Surprises keep us going. Writing and filming about self-portraits for the book and television programme of The Face of Britain, I thought I knew all the early ones. And then, in Margate, in a show at the Turner Contemporary of loans from the National Portrait Gallery, I was given a happy surprise. A little thing packing a big punch, the first self-portrait painted in oils in England is not much bigger than your smartphone.

The elderly artist Gerlach Flicke, painting in 1554, probably in the Tower of London, looks sombrely out from his confinement, along with his cell mate, a gentleman pirate glorying in the name Henry Strangwish, also known as Red Rover. Doubtless the modesty of the format was all that could be managed in prison but somehow the confinement of the scale echoes the captivity of its subjects. Flicke has added a trompe-l’oeil vertical bar painted to look like flaking wood, as if separating the two men as well as shutting them off from the world. The image records a particular moment and a universal plight.

Flicke must have been bewildered by his predicament. An immigrant from Osnabrück, perhaps with Holbein connections, he had been rated highly enough to paint Archbishop Thomas Cranmer, the theological major-domo of the Reformation. He had also painted Protestant gentry such as Sir Peter Carew who, on the accession of the Catholic Mary, was involved in a botched rising. Though Catholic himself, Flicke might have been incriminated by association. As for Strangwish, he had a habit of preying on Spanish shipping, tactless given the sympathies of the new queen.

Lux in tenebris. Light in the darkness; freedom in captivity. Somehow the frightened old man in the shadow of the gibbet crafted something poignant and precious. His hand, at any rate, could not have been shaky because the squirrel-hair brush is manipulated with perfect control to describe the colours of the paints on his own palette, the lines of his fingernails and the stops on the head of Strangwish’s lute (for the leonine Red Rover was evidently a musical pirate).

‘Gerlach Flicke; Henry Strangwish’ (1554) by Gerlach Flicke
‘Gerlach Flicke; Henry Strangwish’ (1554) by Gerlach Flicke © National Portrait Gallery

With the same dexterity, Flicke paints inscriptions above each of their heads, written in different tempers and languages. For the pirate, an endearingly ponderous pun. Thus, it says, Strangwish “strangely” depicted is, “garnish’d” for his delight. In the prison slang of the day, “garnishing” meant greasing the palm of the jailer for better treatment, so perhaps Flicke was doing the Rover that favour? But at some point a more sombre mood overtook him. Above his own head, in Latin, he tells us that “this was the face of the painter”, so that he “might be remembered to his friends after his death”, an end he must have assumed would come soon.

In fact, both men survived their incarceration, though each died not long after; the pirate on a French raid, the painter of his years. Just where the picture ended up is hard to say; it is a miracle it survived at all, such a little thing so radiantly charged with compressed desperation expressed in two tones: gallows humour and the wistfulness of mortality. In Margate, with the gunmetal light coming in from the shingled shore, it gripped me in its illumination. I looked and looked.

Which, these days, we seldom do. We are all portraitists, Insta-artists, now. We lift, tap, look down to see what we’ve got, send. The condition of our portrayals is exactly the opposite of what prisoner Flicke assumed: ephemerality rather than the fixing of memory. We concentrate when we look at the screen, not when we survey another’s face. The long gaze, the locking of looks, has surrendered to the fleeting, furtive glance, a retinal tic. We chuck the snap or the selfie into the brimming e-bin of images and immediately its uniqueness is lost in the crowd. In minutes the face, if transmitted on Snapchat, will auto-liquidate.

Portrait of William Shakespeare, associated with John Taylor, oil on canvas, feigned oval, circa 1610
William Shakespeare, associated with John Taylor, oil on canvas, feigned oval, circa 1610 © National Portrait Gallery, London

Snapchat’s founder and chief executive Evan Spiegel, adopting the patient tone of Interpreter to the Oldies, has explained that, nowadays, face-catching is just an extension of casual conversation, akin to an exclamation, like a personalised emoji, assumed to be transient and forgettable. The notion that our identity is the sum of our lived experiences, that our life itself is the company of those with whom we have shared it, Spiegel thinks is quaintly analogue, as is the sentimental assumption that there is some sort of core persona which might be revealed on a countenance. In this contemporary view, there is no singular version of us available for embodiment; only disconnected impressions, all of them elusive and unstable. Snapchat identity is no more than the fleeting moment itself: mercurial, protean, fugitive.

