They may be one of the most highly regarded families in the world, but the British royals aren’t immune to a bit of controversy.
From shock divorces to secret affairs and even a naked Vegas romp, we’ve seen the Windsors of all generations get up to some pretty shady stuff, but we’ve rounded up the top 50 best (or worst) ones for your reading pleasure.
How many do you remember?
1. Princess Margaret’s divorce from Antony
Her marriage to fashion photographer Lord Antony Armstrong-Jones, Earl of Snowdon, came to an end after 18 years in 1978, though they had been living separate lives for at least two years.
Margaret’s was the first modern divorce that plunged the monarchy into disrepute.
2. The Queen vs Camilla
Queen Elizabeth and her daughter-in-law have smoothed over their differences now, but for many years she refused to forgive Camilla for ruining Prince Charles’ marriage to Diana and dragging the monarchy’s good name through the mud.
According to Charles’ biographer Tom Bower, the Queen used to describe Camilla as “that wicked woman”.
The Queen used to describe Camilla as “that wicked woman”. (Images: Getty Images)
3. Prince Philip’s racist comments
There’s a long list of headlines about Prince Philip’s inappropriate comments over the years.
In 2002, he asked an Indigenous Australian “do you still throw spears at each other?”, while in 1986 he warned a group of British students that if they stayed in China any longer “you’ll be all slitty-eyed”.
4. Fergie’s toe-sucking shocker
While still legally married, a bikini-clad Fergie was snapped in August 1992 having her toes sucked by US financial adviser John Bryan.
The lurid pictures were splashed across a UK newspaper’s front page while she was holidaying with the royal family at Windsor. While Prince Philip is believed to have chuckled, the Queen instructed her private secretary to send her daughter-in-law back to London in disgrace.
5. Charles cheats on Diana with Camilla
After meeting in the 1970s, Prince Charles and Camilla Parker Bowles’ illicit affair resulted in the most infamous split of all time.
Princess Diana famously referred to Camilla as “the third person” in her marriage. While Charles and Camilla’s love affair was widely suspected, the extent of it was exposed when a 1989 recording of a private late-night phone conversation was leaked in 1993, in which Charles declared to Camilla that he wanted to “live inside your trousers”.
Princess Diana famously referred to Camilla as “the third person” in her marriage. (Image: Getty Images)
6. Philip and Elizabeth are cousins
Philip, who was born of Greek and Danish nobility, is related to his wife through Queen Victoria – her paternal great-great-grandmother.
Philip, meanwhile, also calls Victoria his great-great-grandmother through his mother’s side – making him and the Queen third cousins. They’re also second cousins once removed through King Christian IX of Denmark.
7. Princess Michael’s racist brooch
When Princess Michael of Kent met Meghan Markle, she didn’t make the best first impression.
The royal wore a racially insensitive brooch to the Queen’s Christmas lunch at Buckingham Palace in 2017. The piece of Blackamoor jewellery is considered offensive because it has connotations of slavery.
“Princess Michael is very sorry and distressed that it has caused offence,” a spokesperson said afterwards.
Princess Michael’s brooch made headlines in 2017. (Image: Getty Images)
8. Andrew dubbed ‘Air Miles Andy’
Definitely not his most shocking move to date (more on that later) but Prince Andrew has frequently the headlines for his ostentatious spending on helicopters.
Rather than paying less than $100 per trip on private chauffeurs in town cars, the Duke of York often insists on chartering a chopper, which can cost $10,000 or more.
9. King Edward VIII abdicates
In 1936, Queen Elizabeth’s path to the throne was forged when her uncle King Edward handed the crown to her dad King George VI.
Edward wanted to marry his American divorcee lover Wallis Simpson – a request which was forbidden by the Church of England, over which he presided. He chose love, put his younger brother in charge, and went on to live happily with Wallis until his death in 1972.
10. Prince Harry’s naked Vegas romp
By now firmly established as “the party prince”, Harry hit headlines in 2012 when he was photographed playing a game of strip billiards in a Las Vegas hotel room.
