Hugh Hefner: dirty old man or frontline warrior in the sexual revolution? Credit: Robert Mora/Getty Images

April 17, 2020   6 mins

Hark! Listen to the sound of no one sobbing. Playboy magazine published its last print edition this month and is now retreating online, blaming the pandemic.

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.

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?”

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.

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.

Rowan Pelling is editor of The Amorist and a comment writer for the Daily Telegraph. She edited The Erotic Review magazine for eight years (1996-2004)