32 of the best stories from the royals meeting showbiz royalty, from Princess Diana's cheeky comments to stars breaking protocol

When the kings and queens of the showbiz world meet real royalty, a memorable encounter is sure to be had

L-R: John Travolta dancing with Princess Diana, Prince William and Taylor Swift, The Queen meeting Marilyn Monroe
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It's fair to say the Royal Family bring a level of unprecedented star power wherever they go.

From their best royal tour moments to the show-stopping royal gowns the royal ladies are snapped in, wherever they go, the cameras follow.

But, now and then, the royals collide with some of the biggest names in showbusiness and kick up a real media storm.

From Hollywood icons to music legends, many stars have shared what goes down when showbiz royalty meets actual royalty... 

32 of the best stories from royals meeting showbiz royalty

Barbra Streisand's rule-breaking cup of tea with King Charles

King Charles with Barbra Streisand

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When it comes to showbiz royalty, you don't get much more regal than Barbra Streisand - and her power even saw the then-Prince Charles break from protocol. 

In her memoir, My Name is Barbra, the actress recalls her experiences meeting the now King - and learning that he had a crush on her while at university. 

They first met in 1974 when Charles was on naval duty in San Diego and visited the recording studio in LA where she was recording the soundtrack for Funny Lady.

She writes, "The prince was utterly charming when he came to the studio, but frankly, it’s hard to have a real conversation when you’re surrounded by fifty photographers snapping pictures... I was drinking tea and offered him a sip… and the future king of England actually drank from my cup, which was apparently unprecedented."

My Name is Barbra - £16.00, Amazon

My Name is Barbra - £16.00, Amazon

Fancy reading about Barbra's encounters with King Charles, plus a whole host of famous faces and legendary names? It's all in her epic memoir, decades in the making. 

Lady Gaga's unlikely similarity with Queen Camilla

Queen Camilla meeting Lady Gaga

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Many people wouldn't imagine Queen Camilla and Lady Gaga have much in common - but in 2016, the then Duchess of Cornwall revealed to the pop star that they shared a name

While attending the Royal Variety Performance, Camilla is widely reported as telling the Bad Romance singer, "My grandchildren call me Gaga!"

Princess Diana once invited Cindy Crawford for tea

Cindy Crawford

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Princess Diana once invited the '90s supermodel Cindy Crawford - along with fellow fashion icons Christy Turlington and Claudia Schiffer - for tea at Kensington Palace as a birthday surprise for Prince William. Talk about a cool mum. 

"Princess Diana had somehow got the number to my office and called herself to ask for me. My assistant was in shock!" Cindy recalled in a moving Instagram post in 2017.

"I think Prince William was just starting to notice models and she thought it would be a cute surprise for him and Prince Harry."

Prince Philip's surprising request for Cate Blanchett

Cate Blanchett

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When Academy Award winning star Cate Blanchett was invited to Buckingham Palace, there was no way she could prepare for the conversations she'd have to field. 

Rather than discussing shared love for things like the environment (Cate has since joined forces with Prince William's Earthshot incentive), the late Prince Philip asked the Aussie star... how to work a DVD player. 

"There were 12 of us, and I couldn’t work out for the life of me why I’d been invited," the Oscar winner said in an episode of Jonathan Ross which aired in 2018. 

"I sat next to [Philip] and he said, ‘I hear you’re an actor? I was given a DVD player for Christmas and I can’t work out whether I put the green cord in or the red cord."

She added with a laugh, "I thought, 'He’s invited me to lunch to tell me about his DVD player!'"

Dawn French's hilarious (and rude) encounter with King Charles

Dawn French

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Dawn French is a beloved comedy icon - so of course she has a hilarious tale to tell involving a run-in with King Charles. 

Speaking on Virgin Radio in 2023, Dawn was explaining how the then Prince of Wales was at the same event and "he was coming down the line, greeting everybody."

Explaining how the rude joke came about, Dawn went on, "He started it because he had been to see A Midsummer Night's Dream that I was in. And he said to me, 'Well, the last time I saw you, I saw your Bottom', referring to the character Bottom in Midsummer Night's Dream, that I played."

"And I thought, 'Right, we're off.' And I said, 'Tonight, Sir, you will see my Beaver!'

At the time, Dawn was voicing the role of an animated Beaver in The Lion, The Witch and the Wardrobe. 

The Queen of Pop meets the Queen

Madonna meeting the late Queen Elizabeth II

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Not many people could get away with earnestly questioning who Madonna is - but that's what the late Queen Elizabeth reportedly did back in 2002 

While meeting the pop icon at the premiere of the James Bond film Die Another Day,  the late monarch questioned who she was, per the Daily Mail.