Harry was butt naked aside from a protective hand covering his, er, crown jewels. While most UK newspapers agreed to palace pleas not to run the photos, The Sun later went back on its promise, splashing the pics across their front page under the headline, “Heir it is!”
11. Prince Philip cheating on the Queen
Unconfirmed reports allege Prince Philip had an affair with stunning British showgirl Pat Kirkwood while the Queen was eight months pregnant with Prince Charles.
Some insiders claimed at the time the Duke of Edinburgh had even gifted his mistress with a Rolls-Royce. Pat denied the rumours until her death in 2007, though other sources say the Queen “allowed Prince Philip a lot of leeway”.
12. Margaret’s hard-partying health problems
The Queen’s younger sister was a social butterfly her entire adult life – and she paid for it medically. After feeling unwell in 1978, she was diagnosed with gastro and mild hepatitis.
A pack-a-day smoker since the age of 15, she had part of her lung removed in 1985. In 1993 she was rushed to hospital with pneumonia. By 2001 she had suffered several strokes, leaving her partially paralysed. She died aged 71 in 2002.
Princess Margaret was a pack-a-day smoker since the age of 15.
(Image: Getty Images)13. Sophie of Wessex’s topless bombshell
The Queen’s youngest son Prince Edward has managed to keep his nose squeaky clean of all controversy, but the same can’t be said for his wife, Sophie, the Countess of Wessex.
Just weeks before her 1999 wedding, a picture of Sophie with her bikini top pulled up by a TV host from 1988 appeared in The Sun. The palace insisted it was a cruel breach of privacy.
14. Diana and Charles get divorced
Prince Charles and Princess Diana announced their intention to “separate amicably” but not divorce in December 1992. But by 1995, sick of their public war of words and lurid tabloid headlines, with both having admitted to adultery, the Queen forced them to legally split.
A palace statement said, “After considering the present situation, the Queen wrote to both the prince and princess earlier this week and gave them her view, supported by the Duke of Edinburgh, that an early divorce is desirable.”
Charles and Diana during their last official trip together. (Image: Getty Images)
15. Prince William busted with Aussie blonde
The Duchess of Cambridge was less than impressed when footage of her husband Prince William dancing with other women on a boys’ ski trip surfaced online.
In the 2017 footage, William can be seen “partying” with NSW Central Coast model Sophie Taylor while Kate was at Kensington Palace with their two children.
16. Harry’s derogatory remarks
Philip isn’t the only royal who’s faced a backlash for using culturally sensitive language.
In 2006, the former army officer was recorded on video describing a Pakistani member of his platoon as “our little Paki friend… Ahmed”. In a separate clip, he is heard describing a solider wearing a cloth as looking “like a raghead” – a racist term for Muslims wearing their cultural headwear.
After the now defunct News Of The World released the clips in 2009, Harry apologised via a spokesman, who said the prince “understands how offensive this term can be”.
17. Diana secretly collaborates on a bombshell book
Andrew Morton’s 1992 biography Diana, Her True Story shockingly lifted the lid on Prince Charles’ extramarital affair with Camilla and Diana’s suicide attempts and eating disorders.
But it was only after her 1997 death the author revealed the princess had secretly been his source all along. He declared Diana sent him notes and photographs, and approved the pages through a middle man, so she could truthfully state she had never met him.
The tell-all book was released in 1992. (Image: Getty Images)
18. Princess Anne refuses to give her kids royal titles
Anne proved she wasn’t going to toe the royal line when her children Peter and Zara were born, refusing to give them royal titles.
Zara Tindall has since applauded her mum’s decision, defiantly insisting that even though she’s close with her grandmother the Queen, and can drop into a curtsey with the best of them, she’s “glad” she’s not a royal.
19. Diana’s affair with James Gilbey revealed
In 1992, The Sun exposed what became known as “Squidgeygate” – Diana’s affair with gin company heir James Gilbey.
