What was most striking about the Duke of York’s interview with Emily Maitlis? It was a toss-up: his views on sex (it’s a “positive act” for a man, apparently; and if you can’t remember it, ergo it didn’t happen) set off a logical cascade into the abyss (if, by extension, it’s a negative act for women, does that mean we don’t “decide” to do it? In which case, are we always, basically, waiting for it to be done?). His line about adrenaline – that he overdosed on it during the Falklands war, and can therefore no longer sweat – has triggered a race between medics and picture editors to see who can disprove him fastest. His use of the Pizza Express in Woking as an alibi circa 2001 has generated a lot of mirth (check out online reviews since Sunday night). But surely the slam-dunk astonishment lay in what he didn’t say: that he was sorry for the victims of Jeffrey Epstein; or indeed, that he had given them any thought at all.

“There was always something tragicomic to Prince Andrew’s trajectory,” says Catherine Mayer, the author of Charles: The Heart of a King, and co-founder of the Women’s Equality party. “Or at least it was tragicomic until we found out about his association with Epstein, and then the comedy drained away.” The “playboy prince”, they called him in the 1990s, after his divorce from Sarah Ferguson; before the marriage, pretty much from the age of 18, he was known as Randy Andy, or as the Daily Mail put it, “Randy Andy and His Web of Armcandy”.

Not that the prince would recognise this characterisation. Asked by Maitlis why the public perceived him as “the party prince”, he told her this was “a bit of a stretch. I don’t know why I’ve collected that title because I don’t … I never have really partied.”

With Koo Stark in 1999. Photograph: Alan Davidson/Rex/Shutterstock

In his youth, though, partying was what second sons were expected to do. As Alan Rusbridger put it in 1986, “that is the problem with being the younger brother of the heir to the British throne. The press can, on the whole, think of only one interesting thing about you, and that is who you go out with/are destined to marry.” And it was moderately interesting at the time for its sheer variety, and, in retrospect, for the insight that coverage gives to the way society thought about women, men, relationships, class, hierarchy, the lot. What Rusbridger called his “gallery of crumpet” were always described in terms of hair colour – usually “blond” but occasionally “flame-headed”. There were some weird formulations – “Tracie Lamb, an ex-college girl from Surrey” (you can tell she’s unsuitable, but is it the college or Surrey?), and some much more obvious ones: “model”, “former Miss UK”, “model and actress” …

“He particularly enjoyed the friendships of the model and actress Katie Rabett, the actress Finola Hughes and the model Clare Park because of the different worlds they opened up for him,” intoned the Daily Record, which as late as 1996 was still trying to imbue this coverage with respect, portraying the friendships as some kind of cultural safari for the curious mind. Generally speaking, by the time of his separation in 1992, that kind of sycophancy had ebbed away. As Mayer puts it, “he very quickly went from being a sort of bachelor prince to being somebody who has no use, no purpose, spends money too obviously, takes too many flights, gets his bad nickname, gets married, gets divorced. He went from being the golden prince to being the embarrassing uncle in a series of very inevitable steps. And that was before he became as embarrassing as he is now.”

Even during his heyday, there were multiple tensions to his role, his image and his self-fashioning. To have a shagger in the royal family was hardly a new thing, and the tabloids revelled in the rich history. This is from the Daily Record again: “His great-great-grandfather, Edward VII, for example, was one of the most celebrated playboys in Europe, dedicating his life to horse racing, yachting, carousing and – above all – mistress-bedding”. Prince Andrew’s very existence returned the troubled psyche to simpler times, when mistresses were hunted like stags – and, hey, maybe being bedded was a trace more empowered than being the other kind of royal female, who just gets to dress in a pie-crust collar and produce young.