And when someone told Her Majesty that Madonna had performed the movie's theme song, she replied "Oh really, did you?" 

Still, it wasn't just Madonna who failed to strike a familiar chord. When the Queen then shook hands with actor John Cleese, who plays Q in the movie, she asked him, "And what do you do?"

Twiggy's awkward encounter with Princess Margaret

Twiggy collecting her Damehood

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Princess Margaret was the late Queen's younger sister and while the monarch was known for her reserve, Margaret was known for a rebellious streak. 

And 1960s model Twiggy found out all too awkwardly that Princess Margaret wasn't quite as polite as the Queen.

Recalling an incident when the pair met, Twiggy explained to The Express, "Princess Margaret asked, 'What's your name?' I said, 'My name's Lesley Hornby, Ma'am, but everyone calls me Twiggy.'"

"She just looked at me and said... 'Oh, how unfortunate'. Then she didn't talk to me again."

"I was mortified."

The royals made it up to Twiggy when she was presented with a Damehood in 2019.

Princess Diana and Billy Crystal crack jokes

Princess Diana meeting Billy Crystal

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Princess Diana was famed for her playful side - often rebuking stiff protocol to have fun on her own terms. And Billy Crystal, star of When Harry Met Sally, shared just how at ease she could make people. 

Speaking to People magazine, the legendary actor recalled Diana joking with him as the lights went down and the screening began at the London premiere of one of his movies.

"She whispered to me, 'I'm taking my shoes off.' So I went, 'I'm taking my pants off.' And she replied, 'Oh, you're so naughty!'" he said.

Lewis Hamilton gets a lesson from the late Queen

Lewis Hamilton

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Lewis Hamilton, the Formula One star, had lunch with the late Queen Elizabeth II in 2010 and revealed he got a lesson in some old-school etiquette.

While appearing on The Graham Norton Show, Lewis shared that Her Majesty knew about racing and liked to watch Lewis.

At his lunch, Lewis Hamilton actually had the honour of sitting right next to the Queen - but that didn't mean he could speak as freely with her.

"She was to my right and I started to talk to her and she's like, 'No, you speak that way first and I will speak this way and I come back to you,'" he explained. "So she spoke to the guy next to her for like five minutes and then she spent the rest of time talking to me."

Ed Sheeran breaks protocol with King Charles

Ed Sheeran collecting his MBE

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In December 2017, singer Ed Sheeran was made a Member of the Order of the British Empire (MBE).

He was presented with his honours from the then Prince Charles.

During the Investiture ceremony, Ed made a slight slip-up in terms of protocol by touching the now King's arm.

"Apparently, I did a big faux pas, though. I shook his hand and then grabbed it and you're not meant to do that," he shared on US television show, Today.

The cast of Top Gun are sent flying by the Prince and Princess of Wales

Prince William and Kate Middleton meet Miles Teller from Top Gun: Maverick

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Prince William and Kate Middleton attended the London premiere of Top Gun: Maverick in 2022, and they instantly charmed the Hollywood stars, including Miles Teller. 

Miles told Jimmy Fallon on The Tonight Show how "disarming" the couple were, and how he found himself lost in William's eyes. 

He said on the show, "Oh they give you like a full kind of rules, like do's and don'ts, and there's a lot of etiquette... You're not supposed to, like, extend your hand right off the bat unless - unless they do.

"But I felt the vibe, so I was like 'I'm going in, I'm going in,' and to their credit, they were very disarming."

Of a photo of them together, he joked, "right there I'm honestly lost in his eyes."

Serena Williams shares a special first with Kate Middleton

Serena Williams

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For Kate Middleton - a well-known tennis obsessive - meeting tennis legend Serena Williams in 2016 must have been special even for someone who has met all sorts of showbiz royalty. 

Kate's love of tennis could explain how Serena got away with pulling a historic first - recording a Snapchat video of the Princess of Wales! 

Per PEOPLE, Serena explained, "When I saw her, I wanted to take a picture with her. But then I was like, 'Should I do a picture or a Snapchat video?' Obviously, I opted to do that and it was fun!"

She added of Kate, "She was super sweet, super level, so beautiful - she was really nice."

Eddie Redmayne reveals a secret from Prince William's school days

Prince William with Eddie Redmayne at a polo match

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Eddie Redmayne is no stranger to the royals, having gone to school with Prince William and sharing a friendship during their time at Eton. 

However, after the pair were spotted catching up at an event, the Oscar-winning actor shared some new insight into what William's younger years were like. 

The star of The Danish Girl revealed to the Daily Mail William was actually a bit of a target. "I always felt slightly sorry for Will because everyone wanted to tackle the future King of England. He took all the hits."

