder hair, better breasts, and a better nose”.

Hefner had always had a type, going back to the very first issue of Playboy in 1954, which flew off the shelves on the basis of a nude Marilyn Monroe pictorial: slim, fair, busty. Anderson fit this mould, and so did Smith. But whereas in his prime Hefner had made some room for variation — he was, along with everything else, a committed anti-segregationist — by the time Crystal was in the picture, that type had calcified entirely. Photos show him flanked by eerily samey women: femaleness as an entirely fungible commodity. Their hair, breasts and noses all converge onto one ideal, which is to say Hefner’s ideal. This was a work of art as well as nature. When Crystal decided to upgrade her appearance, she went to “the plastic surgeon who did all of Hef’s girls”.

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When multiple women “chose” to turn themselves into Hefner’s fantasy, the result was a brutal kind of physical competition, in which the body itself was remodelled to approach an impossible physical standard — and to demonstrate their loyalty to their master, who was not such a fan of “natural sexual beings”. Women could work within the system and even achieve short-term gains, but the toll of being an object was borne by the flesh.

The women of Playboy were rational actors, certainly, but they were acting in a tiny ecosystem governed by the whims of one man. “Nobody likes a prude, Hef would say, and I could make your own choice about whether to stay or go,” writes Crystal. “After I’d been there for a while, it didn’t feel like much of a choice.”

By this time — the late Noughties — Hefner had become a victim of his own prescience: the America of the 21st century was one he had helped to create, which meant his product no longer stood out. In a Playboy world, who needed to buy Playboy? Nudity was readily available online: why pay for softcore pictures when you could get the hardcore stuff for free? It’s symbolic of how exhausted the Playboy concept was that Hefner ended up selling his mansion to a fan from under himself before he died.

All that was left, really, was the brand. And the obvious way to make money from a brand in the 2000s was to turn it into a reality show. The Girls Next Door had been running for three years when Crystal arrived, stepping into the show as Hefner’s girlfriend number one, although not particularly successfully. As she admits in the book, she was “wooden and quiet”, although in her defence, she wasn’t being paid to be compelling. The deal was between the network and Hefner. He got $400,000 an episode, despite barely appearing. The girls — the stars — got nothing. “It didn’t even occur to me that it wasn’t a fair arrangement,” says Crystal. “I just felt lucky to be there.”

This seems like an extraordinarily unworldly thing to believe, but people — women — who felt “lucky just to be there” were foundational to large chunks of the Noughties economy. It was why girls went wild for Girls Gone Wild, even though they received no more than some cheap beads in exchange for flashing their tits. You could take your portion of the sexual revolution, only if you acceded to it happening on men’s terms.

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Hefner was a pioneer here as well: he built his empire directly on profiting from women’s bodies without sharing the rewards. Anderson has said that being a playmate was “empowering”, but not so much in the financial sense. It launched her career, but in her 2023 Netflix documentary she says she didn’t get a cut from any of the calendars or videos that Playboy sold off her back. And those Marilyn nudes in the first issue? Bought from the photographer for $500. Monroe herself got nothing — a fact that was once seen as proof of Hefner’s business acumen.

And yet, if Hefner was the master of timing, his widow’s book comes too late. Crystal’s isn’t the first book not to “say good things” about Hefner. In 2015, Holly McKenzie — the number one girlfriend before Crystal — wrote her own memoir of the “betrayal and abuse” she experienced in the mansion. In 2013, Jennifer Saginor — daughter of one of Hefner’s best friends — published Playground: A Childhood Lost Inside the Playboy Mansion. Since 2022, the documentary series Secrets of Playboy has racked up an exhaustive 20 episodes. At this point in the #MeToo cycle, the victimisation of women like Crystal is well established.

