AS the disco lights flash around the death of Hugh Hefner, founder of Playboy and all its mildly stained works, I have two stories about my tangential encounters with the soft-porn empire (other than some fumbly teenage memories). Granted, they may reveal as much about me as about the phenomenon itself.

The first is an admittedly terrible recollection. It’s 1989, and my brother and I are on a music-promotional tour of Germany. It’s not going well, and we irascibly rumble toward the final appointment of the day.

In the foyer of the building, one wall is entirely covered with a giant picture of a fully occupied stars and stripes bikini. It turns out we’re in the offices of German Playboy (though we’re speaking to another magazine, not them). The lead singer goes radio rental, and in the resultant stramash a make-up mirror is dramatically shattered to pieces. Not a cherished memory, on every level.

The second story is funnier. In 1995, I was working for BBC Radio Scotland in New York, doing a show on African-American popular culture. One of the contributors was Nelson George, the brilliant music critic. In the spirit of due diligence, I went off to find out where he was currently writing. At that time, he was the music critic for ... Playboy.

The internet being a sputtering affair in the mid 90s, I gingerly went up to the front desk of the New York Public Library and asked for “the last six months of Playboy, please”. With much peering over half-rimmed glasses, the copies were ceremoniously brought to me.

I carefully found Mr Nelson in the index, opened to precisely the right page, carefully carried the magazines to the relevant photocopier. After a sweat-bathed 15 minutes, I got out of there as quick as my Doc Martens could take me.

Both these tales suggest that farce and embarrassment is as much the inheritance of Hugh Hefner’s empire as commercial success and cultural change. But as an advocate of the power and potential of play, I want to push back on the definition of the term that’s implied by Hefner and his enterprises.

In the last few days’ coverage, we’ve been regaled with the media images that define Hefner in his last few decades. He’s wearing black silk pyjamas and a red silk dressing gown, champagne glass in hand. There’s a Bunnygirl on either arm, as he stands in front of his kitsch-tastic LA mansion. It is assumed he is on his way to the “Grotto”, the pleasure-cave that sits beneath his gravelled driveway.

Now, to be pernickety, what this really projects is a “leisure boy” rather than a Playboy. That is, Hefner’s life is one where a male’s reward from his alienated labours isn’t some diversion at the weekend, but a permanent 24/7 condition.

Mix that with an ambient sexism, and things go horribly, seedily wrong. In these last few days, we have been reading the details of Hefner’s various harems – the Bunnies who chose to live with him, under vaguely defined contractual conditions.

These women perform nearly all the leisure services that a WorkBoy could dream of: entertaining conversation, public adornment, group lesbian flirtation and dutiful, Viagra-enabled grinding in the bedroom.

Nancy Jo Sales’ Vanity Fair article from 2011, where she hung out with Hefner and his entourage in Los Angeles, is a downbeat and devastating account of the eventual tedium of the sybarite’s lifestyle. Most striking is the ill-concealed cynicism of the resident Bunnies, glumly hoping that services rendered will bring them their centrefold moment.

So far, so naff, maybe even nasty. But there’s a wee bit more to the Hefner story than this.

Take the term “playboy” (or even “playgirl”) itself. In 2017, there is the possibility of these terms being entirely reframed. If play is, for adult humans at least, about openness, flexibility and boundary crossing, then aren’t the true “play-people” of the current moment those who are actively embracing gender fluidity?

What’s interesting is that Hefner’s history opens up to some of this fluidity. In a 1999 Washington Post interview, Hefner openly admitted a period of bisexuality, at the very height of his swinging in the 80s: “I was testing the boundaries, just knocking down walls.”

On YouTube, you can find Hefner’s 1969 live show Playboy After Dark. In the first item, he points out the compromises made in the film version of Gore Vidal’s Myra Breckinridge – where Myra’s actual sex change is fudged in the movie as a bad nightmare. Hefner was a stalwart campaigner for same sex marriage, LGBTI rights in general and support for abortion laws.

All of this sits easily within the 60s cliche of “sexual liberation” – the idea that the erotic desire of all for all could melt down convention, unbind the constraints of our identities.

Yet this flatly contradicts the prime symbol of Hefner’s legacy: those buxom Bunnies in their corsets, bowties, droopy ears and fluffy tales, pertly attending to power-suited men reclining in smoky clubs. Rather than free-wheeling desire, this is desire running down tediously predictable channels. Or did the Hef protest his heterosexuality too much, as Shakespeare might have put it?

There is a final push-back against the charge that Hefner’s legacy is just a quixotic muddle of priapism, liberalism, sexism and brand management. And it’s probably the one closest to my own definition of play, which goes back to the etymological root of the word – “dlegh”, from the Indo-European, meaning “to engage”.

Hefner, in that sense, was an authentic player, and really did engage. For example, the literary and public-intellectual ambitions of the Playboy magazine can’t be denied.

Their fiction roll call through the 70s and 80s is ridiculous: Saul Bellow, Margaret Atwood, John Updike, John Cheever, Doris Lessing, Joyce Carol Oates, Vladimir Nabokov, Michael Crichton, John le Carré, Arthur Koestler, Isaac Bashevis Singer, Bernard Malamud, John Irving, Anne Sexton, Nadine Gordimer, Kurt Vonnegut, Yevgeny Yevtushenko. Their interviews with Malcolm X and Martin Luther King, Timothy Leary and Marshall McLuhan, Steve Jobs and (notoriously) Donald Trump were conducted with an eye to shaping public debate.

In a sense, this is Playboy acknowledging the existence of Workboy. It’s good to be informed enough about world affairs to have those crucial watercooler conversations, advancing you a little higher up the organisational ladder. And if you said you read it in Playboy magazine, well then, another path to male solidarity may open up ...

Playboy constantly reminds me of one of the great contradictions about play, as it occurs in the human condition. Which is that it starts out as the birthright of children of both sexes, yet often ends up as mostly a male prerogative.

The “player”, as it comes to us in everyday current usage, is usually used in a neutral sporting context. But “players” are also often defined as financial speculators, or brash entrepreneurs, or sexual strategists – and as it turns out, it’s mostly males you find behind these declared roles.

Again, 2017 might be ringing changes on this. One of the contemporary responses to the Hefner legacy might be to invoke the “player-girl” (let alone woman). I read a major business feature the other day on Rhianna.

It chimed with nearly every feature of male “playerdom” – celebrating her music and media creativity, her entrepreneurial and financial acumen, and her sexual power (Beyonce, of course, registers on all the same levels).

Yet both Rhianna and Beyonce consciously admit their own vulnerability and fragility, as part of their cultural messaging (Bey’s Lemonade project is powerful here). In retrospect, the fragility of Hefner’s world of boys’ play is all too obvious. It’s the desperate, defensive puffing of his pipe in the earliest clips of Hefner’s TV shows in the 50s that is, to me, the biggest tell.

Traditional masculinity is hard work – and increasingly, for many men in the 2010s, just too much hard work. What a paradox for a departing playboy.