Here’s a small thought experiment. If time travel were possible, how many of us could be transported back 500 years – to the time of Henry VIII, say – and make a living? How many of us have a modern-day job even vaguely similar to anything anyone might have done, circa 1524, to keep gruel on the table and the wolf (or, more likely, the flea-ridden, bubonic plague-bearing rat) from the door? I can think of only one person: Ralph Heimans.

Heimans is a portrait painter. In 2012, he painted the then British monarch, Elizabeth II. Half a millennium ago, exactly this job – high-pressured, on a tight deadline, surrounded by arcane royal protocol – was performed by one of the greatest portrait painters in history, Hans Holbein the Younger, who painted Henry VIII in London’s The Whitehall Mural (destroyed by fire in 1698). Both men got the gig via important patrons, who manoeuvred them close to the throne (Heimans by the former justice of the High Court of Australia, Michael Kirby; Holbein by the then chancellor of the exchequer, Thomas Cromwell.) Both got only limited time with their royal sitters (Heimans just a single hour; Holbein probably not much more). Both artists made preliminary sketches before producing immense final works (Heimans’ 250 by 342 centimetres; Holbein’s just 20 centimetres larger) using identical materials: brushes of animal hair like sable, paints hand-made by grinding oxides and semi-precious stones into oils like linseed and walnut. Heimans learnt how to make these pigments from an old Polish painter in the 1990s – Holbein from his father in the early 1500s.

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There are, of course, differences between the two men. Heimans generally works on linen, Holbein on wood panel; Heimans uses a camera as an aide memoire, then makes chalk and charcoal drawings once he understands a sitter’s face; Holbein worked up a sitter’s expression from his chalk drawings and then, often, traced it directly onto the final painting. Holbein, in addition, has been internationally famous for centuries; Heimans is little known outside the lofty world of those who can afford to commission his works, which can cost up to $500,000 a pop. (Next month the National Portrait Gallery in Canberra will open a retrospective of his work, entitled Portraiture. Power. Influence., which may well raise his recognition factor – and his price tag.)

But without doubt, both men could enter a time machine, and emerge – shot forward or spun backwards through the centuries – with their rarefied, almost otherworldly career skills entirely intact. And this is because, as Henry VIII’s ambassador John Hutton put it of Holbein, both are men “very excellent in taking of physionamies”.

“No country is more passionate about portraiture than Australia,” says art critic John McDonald. “I think we’ve got more portrait prizes than any other country in the world.” Quite why we love it is less clear, even to McDonald.

“Perhaps because portraits tend to be understandable, approachable,” he suggests: “Far more than those works based on identity politics that dominate museums today. And with someone like Ralph – he’s not exactly the toast of the avant-garde – but he is very, very accomplished, and that level of technical skill is always appealing. The man on the street likes to see something he cannot do.”

“This exhibition has been in development for over four years,” explains National Portrait Gallery director Bree Pickering, who calls Heimans’ works sought-after and “highly representational”. But to paint people for a living, however accurately, is to make a career out of paradox. On the one hand you have your audience, who are in search of a truth, preferably one they’ve never seen before: a rich man’s fear; a queen’s loneliness. On the other hand, you have your sitter, who may want to show the audience many things – their power, their gorgeousness, their humanity – but rarely their truth. If the portrait painter wants to be memorable, he must satisfy the former desire; if he wants to be employable, the latter.

“I have to inhabit the ambiguity between the two,” says Heimans equably, sitting in his studio in Bondi – a simple, high-ceilinged room at the end of a green-leaved garden, with a Star Trek-style airlock double door to prevent Sydney mosquitos from sticking to his canvases. Heimans seems like a very equable guy: 54, curly-haired and quietly spoken, with an air of unobtrusive sympathy. Behind him is an enormous, half-finished portrait of actor Ben Kingsley, who looks neither unobtrusive nor sympathetic.

“As a portrait painter, I have to be attentive to that self-image, that facade, and then come up with my own vision. But the facade is important. Why does a person have it? Is there a particular vulnerability?”

“I want people to get lost in their thoughts.”

Ralph Heimans

He turns towards the canvas of Kingsley, who was knighted in 2001. “So Sir Ben is an actor, and an icon – and it’s quite hard to get him to not be that icon for the world.” He pauses and we both look at Sir Ben, who looks back at us, about to make a point. “That’s why I often encourage silence in the sitting. I want people to get lost in their thoughts.” He smiles. “If you leave someone in silence for long enough, they forget you’re there. Then they’ll either fall asleep, or they’ll begin to dream. And that’s what I’m interested in. That unguarded moment, when you can show something different – something truthful – to the viewer. That’s the whole point, for me.”