In fact, she’s told the unflattering story of her time in the Playboy Mansion already — in, among other places, an interview with Howard Stern in 2011, when she and Hefner had temporarily broken up. In the book, Crystal refers to that episode regretfully, saying she “let Howard Stern coax me into saying cruel things about Hef” and “felt awful about it after… like I’d lowered myself even further into a pit of shame and regret”. Yet all she did was share the same truths she’s sharing here — describing the same rigid rules and squalid sex — in a now-unfashionable register. In 2011, she was playing the part of the shameless vixen. In 2024, she’s playing the part of the woman-child, “a kid who went trick or treating somewhere and never left”.

The truth, probably, is somewhere in between. Hefner used women, but he was only able to because women like Crystal believed they could use themselves to extract money and power from the Playboy institution. Part of the genius of choice feminism, from the male point of view, is that it makes women complicit in their own exploitation. Crystal never approaches those subtleties: she says she felt trapped, but then can’t fully articulate why, having broken her engagement to Hefner, she returned to become the last Mrs Hefner.

But it’s the subtleties that would make her interesting. I know Hefner was a goat and a shark. I would much rather read an honest account of the political acumen it takes to become the chief girlfriend, and eventually the wife, of a professionally promiscuous and very wealthy man. But in that sense, at least, Crystal chose her moment perfectly: as his widow, she’s probably the only woman to have made more money from her bargain with Hefner than he made from her.

West Elm Caleb reportedly slept with a lot of women via dating apps, and wasn’t very honest with any of them about what he was doing. Then some of his dates compared notes via TikTok and the result caused so much arguing it was even reported in India.

Why all the noise about some two-bit Lothario in a city a long way away? Well, in one sense, this is as old as humans: the ongoing resonance of mythic figures such as Helen of Troy show we’ve been quarrelling about men, women and sex for a very long time.

But the contours of the argument are also uniquely modern. It concerns a dream of hedonistic freedom that blossomed in the mid-20th century, and that Greer herself helped to articulate. And it also captures the way that dream has soured in the hyper-mediated 21st-century world.

In The Female Eunuch, Greer argued that men have, since time immemorial, stuffed women into a domestic role, in which we’re treated variously as drudge and sexual object. In Greer’s inimitably pithy terms: “a receptacle into which he has emptied his sperm, a kind of human spittoon”.

In turn, she thought, women have internalised a stunted image of our own desires. While our bodies are different, supposedly immutable differences in our inner lives are really imposed by stereotype. And this stereotype serves to “castrate” women, replacing a fully engaged and emancipated “female energy” with a weak and artificial “femininity”.

Greer argued that women should abandon this self-imposed prison. Instead, we should pursue “revolution” – meaning the “freedom to be a person, with the dignity, integrity, nobility, passion, pride that constitute personhood”.

Five decades later, how is Greer’s vision working out? Well, the Anglosphere rejection of suburban domesticity and motherhood is now advanced. The average age of marriage has been rising steadily since the Seventies, while the total number of marriages has declined steadily. Over the same period, birth rates in the US and UK have fallen steadily and are currently at their lowest ever level.

“Childbearing was never intended by biology as a compensation for neglecting all other forms of fulfilment and achievement”, Greer argued. And now that women have more choices, claims feminist Jill Filipovic, we’re voting with our feet (or, perhaps, wombs).

So Greer’s vision of swapping compulsory domesticity for greater female choice, self-realisation and empowerment has been realised, at least for some. But how far did she really swim against the tide in setting this out?

When The Female Eunuch rocketed Greer to international fame, the Anglosphere had already seen a decade of “counterculture”, centred on the rejection of tradition and the pursuit of freedom and desire. And one crucial text for this was Jack Kerouac’s On The Road (1957) – a book that, like The Female Eunuch, celebrated the freewheeling pursuit of passion over the humdrum everyday.

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The central character, Dean Moriarty, is a drifter, a slacker and a hedonist. He floats from place to place, leaving a trail of unpaid debts, disappointed friends, damaged cars and chaos in his wake. He’s also a prolific and faithless shagger, taking up with (and sometimes impregnating) lover after lover before abandoning them – in one case with a newborn baby.