In recordings of their private conversations, in which James calls her “squidgy”, Diana is heard explaining, “I just felt so sad and empty and thought, ‘Bloody hell, after all I’ve done for this f**king family…’ It’s just so desperate…He makes my life real torture, I’ve decided.”
20. Fergie says eight-year-old Beatrice is too fat
Sarah “Fergie” Ferguson raised eyebrows when she described her then-eight-year-old daughter Beatrice as “chunky”.
“I mean, she is only eight, but she definitely can pack it on a bit,” she said. “Poor baby. I think overeating sort of runs in the family.”
After becoming the face of Weight Watchers herself, Fergie revealed she had put Beatrice on a diet but the company soon spoke out to confirm that they didn’t condone the duchess’ actions.
21. Meghan’s dad dodges her wedding
Meghan Markle was devastated when her dad Thomas Markle Sr pulled out of walking her down the aisle at the last minute before her wedding to Prince Harry.
Accused of setting up paparazzi pictures and complaining of heart problems, the former lighting technician is said to have told his daughter in a tearful call he wouldn’t be making the trip from his Mexico home for her dream wedding.
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Thomas Markle famously pulled out of the royal wedding at the last minute.
22. A very underaged Charles caught boozing
Prince Charles would be grateful that smartphones weren’t invented when he ordered a cherry brandy in a local pub – when he was just 14. He would have gotten away with it, too, if a tabloid reporter wasn’t enjoying a beer a few barstools away!
In an interview with Vanity Fair years later, Charles said, “I said the first drink that came into my head, because I’d drunk it before, when it was cold, out shooting.”
READ MORE: Prince Charles’ biggest royal scandals to date.
23. Fergie sells access to Andrew
The News Of The World exposed the Duchess of York as asking for $850,000 in exchange for introducing reporter Mazer Mahmood – who was posing as a sheik – to Prince Andrew.
“That opens up everything you would ever wish for. I can open any door you want, and I will for you,” she was recorded saying in May 2010. “Look after me and he’ll look after you. You’ll get it back tenfold.”
Sarah apologised for her “serious lapse in judgement”, while Andrew insisted he had no knowledge of his ex-wife’s dirty dealings.
24. Diana self-harms while pregnant
Princess Diana admitted she “threw herself down the stairs” to “get Charles’ attention” while she was four months pregnant with Prince William. She recorded the grisly revelation on tape and sent it to journalist Andrew Morton, who later printed the claims in his book.
She alleges she told Charles, “I felt so desperate and I was crying my eyes out. He said I was crying wolf. ‘I’m not going to listen,’ he said. ‘You’re always doing this to me. I’m going riding.'”
Diana insisted that even though she was bruised, she knew she wouldn’t lose William.
Diana confessed to self-harming during her pregnancy with Prince William. (Image: Getty Images)
25. Andrew’s relationship with Koo Stark
In 1981, Prince Andrew began wooing risque actress Koo Stark. While the Queen was said to be enamoured by the pretty American, the British public were outraged by the idea of Andrew marrying a woman who enjoyed posing in semi-nude photoshoots.
26. Harry busted after teachers do his homework!
The palace was rocked by claims from teachers at Prince Harry’s posh Eton College that he “routinely cheated his way through school”.
Among the accusations was one from former teacher Sarah Forsyth, who felt the way she was “encouraged” to “prepare text” for Harry’s work was “unethical” – but at the time said, “I assumed I had been asked to do this because he was a weak student.”
27. Kidnap attempt on Princess Anne
The Queen’s daughter narrowly avoided being kidnapped in 1974 when a mentally ill, gun-toting man rushed at her car outside Buckingham Palace. Four people were shot, including her driver, a policeman, a bodyguard and a journalist. Anne escaped unharmed.
28. James Hewitt –Harry’s real dad
Due to their strikingly similar good looks and the timing of Diana’s affair, whispers have dogged Harry for years that James Hewitt, not Prince Charles, is his real father.