Still, a good many of us cling obstinately to the consolations of persistence: above all, the remembrance of faces and the belief that it is possible, in skilful hands, to capture the essence of a person, alive or dead, on their face, well enough to convey a sense of being in their company. This is especially true when portraits are made from fear of losing a loved one. In May 1633, after the shockingly unexpected death of his wife Venetia, Sir Kenelm Digby, scientist, privateer and courtier, learned that an autopsy had been ordered by the king. Before the surgeon was due, Digby summoned his friend Anthony van Dyck to their house in Charterhouse Yard. Van Dyck painted Venetia as if she were merely asleep, her lips still full and warmly coloured, cheeks as rosy as the petals scattered on the counterpane. For the inconsolable Digby, the picture sustained his desperate wish that, somehow, Venetia lived on. At night he propped the painting on a chair by his bedside from where, in his insomniac distraction, he imagined it spoke to him.

That people still want to be in the company of the depicted; that the bonding of looks somehow makes a personal and familiar connection, is borne out by the crowds thronging the National Portrait Gallery every day. It’s not just the famous, immediately recognisable faces — the Queen, Paul McCartney, Kelly Holmes — before whom the crowds stop and stare. There is a lot of peering and stooping at captions telling the visitor they are looking at the meaty chops of Ben Jonson, or Joshua Reynolds’ sublimely weird portrait of the sublimely weird Laurence Sterne, or the first known portrait of an African in England, Ayuba Suleiman Diallo, a copy of the Koran hanging about his neck. The “National” part is important. With the character of the country now in play — with or without Scotland, in or out of Europe, an Atlantic or a postcolonial identity — it’s not such a bad thing that people spend time in the company of those who, one way or another, have put an imprint on what Britain has come to be.

The historian Thomas Carlyle believed a portrait was “worth half a dozen biographies”. Carlyle became an ardent promoter of the project of a national-historical gallery, along with Viscount Stanhope, its original enthusiast, and Thomas Babington Macaulay, about as politically opposite from Carlyle as could be imagined but united with him in this one enterprise. The time — the mid-1850s — was one of imperial swagger punctuated by attacks of nerves. The Great Exhibition had shown off Britain’s industrial power to the world. Yet somehow this had not translated into victory in the Crimean war and rumblings in India were about to explode into insurrection in 1857. The National Portrait Gallery was meant, first and foremost, as a proclamation of what Britain was through a pantheon of past genius, political, military and literary — all, it goes without saying, male. The very first donation was the “Chandos” portrait of Shakespeare, named after the duke who originally owned the painting, and the best of the original collection was Sir Thomas Lawrence’s masterpiece: the unfinished sketch of William Wilberforce, a figure who, given Carlyle’s ugly racism, he is unlikely to have admired.

Ayuba Suleiman Diallo (Job ben Solomon) by William Hoare, oil on canvas, 1733
Ayuba Suleiman Diallo (Job ben Solomon) by William Hoare, oil on canvas, 1733 © OM.762. Orientalist Museum, Doha

The Face of Britain has, in its three editions — book, television and gallery show — not been conceived in a spirit of defensive reassurance, much less in a futile hunt for some sort of emblematic British look. Nowadays it’s self-evident that we have faces, not a face, and it is exactly their multiplicity, difference, variety (always a feature of British history) which the project celebrates. Charlie Phillips, who came to Britain from Jamaica as a boy in the 1950s, used the Kodak Retinette hocked to his father by a hungover GI to picture life on the streets and in the pubs and shebeens of Notting Hill in the years after the race riots of 1958. Charlie’s images of black and white school kids or pub customers, in each other’s company despite the violent hysteria that ordered them to steer clear of each other, are an everyday redefinition of what it means to be British.

Likewise, William Hogarth would have had no trouble seeing the Singh twins, Amrit and Rabindra, living and working in the Wirral and marrying the formal patterning and jewel-like figure painting of Mughal miniatures to the carnival of contemporary Liverpool, as heirs to his swarming London tableaux. The twins, whose work is as indivisible as their British-Indian cultural personality, light up with indignation when they remember their art school teachers warning them that they had better get with the modernist canon — Picasso and Sons — if they wanted to avoid being ghettoised.