In Kerouac’s telling, Moriarty is depicted both as a walking disaster zone but also an ecstatic, spiritual figure. Far from being abusive, his womanising seems animated by an intense desire to drink deeply from the cup of life, love and desire:

He darted the car and looked in every direction for girls. ‘Look at her! […] And dig her!’ yelled Dean, pointing at another woman. ‘Oh, I love, love, love women! I think women are wonderful! I love women!’

Kerouac celebrated Moriarty’s unthinking and often-callous spontaneity as a kind of saintliness. Greer’s innovation was to lay claim, on women’s behalf, to a countercultural movement whose main characters had hitherto been mostly male.

For her vision of revolution also involved women becoming more Dean Moriarty-like. Women, she claimed, “are not by nature monogamous”. Rather, we should be “deliberately promiscuous”, reject domesticity as “an attitude of impotence and hatred masquerading as tranquillity and love” and (again, frequently, like Dean Moriarty) “run away”.

But footloose emancipation on the Greer and Kerouac model has not been cost-free. Greer the libertarian argued that what gets called “rape” is mostly just bad sex, and shouldn’t be severely punished. But the angry and aggrieved women of the #MeToo era seem far from her breezy confidence that bad sex should simply be shrugged off, especially where it feels coercive.

And we’re witnessing a steady re-evaluation of past attitudes to sexual liberation, too. It turned out, in practice, that no sooner was sex liberated from reproduction than it was re-ordered to commerce in enterprises such as the Playboy pornographic empire. Despite Greer’s disapproval of this development, Playboy was for decades a byword for egalitarian, libertine (and commercialised) sexual empowerment. Now a recent documentary has compiled allegations of abuse and even bestiality, by dozens of the Playmates Hugh Hefner brought to live in his mansion. It turns out that the brave new world of free agency and personal responsibility can mesh uncomfortably with real-world imbalances, whether of power, money or beauty.

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By Sarah Ditum

Meanwhile, the female sexual emancipation Greer pursued has delivered a bonanza for every live-in-the-moment modern-day Dean Moriarty with the looks to enjoy it. In the world of online dating, sex is even more abundant than it was for Dean Moriarty: one twentysomething friend tells me that “photogenic” male friends find female attention so abundant that some are “quite sick of the attention”.

But not everyone lucks out: among those neither married or possessing the charms to “game” online dating, sexual access may be difficult to come by. And among these “involuntarily celibate” or “incel” men, this uneven erotic liberation has spurred a boiling rage, much of which is directed against women. Over on the other side, too, it’s the other team’s fault: every woman exploited in a #MeToo situation, or running afoul of some other sexual asymmetry, points the finger at “patriarchy” (ie men) for her distress.

But the common factor in both cases is a culture in hock to the libertarianism of Kerouac and Greer. For while this worldview was lionised as freedom, in practice what it delivered was a kind of marketisation of the heart, that imagines we can love according to principles of rational choice and utility maximisation. Rooted in mid-century “liberation”, this paradigm powers much of the hostility between the sexes today.

When a man claims that we shouldn’t empathise with Hefner’s Bunnies as they were adult women who should have known what they were getting into, that’s not “misogyny”. It’s just what it looks like when you apply the market logic of freedom and personal responsibility to sex.

The same market logic suffuses the manosphere fixation on “sexual market value” – and concludes that “West Elm Caleb did nothing wrong”. For in market terms, we’re all independent, rational adults; why shouldn’t a man treat women as human spittoons, should they make themselves available in this capacity?

On the other side of the ledger, we find the same mindset in the women who share “first date evaluation” spreadsheets with their friends; in the supposedly feminist claim that “sex work is work”; or in the bleak assertion that all men cheat, so you might as well hold out for a rich cheater. Or the claim that men’s loneliness is men’s fault, for male loneliness is caused only by “a surplus of high value women and a surplus of low value men”.