Harry has refused to talk about it, while the UK’s Daily Star recently “confirmed” Charles is Harry’s father, after consulting with hereditary features experts who say the prince shares telling features with his paternal grandfather Prince Philip.
29. Kate and Wills split
After falling for each other at university in 2001, Prince William and Kate Middleton seemed destined to marry – until they shocked the world by splitting up in 2007.
Before telling the media, Wills was seen jumping on a table in a London club yelling, “I’m free!” before suggesting his buddies join him in drinking the entire drinks list. Kate, meanwhile, let her hair down, too – choosing skimpier outfits and hitting the London social scene with sister Pippa in tow.
William soon realised what he was missing – they were back together three months later and engaged in October 2010.
WATCH: Prince William and Duchess Catherine talk about their brief break up. Post continues…
030. Mike cheats on Zara
When the Queen’s favourite granddaughter Zara shacked up with British rugby star Mike Tindall, royal insiders predicted trouble would follow – and it did.
During a New Zealand tour, Mike and a blonde woman were caught on video behaving like a “smooching teenage couple”. She turned out to be his ex.
31. Meghan’s ‘Markle Sparkle’ drug-peddling cousin
Critics have accused the Duchess of Sussex’s nephew Tyler Dooley of cashing in on his aunt’s royal status.
The 25-year-old released a strain of marijuana called “Markle Sparkle” out of his Oregon-based weed farm, where selling the drug is legal.
32. Duchess of Sussex’s porn scandal
The royal family immediately complained when a short clip of Meghan’s almost-topless scene from her TV show Suits was uploaded onto website Pornhub – prompting The Sun to declare, “Harry’s Girl on Porn Site”, in November 2016.
Three months later, the paper copped a firm slap on the wrist from the palace’s press department and issued an apology saying, “We would like to make clear that Miss Markle has never been involved with such content and had no idea the video had been published illegally on this website.”
Caught in the act Your Highness! (Image: Getty Images)
33. Margaret’s many affairs
It’s no wonder Margaret’s marriage fell apart, thanks to several reported affairs.
Her first dalliance was said to be with her daughter Sarah’s godfather, wine producer Anthony Barton, in 1966. A year later she had a fling with Robin Douglas-Home, a jazz pianist who took his life 18 months after they split, suffering from depression. Margaret also had an eight-year affair with Roddy Llewellyn, causing British MPs to label her a “floozy” and a “royal parasite”.
34. Royal ties with Nazis
Edward and Wallis, who were begrudgingly bestowed with the title of the Duke and Duchess of Windsor when they married, were widely reported to be “Nazi sympathisers” and personal friends of murderous Adolf Hitler.
A video, believed to have been shot in 1934, was obtained by The Sun, in which it appears Edward is teaching a young Princess Elizabeth to do the Nazi salute. The Queen’s husband Prince Philip went to school in Nazi Germany, while his sister was an outspoken follower of the anti-Semitic regime that resulted in the Holocaust.
Edward and Wallis were close with Adolf Hitler. (Image: Getty Images)
35. Diana suffers from bulimia
Diana has attributed her bulimia to finding out about Prince Charles’ affair with Camilla.
“Everyone in the family knew about the bulimia. And everyone blamed the failure of the marriage,” she said, describing throwing up her meals as the most “discreet” way of self-harming.
36. Harry goes to rehab
After a then-underage Prince Harry admitted to using marijuana and drinking alcohol after hours in a pub while he was at Eton College, Prince Charles taught him a lesson by sending him to the Featherstone Lodge drug and alcohol rehab facility in 2001 for one day to “shock” him – except the press got hold of the story not long after.
2“This is a serious matter, which was resolved within the family,” a spokesman said at the time.
Remember when a young Prince Harry went to rehab? (Images: Getty Images)
37. Margaret’s true love was a married man
The Queen’s sister fell in love with their late dad King George’s equerry, Captain Peter Townsend – the only problem was he was already married with two sons.