Can you always see such a moment? The moment when the public face falls away?

“Absolutely. Absolutely.”

Heimans grew up in Sydney, a product of Australian carefree sun-bleached suburbia. Or not. His father Frank, a documentary filmmaker, arrived in Australia in 1955 as a 12-year-old, having been born to Jewish parents in the Netherlands while they were in hiding from the Nazis in 1943. “A couple – a brother, who was a cabinetmaker, and his sister, both Catholic – took my grandparents in,” explains Heimans. “They hid them in their attic. My father was born in hiding in that attic. He wasn’t allowed to make a sound for the first two-and-a-half years of his life.”

Heimans, his older sister and his younger brother grew up in a house filled with the beautiful wooden furniture made by this man, and Heimans still wonders what impact such a backstory had on his own life. “But it played a huge role, no doubt.”

“Ralph’s distinguishing feature as a kid was his complete lack of interest in the 20th century,” recalls his brother Jeremy Heimans, a social entrepreneur who co-founded activist group GetUp. “He was like a Renaissance-era artist and thinker, trapped in the body of an Australian child, of immigrants, in 1970s Cremorne.” He listened to Beethoven, he read Russian literature, he painted in oils. At 17, he won the now-defunct National Art Award for secondary students. His winning portrait – a winged couple, more Raphael than Chagall, one would guess – was stolen, perhaps by one of the exhibition’s security guards. Heimans knows this because years later, the guard rang him up and tried to sell it back to him. Heimans, laughing, admits he refused to pay, but it says something: a security guard, looking at a picture by a teenager and thinking ‘This will be worth something one day.’ Or perhaps simply, ‘I love this, I must have it.’ Or perhaps both.

These days, Heimans has agents in London and Australia, who field requests and organise commissions; he works on perhaps four paintings a year, which, for private clients, range in price up to $500,000. This is clearly an enormous sum, but as his Australian agent, Philip Bacon, points out, “People who want that quality of work seek him out all over the world.”

Works for public collections, like his portraits of Quentin Bryce or Kevin Rudd, earn far less – about $40,000 each – but come with the satisfactions (and challenges) of a wider audience. “I had successfully resisted having my portrait painted for the Parliament House collection for the better part of a decade,” says Kevin Rudd, former prime minister and current ambassador to the US. “Thérèse, who knows a lot about painting, finally convinced me to talk to Ralph. [He impressed me] with the gentleness of his soul, [and] his genuine interest in the thoughts and feelings of his subject.”

Heimans painted Rudd in his home on the Sunshine Coast, but he often travels internationally for work; when he painted Princess (now Queen) Mary of Denmark – his first royal portrait, and hers, back in 2006 – he was put up in a room in the royal Frederiksborg castle, with a tiny, centuries-old bed and a moat visible beyond the stone window. He might travel to one client’s ski lodge in Switzerland; to another’s castle in England; another’s home in France.

“Ralph’s distinguishing feature as a kid was his complete lack of interest in the 20th century.”

Jeremy Heimans, his brother

All of which is to say, he now moves in a world of calm ease and privilege unknown to most of us. “But I think sometimes people think he lives in that world,” points out his wife Tami Bokey: “and he doesn’t! His works seem so serene – but his own life is chaotic! He’ll have a deadline that cannot shift because there’s an unveiling that someone important [like, say, the Queen] is coming to; he’ll have a backlog of work, and meetings about new paintings, and sittings, and he’ll be starting a painting all over again because it’s two inches too far to the right on the canvas.” She laughs. “I’ll be like, ‘Oh my god, you’re starting again?!’ But he’s unforgiving of himself; he makes this incredible effort with every single piece. He works to the point of utter exhaustion. I’ll find him asleep on the floor of the studio, or he’ll have taken himself off for an MRI because he’s feeling faint, and he thinks he has a brain tumour! I’ll be like, ‘No, you just haven’t slept for three weeks!’ ”

At 18, Heimans used the $2500 he had won for the National Art Award to set off for Europe. “I was absolutely dedicated to becoming an artist,” he recalls, “and there was a whole range of skills I needed, which I thought I’d learn overseas. But I just could not find anywhere teaching traditional techniques.”

The great art schools of Europe, he discovered, were in the grip of a new philosophy. “I remember going to the Royal Academy in London, and they told me they rarely used the life drawing room, and there was no painting instruction!” Heimans is not a man who looks judgmental, but if he were, he would look judgmental now. “It was all about self-expression!”