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What did Playboy ever do for women?

By Rowan Pelling

Instead of questioning sexual market liberalism, all we’re offered to make sense of this mess is a schizophrenic “feminism” wholly in thrall to the same fixation on autonomy – but only for women. This worldview celebrates Greer-esque radical autonomy and sexual permissiveness, while dismissing observable normative differences between the sexes as ‘stereotypes’ and blaming any negative side-effects of this approach on patriarchal revanchism.

Beneath this officially sanctioned surface, meanwhile, lurks an increasingly embittered male resentment, that reacts with gleeful schadenfreude whenever a woman acknowledges that there can be tradeoffs between female “empowerment” and motherhood.

Yet neither side is willing to see the field of courtship as anything more than a low-trust, radically individualist, structurally impermanent market – a grim perspective both reinforced and accelerated by the dating apps that now dominate courtship. And under that cloud of suspicion and impermanence, it’s easy to see how the prospect of an 18-year commitment to a dependent child (and hopefully also to his or her other parent) might well seem wildly implausible, or just unattainable.

Where autonomy conquers solidarity, children are psychologically (and, increasingly, literally) inconceivable. But it’s precisely when we get to children that the persistent asymmetry between the sexes becomes most difficult to deny, as poignantly illustrated by the lives of both Greer and Kerouac themselves.

Kerouac is an object-lesson in the wider shock-waves caused when men refuse to move on from sexual hedonism. He married three times, and only grudgingly paid child support for Jan, the daughter he fathered in his eight-month marriage to Joan Haverty after a paternity test. He met his daughter only twice; her life was marked by poverty, trauma, sexual abuse, drug-taking and finally death at 44. Greer, meanwhile, never had children. Her biographer recounts how she struggled and failed to do so, before eventually taking solace in her animals.

Team Kerouac and Team Greer are both really the same camp, then. But depending on your sex, the costs of liberation are inescapably different – and if we just point fingers at the other side’s selfishness, we miss the deeper truth that beneath the pervasive tone of cynicism are real humans of both sexes. And no matter how loudly disappointment curdles to bitterness, nearly all in truth still long for intimacy, companionship and (in most cases) kids.

Such a craving for solidarity is now nigh-on impossible to square with contemporary norms or social infrastructure. Hard as it may be to admit, this is not the exclusive fault of one sex or the other. And yet compassion for the opposite sex’s predicament is ever more difficult to muster.

The truth is, it’s hard to hold a wake for something most people felt died years ago. For me, the magazine was put on the funeral pyre with Hugh Hefner in 2017, sati style. The man and his mag were irrevocably entwined in a way that’s rare in journal-land, where even Anna Wintour is just one in a long line of well-known Vogue editors.

Hefner pretty much invented the concept of a playboy: he lived the lifestyle and then pumped air into its saggy carcass when it was sinking like a punctured Lilo on the Playboy Mansion pool. The death knell was sounded by middle-shelf men’s mags like Maxim and FHM in the late 90s, which saw the beer-loving lad boot the martini-loving playboy off the shelves.

Forty years of doughty campaigning by feminists had finally paid off; the presence of girlie mags on top selfs seemed like an anachronism. The lads’ mags, with their ribald humour and cool female contributors and interviewees, were placed on family-friendly shelves and given a veneer of respectability. But over the next decade, a flesh race started over which publication could showcase the most naked totty. In 2013 the Co-op asked the low-rent Nuts to put its issues in cover-concealing “modesty bags” and a year later it was dead, alongside most of its brethren. I’d like to say this was down to consumer pressure, but it’s equally true the internet with its unimaginable reserves of filth killed the soft-porn mag.

