A wide-eyed, wary Princess Diana (played by Kristen Stewart in the new film Spencer) – tick. A repressed and disapproving Prince Charles (Jack Farthing) – tick. Another tick for the ultimate scheming courtier played by Timothy Spall, but Amy Manson as… Anne Boleyn? Yes, the film does include Henry VIII’s second wife, who famously lost her head, and for many it’s an unexpected inclusion.


But there are reasons why a distressed Di really might have imagined she was talking with the ghost of Anne – and the movie chooses to depict that someone has left an old biography, Anne Boleyn: Life and Death of a Martyr as a warning beside her bed.

Never mind that the two are both iconic women, who married into the royal family and – as the film would have us believe – lived to regret it, or that they can both boast a legend to live on through the centuries. There are some other striking similarities – and some important differences, too.

The filmmakers didn’t invent the emotional connection between the pair

As biographer Tina Brown recounts, a friend remembered the young Diana Spencer getting him to drive her round and round Buckingham Palace. It would be rather fun to marry Prince Charles, she said, “like Anne Boleyn or Guinevere”. (You do wonder whether she knew how those two ended up?) But there is, after all, also a blood relationship – one of the Spencer ancestors was descended from Anne’s sister, Mary Boleyn.

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Anne and Diana both had sisters who caught the royal eye before them

Diana’s sister Lady Sarah Spencer famously turned down Prince Charles. Mary Boleyn, older sister to Anne, probably didn’t have that choice when King Henry decided to make her his mistress. But it may have been Mary’s fate – used for a few years, then cast aside with a damaged reputation – that made Anne so determined to hold out for a higher prize.

Mary Boleyn, older sister to Anne, was also mistress to Henry VIII. (Image by Alamy)
Mary Boleyn, older sister to Anne, was also mistress to Henry VIII. (Image by Alamy)

Neither really knew what they were getting into, and both were plagued by royal expectations

Anne Boleyn and Diana Spencer came from families with a tradition of service to the Crown, and both were from the aristocracy – Diana was an earl’s daughter, Anne was the Duke of Norfolk’s niece. But in the 1520s, the king was expected to marry a foreign princess for political advantage – and even in the 1970s, Prince Charles expected to marry a suitable girl such as Diana, rather than one he was in love with – as he famously stated, “whatever in love means”.

Both had causes they passionately believed in

Both Anne and Diana were known as style setters and fashion icons – but both had a far more serious side. Diana famously spoke for Aids sufferers and campaigned against landmines. Anne’s powerful commitment to religious reform led directly to Henry VIII breaking away from Rome and forming the Church of England.

Diana, Princess of Wales visits sufferers of Aids in Brazil
Diana, Princess of Wales was associated with number of causes, including speaking for sufferers of Aids. (Photo by Tim Graham Photo Library via Getty Images)

They both came up against the royal establishment

Diana famously blamed the ‘men in grey suits’ for her estrangement from the royal family; in the film, they’re epitomised by Timothy Spall’s Major Gregory. Anne Boleyn came up against the court faction – and up against Thomas Cromwell, who was no friend to the Boleyns, and with whom she clashed over approaches to the Dissolution of the Monasteries.

Both predicted their own death

In her distressed later years, Diana made wild suggestions of an assassination plot. (“Will they kill me, do you think?”, Kristen Stewart asks in the role. Though on the surface, it could be simply a jokey “will they kill me for being late for tea?”, many will surely regard it more sombrely). “Go! Run!”, the ghost of Anne tells Diana in the movie.

The real Anne – sent to the Tower of London, accused of treason and adultery – recalled predictions a queen of England would be burnt; though she also, pathetically, hoped she might be allowed to retire quietly to a nunnery.

Their deaths were not the end of the story

Both refused, you might say, to lay down and die. “She won’t go quietly,” Diana said of herself in the famous 1995 Panorama interview, and public reaction to her death seemed even to threaten the monarchy. Likewise, Anne remains one of the most fascinating figures in history and Protestant England is partly her legacy.

Diana, Princess Of Wales, Prince William And Prince Harry visit Thorpe Park amusement park. (Photo by Julian Parker/UK Press via Getty Images)

Both left children who carried their qualities

Anne’s daughter Elizabeth I dared to govern England alone, and in many ways she was as much of a rule-breaker (and as cultivated a woman) as her mother had been. In turn, Diana’s sons brought her warmth and relatability into the royal family – and perhaps, thinking of Prince Harry’s decision to step away from his official role in the royal family, her explosive impact on the modern monarchy, too.


Spencer is directed by Pablo Larraín and stars Kristen Stewart as Diana, Princess of Wales, and is in cinemas in the UK from 5 November 2021


Sarah GristwoodHistorian, biographer and broadcaster

Sarah Gristwood is a best-selling biographer, historian, and broadcaster, and a regular media commentator on royal and historical affairs. Her latest book is 'The Tudors in Love: The Courtly Code Behind the Last Medieval Dynasty' (2021)