Oliver Cromwell by Samuel Cooper, watercolour on vellum, 1656
Oliver Cromwell by Samuel Cooper, watercolour on vellum, 1656 © National Portrait Gallery, London

Up-yours refusal of prescribed form has been the great strength of British portraiture over the generations. Whether the subject is single or multiple, there has been, over the centuries, an irrepressible resistance to the frozen mask. Early on, of course, royal portraiture, representing the idea of god-like sovereignty, demanded just such icons. But supreme remoteness is what got the Stuarts into trouble with the iconophobic Puritans. The old story of Oliver Cromwell instructing Peter Lely to paint him “warts and all” probably originated with another artist, the gifted miniaturist Samuel Cooper, who in defiance of the rules of classical taste painted not only the battalion of warts camping on the Protector’s face but also piebald patches of scalp exposed beneath his lank comb-over. The assumption, deeply English (at that moment anyway), was that an image of the ruler based on candid naturalism would bind the loyalty of citizens more powerfully than the cosmetic flattery required by the vanity of kings.

But vernacular familiarity, if it’s going to substitute for grandeur, needs a Shakespeare of the canvas. Isaac Fuller, whose larger than life self-portrait is a study in stagey extravagance, attempted to produce a cycle of enormous history paintings for Charles II, narrating the ripping yarn of his escape after the battle of Worcester in 1651, including the famous hiding place in the oak tree. Over-faithful to the popular book version celebrating Charles’s common touch, the result was, depending on your point of view, either clumsily unfortunate (the verdict of nose-holding commentators of the next generation) or an inspired anticipation of modern pop history.

Venetia, Lady Digby, on her Deathbed, By permission of the Trustees of Dulwich Picture Gallery

The native urge to guy the grand (albeit owing something to the Dutch), re-emerged once the expiry of the Licensing Act at the end of the 17th century made prosecutions for libel all but impossible. The momentous result was the distinctively British reinvention of political art as comedy. Satirical prints, cheaply available, even rentable overnight or for the weekend, democratised the ownership of portraiture, as caricatures created a new kind of popular entertainment.

Attack portraits — such as James Gillray’s vicious turning of William Pitt the Younger into a giant toadstool standing on a dungheap — dragged the mighty through the mire of caricature. Reverence replaced by ridicule, the criteria of fitness for portrayal collapsed: if a high-class tart such as Kitty Fisher had the wherewithal to pay for Joshua Reynolds to paint her as Cleopatra, he would do it and do it well. Celebrity criminals? Bring them on. In 1733, William Hogarth went to see the convicted 22-year-old murderess Sarah Malcolm in Newgate a few days before her execution and made a brilliant oil sketch, featuring the brawny arms the public expected, a face as homely as a risen bread loaf but defiantly averted from our gaze as if answerable only to the supreme judge above. Circulated around Britain, a print made after the sketch was an instant sensation.

People love portraits because they are the least self-contained of all the genres of art. Our instinctive sense of being part of the action, part of the reason why they exist at all is not misplaced. And the fact that each and every portrait results from a contest of visions — between our vanity and the artist’s obligation to mess around with it — only makes for added involvement. Very often the backstory behind a portrait’s creation is as engaging as what lies on the canvas itself.

‘Self Portrait’ (1913) by Laura Knight
‘Self Portrait’ (1913) by Laura Knight © National Portrait Gallery

So it is with one of the most stunning masterpieces in the National Portrait Gallery. Laura Knight’s self-portrait with nude model — duplicated on canvas and in life in case we miss the point — was a one-picture revolution in the suffragette year of 1913. Its back story was the confinement of women art students to learning the indispensable discipline of figure drawing from plaster casts rather than the life, a privilege afforded to men. Knight had endured this insulting experience at Nottingham School of Art and almost certainly noticed that modernist painting, in the hands of Courbet, Manet, Sickert, often featured the clothed artist in the presence of his nude model. Knight’s stroke of genius was to take back the female nude and, in so doing, create a kind of working sisterhood, without a trace of pompous sententiousness. The usual ingratiation, heavy with erotic nudging, is missing. Both women are at work, with better things to do than stare at us even as we stare raptly at them. Knight gives us her professional profile, brushes in hand, the brushes which have produced this explosion of colour. And the body of her model, Ella Naper, is beheld from behind. Never mind the angle, the idea — spirited, audacious, radiant, bravely accomplished — is indeed the face of Britain.

‘The Face of Britain’ is published by Viking. A BBC2 series based on the book begins on September 30 and an exhibition runs at the National Portrait Gallery from September 16.

Simon Schama is an FT contributing editor

Slideshow photographs: The Singh Twins

Photographs: National Portrait Gallery

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