As soon as news of their affair broke, which began the year after King George died, Peter split from his wife Cecilia Pawley and proposed to Margaret. But the Queen, influenced by British parliament and the Church of England, denied Margaret’s request to marry a divorcee. Peter later married a Princess Margaret lookalike.
38. Charles dated Diana’s sister
Before Charles married teen kindy teacher Lady Diana Spencer, he carried a torch for her older sister Lady Sarah McCorquodale.
Their brief dalliance in the 1970s ended when she reportedly told Charles she’d never marry him – “if he were the dustman or the King of England”.
Prince Charles and Lady Sarah were an item for nine months. (Image: Getty Images)
39. Diana accuses Royals of plotting to take her sons
In the shocking documentary Diana: In Her Own Words, the princess revealed she was paranoid she would be separated from her sons.
3“Friends on my husband’s side were indicating I was unstable, sick and should be put in a home of some sort in order to get better,” she said. “There is no better way to dismantle a personality than to isolate it.”
And Dr James Colthurst, who knew her from the age of 17, confirmed she feared there was a plot to take William and Harry away from her.
“Her character was being written down – as she saw it, a campaign to sideline her and remove her from the boys,” he said. “That was her worry, that she was going to lose the boys.”
40. Harry’s Nazi costume
Historic headlines damning the monarchy’s ties to the Nazis didn’t deter Prince Harry from wearing a swastika armband as part of a dress-up party outfit in 2005.
When photos from the soiree were leaked, Harry released a grovelling mea culpa, saying, “It was a poor choice of costume and I apologise.”
In his Harry & Meghan docuseries that came out December 2022, Harry revisited the scandal, admitting it was ”one of the biggest mistakes of my life.”
”I felt so ashamed afterwards,” he shared.
”All I wanted to do was make it right. I sat down spoke to the Chief Rabbi in London, which had a profound impact on me. I went to Berlin and spoke to a Holocaust survivor. I could have just ignored it and gone on and made the same mistakes over and over again in my life. But I learned from that.”
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Harry’s Nazi costume was the talk of the town (if not the world) in 2005. (Image: Getty Images)
41. Wills forces secret girlfriend Kate to watch him flirt
When Prince William turned 21, he threw an Out Of Africa-themed birthday bash. But it wasn’t Kate who was the apple of his eye.
Instead, his former fling Jecca Craig acted as the guest of honour and sat beside him, while Kate was just a guest. It came after the palace denied that William and Jecca were romantically involved.
42. Harry scuffles with photographers
Prince Harry made it clear he’d had enough of the paparazzi when he left London nightclub Pangea one night in 2004 and got into a scuffle with a snapper outside. Clarence House claimed the young royal had been defending himself.
“Prince Harry was hit in the face by a camera as photographers crowded around him as he was getting into a car,” it said in a statement.
However, photographer Chris Uncle insisted, “He lashed out and then deliberately pushed my camera into my face.”
Young Harry got into a scuffle with a photographer outside a London nightclub in 2004. (Image: Getty Images)
43. Meghan’s family barred from the royal wedding
When Meghan married Prince Harry, her side of the chapel was noticeably bereft of Markles. The only family member invited was her mum Doria Ragland, much to the chagrin of her half-brother Thomas Markle Jr and half-sister Samantha Grant.
5Her aunt Tracey Dooley and nephews Thomas and Tyler made the trip to London, despite not being invited. Tyler sparked a police probe when he carried a knife into a nightclub.
44. Fergie banned from Will and Kate’s big day
Given the “fake sheik” scandal was yet to cool when William and Kate announced their engagement that same year, the couple decided it was best to leave Aunty Sarah Ferguson off the 1900 guest list for the Westminster Abbey extravaganza.
Rumour has it Wills had never been a fan of Fergie, who reportedly fell out with his mum Diana just before her death.
