He effuses to me about her green eyes and "heart-shaped face" – an odd, adult phrase that he must have overheard somewhere. This moment sticks in my head because it is the first time I have heard a peer of mine express active desire for a grown-up, post-pubescent person. This represents a major step on from my current understanding of human sexual behaviour, which consists of the expectation that intermittently in life, if I am fortunate, a person I don't know will send an emissary across the playground to propose a liaison between us, which will then endure without the complication of direct contact, until one of us sees fit to call it off, by proxy of course.
Well, farewell to those innocent days. Seems now we're fancying grown-ups. Madonna, at this moment, looks like puberty to me. She is perspiration. She is body hair (and BIG eyebrows). She is puppy fat. She is unsettling mood changes in previously mild and trustworthy boys. Even her madcap clothing style – that profligate piling of frills, scarves, ribbons and studs – seems rather to prefigure just how complicated things get once you grow up and no-one lays your clothes out for you on a chair overnight.
Around the same time, in response to the troubling dual stimuli of the annual school nativity play and Madonna's biggest hit to date, I ask my father what the word "virgin" means. Upon unpicking, to the best of my limited understanding, his euphemistic answer, I go into a minor state of shock. As children – and pre-internet children, at that – we perpetually seek out innuendo, inappropriateness, whiffs of sex. We shriek with aghast joy if someone says something that sounds vaguely reminiscent of something that rhymes with something we vaguely think might have something to do with sex. And here's this woman just laying it all out there. Using unambiguous terminology. She's making it too easy. It's confusing. Like we've been trying to steal a biscuit and have been suddenly handed the entire packet. Already opened.
A bit later – 1986. Madonna is married to Sean Penn, but I don't really know who Sean Penn is, except that he is married to Madonna. He has not yet acquired the lofty gravitas that will inexplicably attach itself to him in later years; he is still pretty much just some daft actor who smashes up hotel rooms. Madonna is promoting her True Blue album, by being on television relentlessly, always, it seems to me, with different hair than the time before. The mystique of fame, wealth and power crystallises for me in the matter of Madonna's hair. It is a big thing among girls at school, what your hair is like. Everyone is always growing things out or getting things cut in or getting perms, and larding the resulting arrangements with mysterious and noxious styling products. Harsh judgment attends an unflattering choice.
Madonna's apparent ability to master time when it comes to her hair – to have a crop one minute, like in the Papa Don't Preach video, and a flowing 1940s 'do the next, like in the Live To Tell video – draws my envious regard. It seems really to be the major difference between my life and hers: that she can change the length of her hair dramatically at will. Clearly I have stuff to learn regarding a) the time gaps between video shoots, record releases and TV appearances; and b) the use of wigs. My sister owns a tape of True Blue and I am obsessed with it, but in an embarrassed way, because my father disapproves. There is a General Election campaign going on, and my father is certain that either Madonna is in the pay of Mrs Thatcher's Conservative Party, or Mrs Thatcher's Conservative Party has instigated covert bulk-buying of Madonna's album. It is, he says, too much of a coincidence for an album called True Blue, with bright blue cover art, to be number one and blanket-advertised in the run-up to a closely-fought election. This is my first exposure to a political conspiracy theory.
I will come to share my father's suspicions regarding just where it is that Madonna is coming from. Sometimes she will appear to be well-read, sensitive and politically progressive in ways of which I, as I morph into a sanctimonious lefty teen with slogan badges on my army jacket and a Michelle Shocked album in my Sony Walkman, approve. Other times, especially as the 1990s wear on, she seems trashy, inconsistent and shallow. Here, as everywhere with Madonna, the logic of the striptease applies. She offers a glimpse of intellect, then covers it with a tassle so you're not even sure if you saw it in the first place. She imparts what appears to be a confidence, then contradicts it, mocks you for believing it, or savages you for invading her privacy.
Like A Prayer was described on its 1989 release as radically personal, a confessional of an album; yet its lyrics tell a story far too variable to be revealing – emotional prompts everywhere, but few facts one can confidently pin to the artist. In Keep It Together, her "family is gold"; in Oh Father, it's the site of abject trauma and neglect. The assertive lady of Express Yourself is suddenly prepared to "go for second best, baby" when it comes to the abusive partner in Till Death Do Us Part; and in Spanish Eyes, well, her significant other appears to be fighting in the Spanish Civil War.
She's being a magician: letting us think she's showing her hand without ever doing so. The film In Bed With Madonna extends this pseudo-intimacy with her audience. Far from peeping behind her celebrity mask, it rather welds it into place, showing her as an invulnerable narcissist whose emotions are just fuel for her act. And though the notorious, pretentious SEX book exposes her body, it still feels as cold as its steely covers: she's not laying her sexuality bare so much as playing the part of someone who's laying her sexuality bare.
For a certain period (which will become easy to forget about, after multiple credible comebacks), Madonna is not cool at all. Irony has not yet asserted itself as the dominant note in the cultural discourse, and a serious interest in music is generally seen to preclude any love for pop culture. I have a cassette copy of the Erotica album, but it is hidden behind something worthy and sincere. A certain weariness comes to attend Madonna's one-woman clamour for attention, and playing a right-wing dictatoress in an Andrew Lloyd Webber opera doesn't help her to appear streetwise.
There's a point at which few would predict continued success for Madonna post-millennium; she's a bit of a laughing stock. Yet the Noughties see her reassert herself as the world's most written-about celebrity; and if most of that chatter concerns her relationships, children and appearance rather than the nuances of her art, she still regains her dance floor and critical credibility, aided by a culture moved to nostalgically embrace its battle-scarred pop icons.
What we have faced in this woman is nothing less than the cockroach of pop culture sensibilities: a fame and a creativity so resilient and so cynically adaptable that it may be indestructible. And for all the critiques that have accused her of excessive candour, surely what arms Madonna to keep right on reinventing and surviving is the very fact that she exposes nothing real about herself at all. Her emotional investment in each look, each musical style and each persona is slight, and can be shed without regret once its usefulness is done; her 'emotional' songs are fictional melodramas in the tradition of the Ronettes, rather than outpourings of her soul.
Allied to that absence of true emotional exposure is the fact that, unlike a Judy or an Amy or a Janis or a Courtney, she has never given us the satisfaction of seeing her downed by substance dependence. Once again, this brings to bear a certain suspicion: Madonna is by now the celebrity world's equivalent of the smug sober person. But by her sheer longevity, she's ensured that even those of us who were never proper fans – not really, not after True Blue, not after Hanky Panky, not after the Guy Ritchie era and Swept Away and the whole apparently irony-free embrace of boorish green-wellied English toffery, not after Filth and Wisdom and even more not after W.E. – even we have kept watching, and listening, and responding, for longer than we ever thought we would.
Madonna plays Murrayfield Stadium, Edinburgh on July 21.
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