Returning to Australia, he enrolled in art history and pure maths at the University of Sydney, and drawing classes at Julian Ashton Art School. He did so well at maths – chaos theory – that they asked him to stay on to do a master’s. “I’d moved to Paris by then – I lived there 11 years before moving to London – and it was a kind of sliding-doors moment. But the truth was I was never going to be a mathematician.”

What he was going to be, in fact, was a Venetian painter of the 16th century. Here in Bondi (he, Bokey, and their two daughters moved back to Australia during COVID), Ben Kingsley’s vivid face emerges from a warm red haze like a man out of a dust storm. This haze is the red imprimatura, or base layer, that forms part of the classical Renaissance technique of artists like Titian and Tintoretto.

Heimans, obviously, did eventually find someone to teach him traditional skills: a mercurial Polish refugee he met as a student. “I mean, some of what he’d tell me was …” Heimans pauses. “He’d say, ‘This is a secret Rubens would teach people, but you’re not ready for this secret, so we’ll start with a smaller secret.’ ” He slightly rolls his eyes, grinning. “Or he’d tell me to prime my canvases with gelatin and honey, then they’d all get eaten by ants. But it was very much a master-pupil relationship, and it was a beautiful way to learn.”

As well as practical and technical skills, Heimans has always been preoccupied by verisimilitude. He’s not a photorealist, but the best of his works are extraordinarily lifelike. In a wonderful 2017 portrait of Prince Philip, Heimans has him leaning forward, with what one critic called a menacing smile on his face, looking real enough to bite. “For me, the believability of a painting is very important,” explains Heimans. “If it doesn’t look like the subject, that becomes a barrier to the viewer. And I want the viewer to be fully immersed in the work.”

This quality has led to criticism. In our age of the endless – and endlessly perfectible – electronic image, realistic portraiture is seen by some as at best redundant, and at worst a mere cipher for photography. But Heimans “never copies a photograph – never. But if you know how to read them, photos can help you understand the anatomy of that face: how the light falls across the bridge of a nose; how the bones sit.” Heimans can then draw that face at any angle, from any perspective.

Using this technical skill, as well as his characteristic architectural detailing, rich colour palette, and humane willingness to “[see] you, but not [see] through you,” as writer Howard Jacobson put it, Heimans has painted everyone from Dame Elisabeth Murdoch to Tom Uren; Judi Dench to Vladimir Ashkenazy; Margaret Atwood to John Howard and Frederik, now Denmark’s King. While still a prince, King Charles III followed in his parents’ footsteps and also sat for him. “The [British Royal] family really adore him,” says Philip Bacon. “And they love those portraits.”

The day Heimans painted the Queen, she appeared a very long way away: toiling towards him down an endless corridor in Buckingham Palace. “She was with her entourage, and it’s such a long way she was almost invisible at the start, just this tiny little figure, but all sparkling because she’s wearing these diamonds that are throwing off the light from sun streaming through the windows. So, you’re standing there waiting for about five minutes; waiting for her to get to you in all her outfit.” She was wearing the robe of state she’d worn on entering Westminster Abbey for her coronation, and the diamond necklace and earrings each queen has worn on her coronation day since Queen Victoria. “And when she finally got to me, there was this surprising sense of a real person underneath the robe. Not an imperious person at all – something gentle, but shy, honest. She had soulful eyes. It’s not something you are prepared for.”

This moment, and the portrait that came from it, had its beginnings years before, when Justice Michael Kirby sat for Heimans in 1996. The resulting portrait has Kirby, robed and quizzical, standing slightly apart in a crowd of his judicial brethren. Kirby sat for Heimans while working one weekend; he agreed to look up from his desk on Heimans’ signal. “You will see a faint look of impatience across my face [in the painting],” Kirby acknowledges wryly. “This was not derived from my judicial work, where I displayed saintly patience, but from the interruption of my work by a very young Ralph Heimans.”

Radical Restraint (1998) is the only Heimans work that has ever met the criteria for entry to the Archibald. It was not even hung, though it made the final of the Doug Moran National Portraiture Prize in the same year. Heimans smiles. “I think [not being selected] had an effect on me at the time – a slightly chilling effect,” he says, “which is a bit silly. But I’m a huge supporter of portrait prizes as a concept, and the Archibald. I think it’s an incredible way for the public to engage in portraiture, and it keeps the tradition alive.”