WATCH: Fergie talks to Oprah about her royal wedding snub. Post continues…
45. Assassination attempt on the Queen
The Queen expertly handled an assassination attempt while she was riding in the 1981 Trooping the Colour parade.
Marcus Sarjeant, 17, fired six blank shots at her as she rode down the mall, spooking her beloved mount called Burmese. When royal protection officers took down the wannabe assailant, he told them, “I wanted to be famous – I wanted to be a somebody.”
46. Kate’s Uncle Gary busted with cocaine
Kate’s uncle Gary Goldsmith dragged the Middleton clan’s name into disrepute when he was caught cutting up cocaine in 2009 at his Ibiza mansion.
6During the tabloid newspaper sting, he boasted that because of his royal niece he was expecting to be bestowed with the title “Duke of Slough”.
47. Andrew accused of sexual assault
In 2015, a US judge ordered allegations of sexual assault against Prince Andrew to be struck from the record. The allegations were made by Virginia Roberts, who claimed the incident occurred when she was 17.
Both Buckingham Palace and Andrew vehemently denied the claim. As part of the wider lawsuit, Virginia had accused Andrew’s former friend, convicted paedophile and billionaire businessman Jeffrey Epstein, of using her as a “sex slave”.
Prince Andrew vehemently denied the claims. (Image: The Mail on Sunday)
48. Mark Phillips’ love child
Princess Anne’s husband Captain Mark Phillips conceived a love child – a daughter named Felicity – during a one-night stand with New Zealander Heather Tonkin in 1984.
It is not known whether he – or his children with Anne, Zara and Peter – have ever acknowledged their relative Down Under. Zara and Felicity, who look strikingly similar, also share a love of horses.
49. Mike caught in ‘dwarf- tossing’ furore
On the same ill-fated trip to New Zealand where he was busted kissing his ex (see 30), Mike and his rugby buddies were caught getting involved in a boozy “dwarf-tossing contest”. For his actions – and lying to England Rugby Union officials about his encounter with his ex – Mike was fined $45,000.
50. Princess Diana’s death
Mystery still surrounds Diana’s tragic passing at the age of 36 in a Paris car crash in 1997, which also killed her lover Dodi Fayed.
7Some say it was caused by an aggressive paparazzi pack, that her driver was drunk, or the outlandish claim the royals had her killed because she knew too much about the monarchy’s inner workings.
While Dodi and driver Henri Paul died instantly, the princess was still alive several minutes after the fiery wreck. One of the first responders to the scene last year revealed her last words were, “My God, what’s happened?”
51. Prince Harry and Duchess Meghan’s Oprah interview
A year after stepping back from their senior royal roles, Prince Harry and Duchess Meghan took part in an explosive sit-down interview with Oprah Winfrey in March 2021.
The Diana Panorama style interview delved into several troubling revelations about their lives in the palace.
The main, and most jarring revelations from the interview included:
Someone in the royal family made troubling comments about the colour of baby Archie’s skin, before he was born. According to Meghan, Harry was involved in the frankly sickening conversation. “They were saying they didn’t want him to be a prince, which would be different to protocol, and that he wasn’t going to receive security. This went on for the last few months of our pregnancy,” Meghan revealed.
Meghan had suicidal thoughts following the horrific falsities and lack of support within the royal fold. “I just didn’t want to be alive anymore. That was clear and real and frightening and constant thought.”
Harry and Meghan were married in secret three days before the royal wedding
It was Kate Middleton who made Meghan cry just before her wedding, not the other way around as was reported by multiple tabloids at the time
The Duke and Duchess revealed the gender of their soon-to-be second child – a baby girl, who is due in the Australian winter.
Prince Charles stopped taking Harry’s calls when he tried to talk to him about stepping back from his senior royal role
Harry said he didn’t even realise he was trapped until he met Meghan – “I was trapped and I didn’t know I was trapped… My father and my brother, they are trapped, they don’t get to leave,” he said in the interview.
Harry still hopes to reconcile his rift with his elder brother and future King, Prince William.
