Dan Llywelyn Hall was just 32 when he was commissioned by the Welsh Rugby Union to create the portrait of Elizabeth II, with the monarch sitting for him at Windsor Castle in 2012.
The artist’s royal works have since included a portrait marking William becoming a father, a live painting of the state funeral of the late Queen, and Charles’s coronation procession.
He has now produced 10 new portraits inspired by royalty throughout history for the Society of Antiquaries, with artist Adam Dant painting a further 10 works.
Their exhibition, titled The Reign, marks 150 years of the society at Burlington House in London’s Piccadilly and will be auctioned to support the cataloguing and digitisation of around 25,000 prints and drawings from the 18th and 19th centuries.
Two pieces by Llywelyn Hall feature contemporary royals Meghan, portrayed as Dame Elizabeth Grey, Queen of England by marriage, and Harry, depicted as Charles Edward Stuart, otherwise known as Bonnie Prince Charlie.
He said: “The royal family is possibly the most enthralling longest-running drama in history, the inspiration of theatre, books and every art form.
“It seemed that these figures caught on the knife edge of public opinion were ideal for drawing comparisons from distant monarchs – like the exiled princes and princesses of the past, that lurk in the background but are still irrevocably tied to the job.
“We can’t help ourselves and wonder whatever next?”
The piece featuring Meghan is entitled Returning White Queen and portrays her as Elizabeth Woodville, later known as Dame Elizabeth Grey, who was Queen of England by marriage to King Edward in 1464.
Harry is shown in a piece entitled Spectre Of The Bonny Prince, as Charles Edward Stuart, who was known as the Young Pretender and Bonnie Prince Charlie.
Llywelyn Hall said: “In Harry’s case, I have entered the story before he met Meghan – the young party-goer with his future very much in the balance, a bit like the Bonnie Prince I have likened him to.
“I thought putting Meghan in the role of the White Queen, who was a Queen Consort and possibly the most influential ‘outsider’ in royal history, might have a fine irony to it and not necessarily beyond the realms of reality.”
Reflecting on his previous and latest pieces of royal art, he said: “I see the subject of royalty utterly irresistible and rich succour for art.
“The funeral piece and the subsequent King’s coronation piece are part of that lineage and my part in interpreting our times.”
He acknowledged there is now a large amount of photography of the royal family but said a painting can have “greater authenticity”.
The Cardiff-born artist’s other pieces for The Reign include portraits of Mary I, Mary of Austria, Henry VI, and Anglo-Saxon king Athelstan, who ruled from 927 until his death in 939.
He has also included Llywelyn ap Iorwerth, known as Llywelyn the Last, one of the most powerful Princes of Gwynedd.
Llywelyn Hall said: “There are virtually zero depictions – painted or otherwise – of Welsh nobility and this was as frustrating as liberating.
“I drew inspiration from the written accounts that detail his capture and deception from the English King. Somehow the painting emerged as I read and imaged the torment and feelings that Llywelyn must have felt.
“Above all, his dignity is etched on his face and this portrait defined his image re-born.”
Llywelyn Hall described pieces held by the Society of Antiquaries, which has existed for more than 300 years, as “extraordinary riches” and “a treasure chest”.
– The Reign exhibition will open to the public at Burlington House in Mayfair, central London, from June 28, with a live auction taking place on July 4 with guest auctioneer Matthew Haley, a regular on the BBC’s Antiques Roadshow.
Bids can be made on https://the-reign.uk/.