With a fine disregard for judging-panel opinion, Kirby loved the painting. “[Heimans] is the Diego Velázquez of the current age,” he says. Radical Restraint was purchased by National Portrait Gallery in 2001, and the pair became friends. Years later, it was Kirby who started the artistic and diplomatic balls rolling that eventually resulted in the only portrait of the Queen done during her Diamond Jubilee year, painted by Heimans.

“When she finally got to me, there was this surprising sense of a real person underneath the robe. Not an imperious person at all – something gentle, but shy, honest.”

Ralph Heimans on the late Queen

It’s a striking work – not least because of its setting: the extraordinary Cosmati pavement in the high sanctuary of Westminster Abbey, where English monarchs have been crowned for more than 1000 years. Heimans spent two nights lying on the floor of the Abbey, recording its intricate details. “I wanted to reflect the singularity of her experience,” he says. “None of us knows what it’s like to be Queen, do we? Only she knows.”

Just three weeks after its hanging in Westminster Abbey, the painting was defaced by a men’s rights activist with lilac spray paint, who wrote “Help” across the Queen’s body. “When they rang, the first thing I asked was, ‘Did he get the face?’ ” recalls Heimans. “And he had.” But thanks to the durability and resilience of Heimans’ old-world materials, the damage wasn’t permanent. “Some of the paints I used on that portrait I made myself when I was 20,” he recalls. “And the oil in them dried incredibly fast and hard, so the spray paint didn’t absorb. The old stuff works!”

Five hundred years ago, portraits travelled the world – they were the influencer posts of their day. Part of an artist like Hans Holbein’s job, therefore – like Kim Kardashian’s – was to tell his audience stories via visual symbols: stories about wealth, power, preference.

In portraiture, these symbols have barely changed in half a millennium – and Heimans, predictably, loves them. “It’s about being able to contribute to a canon, to a pictorial language that has lasted for centuries,” he says. He uses gloves, for example, exactly as Holbein did, to denote wealth, luxury, and personal agency (see his portrait of Mary of Denmark, secretly pregnant and embracing her new royal role, compared with Holbein’s portrait of another Danish princess, Christina of Denmark, secretly preparing to refuse marriage to Henry VIII). If Holbein were to totter out of the TARDIS today, he would read a Heimans work, with its weight of symbolic language, as easily as a street sign.

Not everyone is keen on this kind of decoding, of course. In 2014, art critic Andrew Frost called Heimans’ portrait of outgoing governor-general Quentin Bryce “a shambles of hokey symbolism and compositional trickiness”.

“I think I still hold that opinion,” says Frost today. “There’s just so much going on in that painting it sort of detracts from the subject. It’s supposed to be a portrait, after all.”

Bryce herself, however, certainly doesn’t feel shortchanged. “Ralph is a genius,” she says firmly. “It is a privilege, seriously, to be painted by such an artist.” And Kevin Rudd loves the care with which Heimans surrounded him with meaningful objects: his Chinese vases, books, chess set (denoting politics, strategic thinking, worldly power) – even his beloved cat Louey. “That’s Ralph’s signature song,” he explains: “in the tradition of the 16th-century portraitists. Imagine if I’d put a skull in there, too, for mortality’s sake!”

Heimans himself, meanwhile, still remembers Frost’s review. “Yes!” he says, half-laughing, half-wincing. “It was brutal! Look, I think the symbolism in my paintings is there if you’re interested, but there’s nothing prescriptive about it. Portraits should be like novels: you should be able to read them on lots of different levels. Whether you want to peel the onion is totally up to you.”

Despite such criticism, he still loves public work. “I spend most of my time working alone, on paintings that disappear into the homes of whoever’s commissioned them, never to be seen again,” he points out. “And I do that because that’s how portraiture works, and portraiture is what I absolutely love. But at the end of the day, you’re like every artist: you’re trying to communicate with other people. Sharing your vision is integral to the whole process. So I love it when my paintings enter a wider public forum – because you’re entering into a dialogue with an audience.”

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What he wants his paintings to say, he concludes, “is something truthful. And because I paint people, I’m trying to express something true to their own sense of themselves, true to my impressions of them, and true to the people looking at the painting. Often you wonder if you’ve succeeded. Are you able to capture the public imagination with your vision? Have they understood what you’re trying to achieve?” He laughs. “Very often you walk away thinking, ‘Oh, maybe not.’ But that’s the goal.”

Maybe, in the end, that’s why we love portraits. Because if an artist does express that truth, it lasts 500 years.

To read more from Good Weekend magazine, visit our page at The Sydney Morning Herald, The Age and Brisbane Times.