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Let's make sex education sublime

By Rowan Pelling

Yet as epitomised by Playboy, the girlie mag was the embodiment of intelligent sharp-edged masculine glamour — the sort of thing you expected to find on James Hunt’s or Jack Nicholson’s coffee table, beside a white tux. People (mostly men) read it for the car write-ups, interviews and travel as much as the pin-ups, and in 1975 its circulation per monthly copy peaked at 5.6 million.

In the mid-Seventies, the world was still giddy from the sexual revolution and the backlash was yet to properly kick off. Women wrote and featured in Playboy, the quality of writing was good and the nude pictures were often seen as liberating to the post-war generation. The magazine’s presence in a liberal household wasn’t unusual.

My dad bought into the Playboy myth. When my parents took over the tenancy of a country pub in Kent in 1968, my father decided to keep copies of Playboy on the bar counter, alongside Country Life. If you’re blinking in disbelief, cast your mind back to the way packets of peanuts were sold in pubs. They hung in rows on a cardboard backing and as the packs were peeled away a picture of a busty topless model emerged.  My scrupulously upright mother didn’t complain about any of it until she attended a parents’ evening at our local CoE primary school. She lifted the lid of my big brother’s desk and found a naked centrefold inside it  It transpired he’d been charging other boys 5p to take a look. Playboy was quietly banished and replaced by Punch.

Now it’s time to do the same with the print magazine. Although the brand itself is far from dead. Playboy Enterprises still turns over hundreds of millions of dollars — but it makes money from soft porn TV channels and online content and licensing the famous bunny logo to all manner of companies.

When I saw my wider family over Christmas, I was rather startled to see one of my three 17-year-old nieces wearing a hoodie that had a print on the back of a pouting, scarlet-lipped female mouth chewing on a just-extinguished matchstick, with PLAYBOY writ large above the image. There is, it transpires a wide range of Playboy logo-ed garments designed and stocked by fashion company Missguided, which targets young women. When I asked her if she knew what Playboy was actually about, she said, “It’s cool, right?” and her cousins nodded.  She’d never heard of Hefner, nor the magazine and I might as well have been speaking Swahili when I said, “Aren’t you lot supposed to be Fourth Wave Feminists?”

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What sort of sex do women really want?

By Louise Perry

I would, of course, have been a grade-A hypocrite if I’d told my niece she shouldn’t be wearing a top like that. I’ve edited two erotic literary magazines, been a sex columnist for GQ and had a naked shot of me published in a national newspaper. I always swore I wouldn’t be one of those women who went from thoroughly enjoying her sexuality to ticking off other women for doing the same (Germaine Greer flashing her orifices for Suck magazine, then snarking about Suzanne Moore’s “fuck-me shoes” springs to mind).

Above all, I’ve learned you’ve got to view most things pertaining to sex in the context of their times. The later years of Hefner’s saw his epically naff lifestyle veer towards the nasty and cast a shadow on the magazine. He looked more like a tortoise in a smoking jacket than the Casanova of legend, as he filled the Playboy Mansion with disturbingly young lovers, like pneumatic, playmate twins Karissa and Kristina Shannon. Hef offered girls Quaaludes as “thigh openers” and popped Viagra “like Skittles”, a habit that left him almost completely deaf.

According to one former girlfriend, Holly Madison, who wrote a book about her time in the Playboy Mansion, all girls had a 9pm curfew, had to ask permission to go out unaccompanied and had to agree to unprotected group sex with Hefner twice a week. One of Bill Cosby’s victims, the model Chloe Goins, claimed that she was raped at the Playboy Mansion in 2008 when she was 17, after Hefner encouraged her to have drinks with the comedian.

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Why is the Left so hypocritical about sex?

By Sarah Ditum

Needless to say, the Mansion’s scene was favoured by Donald Trump. The President’s long association with Hefner included him featuring on a Playboy cover in 1990, while in 2006 he rewarded a winning team on the Apprentice with a trip to the Mansion, where according to a female contestant he lent over and said to Hef, “It’s hard for me to tell which of these girls are yours, and which are mine.” According to Hefner’s son Cooper his dad didn’t support Trump as a political figure: “We don’t respect the guy.” It makes for an interesting hierarchy of sleaze when the pornographer denounces the politician.