With Donald Trump and his future wife, Melania, in 2000. Photograph: Davidoff Studios Photography/Getty Images

Yet this was the 80s. So even though Prince Andrew’s relationship with the actor Koo Stark at the start of the decade was mainly a problem for the Queen, according to rumour (of particular concern was the film Cruel Passion, in which Stark’s character gets raped by a peer and two grave diggers, and is savaged by alsatians), there was also an amount of feminist disquiet. I mean, nobody thought that every relationship ought to end in marriage, least of all an 80s feminist. But a relationship with a woman who, never mind a ring on her finger, would probably not be allowed round an aristo dining table … it looks a tiny bit like using her. As an understanding of women as equals gained ground as the normal way to look at the world, Prince Andrew was increasingly marginal to that.

He was redeemed in the mainstream by his stint as a helicopter pilot in the Falklands war, though that generated some stomach-churning brown-nosing: “His arrival on the scene has given a new meaning to the initials HRH. With Andrew, they stand for His Royal Heart-throb,” is a line biographer Andrew Morton must surely have paid for in self-respect. “Warrior prince” came up a lot, too. So for a while, Prince Andrew was just Classic Royal, maybe a wastrel and a gadabout in peacetime, but a standup guy in a war. And then in 1986 he married, and all the Queen’s qualms were soothed. For about one second.

The union with Sarah Ferguson was not an especially happy one – 10 years later, Ferguson joked that she passed the time renting videos while he frolicked with 27 concubines – but rich people’s unhappy marriages aren’t fundamentally more interesting than regular people’s. When they separated in 1992, their problems became more specific: it was the same year as Charles and Diana separated. Because Andrew and Fergie had always seemed like more of a joke couple, a bit more boisterous, a bit less dignified, and because of the lurid infidelities that surrounded the split (obviously, the toe-sucking stands out – if you’re too young to remember all this, I would strongly discourage Googling it), theirs seemed more like a comedy subplot to the main tragedy. Yet both divorces represented quite a serious crisis for the royal family. As Mayer explains: “The monarchy is smoke and mirrors. It exists, and there is a consensus, though a fraying one at this point, because it appears to have a unifying representation of the ideals and values of the nation. So when they started getting divorced, there was a sense that they were reflecting too accurate a portrait of who we really were.”

That is even more of a problem when your job is as amorphous as Prince Andrew’s was by 2001: no longer in the navy, he was a roving trade envoy, spreading the amorphous message that Britain was – God knows, as good as its word? Classy? For sure, his wasn’t a very feelgood life story; but he probably could have weathered these questions of constitutional purpose were he living a life of green wellies and speciality dogs. Instead, he was at the model Heidi Klum’s Halloween party in New York, where the theme was “kinky sex”, according to the Mail. From beaches in Thailand with “bikinied beauties” to “three-day flirtations with a Playboy pinup” in Los Angeles, there was a pictorial record of a man who has “trade ambassador” on his lapel, but doesn’t seem terrifically interested in the steel industry, put it that way. Ghislaine Maxwell was always tacitly blamed for introducing him to the “fast set” (he had met the daughter of the disgraced Robert Maxwell while she was at university); obviously, that was before we started blaming her for his friendship with Epstein.

Prince Andrew during his BBC interview. Photograph: BBC

Perhaps the problem was not so much that his behaviour didn’t befit his office, as that it didn’t befit his years. Really, this was no different from his life in the 80s – it just wore better on a man with a future ahead of him. Yet there was always this catastrophic carelessness, the myopia and indolence of intense privilege commingled with the weird self-pity he seems to have himself brought to the mix. He was known to be not very bright, but there is a distinctive flavour to the stupid things he says. Even without the Maitlis interview. Even if the questions go no deeper, the accusations against the prince himself are never substantiated, and the extent of his knowledge of the crimes of others never proved, Mayer says, “this much we absolutely know: that he stayed with a convicted child sex offender and he gave cover by doing so. This is how it works. These are the circles that close ranks precisely when they should be open.”

In the light of which, all that jollity, all that eye-rolling, all the indulgence of his early public life curdle. It’s such a thin line, isn’t it, between devil-may-care and sociopathy?

• This article was amended on 19 November 2019. An earlier version incorrectly referred to Catherine Mayer as the leader of the Women’s Equality party, when she is its co-founder. The title of a book attributed to her has also been changed.