Portraits of monarchs matter. They bind together countries, define how eras are remembered. And the likenesses of Queen Elizabeth II are no different – except in their profusion. During her reign as Britain's longest-serving sovereign, the late Queen was the subject of almost 1000 official portraits. With characteristic grace, she was, by all accounts – including that of Platinum Jubilee photographer Ranald Mackechnie – an amiable, chatty and surprisingly fidgety sitter.
Certainly, the roll-call of first-rank names who wanted to depict her, albeit often unofficially, was astonishing: Andy Warhol, Gerhard Richter, Lucian Freud, to mention only three. And thanks to the mass media she became, according to the National Portrait Gallery, probably the most portrayed person in British history. Already in 1947, five years before her accession, the News Chronicle was calling her "unquestionably the most publicised young woman in the world".
Beneath the surface of that fathomless ocean of imagery, in among the rocks of stiff official photographs and the weeds of the paparazzi's long-lens snaps, are the visual pearls by which future generations will remember Elizabeth II. And not only her, as both private individual and public monarch, but also the society over which she held sway for seven extraordinary decades. The deference that defined Britain at the start of the so-called "new Elizabethan Age" has disappeared. In its place, for good or ill, are the more spontaneous and informal, touchy-feely values of the current moment. And this transformation is reflected in the evolution of the Queen's portraits. So, looking back, which among her phalanx of portraitists succeeded, and who failed?
Like, I suspect, millions of others, I will always have the most affection and respect for the late Queen's portraits from the '50s – even though they predate my own birth by decades. This was, if you like, Her late Majesty's peak "iconic" period, when she appeared most glamorous and fairy-tale regal, by turns film star and royal goddess. It was the moment when her image – young, luminous, commanding – crystallised in the mind's eye of her subjects.
Is it any surprise that, following the announcement of her death, Cecil Beaton's splendid, imperial Coronation portrait, as glittering and pristine as a snowflake, was so widely reproduced? Taken inside Buckingham Palace, it set the bar high for every portraitist who followed, and still provides the classic example of the genre going, as it were, "all out". Against an imposing (and self-consciously artificial) backdrop reproducing the interior of the Henry VII Lady Chapel at Westminster Abbey, the 27-year-old Queen is seen in full regalia, wearing the Imperial State Crown and a special gown designed by Norman Hartnell.
From the same period, society photographer Dorothy Wilding's smart, svelte black-and-white official portraits, 24 of which are currently on display at Buckingham Palace, present a chic young woman with a subtle sensuality (the antithesis of Freud's gangster-land matron, painted half a century later). These portraits were the basis for Elizabeth II's image on coinage and bank-notes, as well as millions of postage stamps issued between 1953 and 1971. Yet the former Wedgwood designer Arnold Machin's profile bust, sculpted in low relief during the mid-1960s, became even more famous: with Her late Majesty's blessing, it superseded the Wilding series, and is still reproduced on Britain's stamps today. It may, in that sense, be the most reproduced work of art in history.
Another formal portrait that achieved longevity – albeit, in part, because of its manipulation by others – was Peter Grugeon's Silver Jubilee photograph of 1977. It became the source for both Jamie Reid's design for the sleeve of the Sex Pistols record God Save the Queen, in which the late monarch's eyes and mouth are irreverently overlaid with cut-up newsprint in the manner of an anonymous ransom note, and Warhol's 1985 series of candy-coloured silkscreen prints. The four images of the latter are pretty, rejuvenating Grugeon's original by removing a few lines and wrinkles in the manner of an artistic face-lift, but – forming part of a wider portfolio titled Reigning Queens – they tell us most about the artist's fawning fascination with skin-deep celebrity.
But it is Pietro Annigoni's oil painting of 1954–5 – which I recall, as a boy, finding overwhelming – that still, for me, represents the apogee of Elizabeth II's portraiture. Commissioned by the Fishmongers' Company, it got off to a rocky start. Initially daunted by his Royal sitter, the Italian artist was uncertain how to proceed, until, as he worked on a sketch during one of their 15 sittings, she observed: "When I was a little child, it always delighted me to look out of the window and see the people and traffic going by."
The image clicked into place. Wearing the navy velvet robes of the Order of the Garter, the late Queen becomes an elegant colossus, surveying a wintry landscape reminiscent of a scene by Pieter Bruegel the Elder. Those icy fields, however, serve to offset the warmth of her exquisite face, so that, although she is evidently pensive, brooding on her burdensome responsibilities, she is still relatable and vigilant, not remote. In 2007, Annie Leibovitz, the American portrait photographer, alluded explicitly to the painting, underlining its enduring power. (Unfortunately, Annigoni's second portrait of Elizabeth II, from 1969, which repeated the formula of her standing alone against the sky, turned her into little better than a mannequin.)
Many brilliant and memorable portraits of the late Queen have appeared since Annigoni's naturalistic earlier achievement. For instance, Richter's crepuscular, monochromatic lithograph of 1966, in which Her late Majesty's face, based on a newspaper photograph and seen in close-up, is dramatically blurred, offering the last word on the mysterious, enigmatic aura of monarchy; or Chris Levine's Lightness of Being (2007), which came about by accident, as Elizabeth II shut her eyes in between eight-second camera takes as the artist endeavoured to capture sufficient data to create her first holographic portrait. The latter emphasises her role as a spiritual leader: part benevolent White Queen, part Defender of the Faith, irradiated by an eerie, possibly divine glow, which reinforces the sense of inner enlightenment indicated by her shuttered eyelids.
As for the duds, Justin Mortimer's likeness, from 1998, is perhaps the most spectacular. In it, the late Queen, wearing white gloves and a green frock, is dwarfed by a vast and vapid matt-yellow background. Most peculiarly, though, her face – one eye milky; the other swivelling unnaturally to her left – is disembodied, floating like a shrivelled party balloon against that sunflower-coloured void. Pictorially decapitating your monarch, especially when she sits for you, is surely an unwise artistic move.
And then there's the most controversial of the lot: Freud's downbeat, decidedly unflattering portrait. Think heavy jawline, five-o'clock shadow. Unveiled in 2001, after the artist had laboured over it for 18 months during sessions at St James's Palace, it could be accused of many things, but never buttering up. I still don't quite know what to make of this forceful, yet at just 9 inches high, tiny image, the surprising dimensions of which tell you all you need to know about Freud's cussedness. According to its defenders, it expressively articulates the careworn soul of the nation's matriarch. I find that hard to swallow, but will approach this postcard-sized painting without prejudice when it appears in the National Gallery's Freud retrospective next month.
If nothing else, Freud's portrait reminds us of the conundrum faced by every artist tasked with depicting Elizabeth II: how to suggest something of Her late Majesty's internal life when her public persona was defined by the unknowability of her thoughts. It's no doddle to animate the mask of a sphinx.
When Royal portraiture works, though, it is singularly persuasive. At primary school, like many others, I was transfixed by those sparkling portraits of our Tudor and Stuart kings and queens: Holbein's overpowering images of Henry VIII; Elizabeth I's Darnley and Armada portraits. These were originally propaganda, of course, but so effective: icons of God-given authority, which, as a boy, I endlessly and lovingly copied. This week, I bet, schoolchildren up and down the land will be doing something similar with their favourite portrait of Elizabeth II.