When you think back to Fifties Hefner, there’s total logic to this pecking order. Anyone who espouses the concept of sexual emancipation should find something to admire in Hefner as a frontline warrior of the Sexual Revolution. He said of sex, “We should embrace it, not see it as the enemy. If you don’t encourage healthy sexual expression in public you get unhealthy sexual expression in private.” It’s clear he knew whereof he spoke, describing his conservative, religious parents (originally from Nebraska) as “Puritan Prohibitionists”.

It became Hef’s life’s mission to overturn their values. He studied psychology at the University of Illinois, while also taking courses in creative writing and art and magazine became his calling. In 1953, after a brief stint on Esquire he raised $8,000 thousand dollars and launched Playboy with headline-grabbing photos featuring Marilyn Monroe in her 1949 calendar shoot (years later he would buy the crypt next to hers in LA). That first edition sold 50,000 copies and is now a collector’s item worth thousands.

That same year, 1953, saw the publication of Ian Fleming’s first Bond novel, Casino Royale, alongside the second of Alfred Kinsey’s great tomes on human sexuality Sexual Behaviour in the Human Female — which informed an astonished world that women could be just as libidinous as men and enjoyed orgasms. The forces that shaped the sexual revolution were mounting.

Hefner quickly established a style that was admired across the magazine industry: racy photo-shoots teamed with top-class writing and an influential central interview. For decades literary men would talk glowingly about the Playboy Interview, as if it had never occurred to them the mag was also full of tits‘n’arse.

I worked on GQ in the early 1990s and it struck me the formula was just the same as Playboy’s (which was when Hef’s mag started losing its USP), but with fewer world-famous writers. The roll call of people who wrote for Playboy is astonishing, including Margaret Atwood, Joseph Heller, Anthony Burgess, Roald Dahl and Ursula le Guin, while Normal Mailer was dispatched to write about Muhammad Ali’s Rumble in the Jungle. Interviewees included Mae West, Ayn Rand, Bertrand Russell, Jean Paul Satre, Better Friedan, Al Pacino and, well, absolutely everyone quite frankly. Hefner established a Playboy Philosophy, was a rigorous campaigner for free speech, and espoused liberal causes including the Civil Rights movement, sending black writer Alex Haley to interview Malcolm X and Martin Luther King Jr.

Haley also interviewed George Lincoln Rockwell, founder of the American Nazi Party, a choice that gave Rockwell a fit of nerves, meaning he kept a handgun on the table throughout the conversation. More than that, Hefner was a leading advocate of women’s reproductive rights and a vocal supporter of legalising gay marriage, saying the struggle was “a fight for all our rights. Without it, we will turn back the sexual revolution and return to an earlier, puritanical time.”

Of course none of this white-washes the dark excesses of the Playboy Mansion. I’ve ploughed through a tonne of literature on Hefner and while I’ve never found anything that proves he himself was guilty of what a court would view as sexual assault, it’s clear the money, drugs and lure of fame were a form of coercion to the young and vulnerable. And he presided over a flesh-show that made others feel amoral behaviour was permissible.

Even so, it would be careless to dismiss the contribution Playboy and Hefner made to sexual liberation, the civil rights movement and to the cause of good writing in the mag’s first two decades. One of the curses of getting older is realising how many celebrated historical figures have feet of clay: should I cease to admire all Marie Stope’s efforts to ensure women had contraception and access to abortions because she was, at the same time, a committed eugenicist? So I won’t tell my niece to take off her sweatshirt, but I might buy her Holly Madison’s memoir and a Seventies copy of Playboy, so she knows the dual nature of what she’s buying into. As Hef would agree, informed is empowered.