Allison Janney's embarrassing encounter with Kate Middleton

Allison Janney

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Actress Allison Janney met Prince William and Kate Middleton at the BAFTAs in 2018, and she had a hilariously relatable moment with the then Duchess of Cambridge. 

"I did meet Kate and William, and she was in her heels and pregnant [Kate was pregnant with Louis at the time], so I felt like a bit of a wimp that I was there in my bare feet," the West Wing star said on an appearance on The Late Late Show. 

"I told her that I was in bare feet and I told her that she should take her shoes off 'cause she's pregnant. It was an awkward moment. I called her 'honey,' and that might not have been royal protocol."

Judy Garland's quick comeback for Princess Margaret

Judy Garland

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Princess Margaret's American tour in the 1960s was full of glamour and was generally considered to be a huge success. President Lyndon B Johnson said of the Princess during a White House dinner, "You have claimed our heart, and we are very proud to give it you...You have represented well the people that you serve with dignity and grace and spirit and joy."

However, she didn't quite endear herself to everyone across the Atlantic.

Per the Telegraph, Margaret's famed bluntness (plus her knack for keeping people waiting for hours at parties) led screen icon Judy Garland to reportedly call her "a nasty, rude little Princess."

And when Margaret demanded a sing-song from Judy, her epic retort has been suggested to have been, "Tell her I’ll sing if she christens a ship first."

David Duchovny has to explain a slang term to King Charles

David Duchovny

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Imagine having to explain the concept of a bootie call to a future King. Well, if you were the star of the X-Files, you don't have to imagine it. 

David Duchovny recalled the stranger-than-fiction encounter during an appearance on The Late Late Show in 2018. 

Seated next to the then Prince Charles back in the 1990s, the pair were watching British girl band All Saints sing their song, Bootie Call. David explained, "I saw Prince Charles was just kind of looking perplexed. And he said, 'Bootie call?' And I said, well, I can explain it to you, it's a little off-colour, but I can do it. And he said, 'Yes, please.'"

Shawn Mendes is left hanging by Queen Elizabeth

Shawn Mendes performing at the Queen's 92nd birthday concert

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Canadian tween icon Shawn Mendes might not exactly be the first name one would think of for the Queen's 92nd birthday gala, but he did indeed put on quite the show in 2018. 

However, he revealed things got quite awkward backstage with the late Queen.

"I'm standing there waiting to go on stage and the Queen just walks up next to me and she's standing there," Shawn revealed on an episode of The Ellen DeGeneres Show. 

Quoting the protocol of meeting a royal, he explained, "You're not allowed to speak to her unless she speaks to you first. So it was like this 10 minutes of very awkward silence between me and the Queen. She didn't look at me at all. I looked over a couple of times and I was like, 'I probably shouldn't even be looking.' It was super weird."

How Sir Elton John started his lifelong friendship with Princess Diana

Sir Elton John collecting his OBE

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Sir Elton John has been a close friend of the royals for decades, and it can be traced back to his great bond with Princess Diana. 

He famously sang at her funeral, and his specially recorded version of Candle in the Wind became the best-selling single of all time in the UK. 

While there are many anecdotes of Elton meeting royalty, how did it all begin? Writing in his memoir Me, the pop icon recalled his first ever meeting with Diana in 1981. 

It was for Prince Andrew's 21st birthday party at Windsor Castle and he describes how "she arrived in the ballroom and we immediately clicked. We ended up pretending to dance the Charleston while hooting at the disco's feebleness."

"She was fabulous company, the best dinner party guest, incredibly indiscreet, a real gossip: you could ask her anything and she'd tell you."

Emma Thompson's funny encounter with Prince William

Emma Thompson with Kate Middleton

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Emma Thompson has enjoyed several encounters with the royals over the years, but one of her most memorable ones involved some saucy jokes and an "inappropriate" noise. 

The actress previously revealed on The Ellen DeGeneres Show that she and Prince William had an awkward exchange when his attempt to pin her medal went a bit awry. 

Per Hello!, Emma joked, "He had to pin it on and it's a little bit of a nipple moment and you go, 'Gosh, I wasn't expecting that.' Then he pins another one underneath. And I'm pretty low-slung these days so both times it hurt." 

The hilarious actress then let out "a very loud and inappropriate noise inside Buckingham Palace."

At least it was distinct! 

Tom Cruise's close bonds with the royals over the years

Tom Cruise on the red carpet with Kate Middleton

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Tom Cruise has enjoyed a good relationship with the royals for years, and he has always spoken very highly of them. 

After meeting with William and Kate for the 2022 Top Gun: Maverick premiere, he reportedly shared his opinion of the Prince of Wales on the red carpet. "We have a lot in common, We both love England and we're both aviators, we both love flying," he said. 

One of his most memorable recent encounters was sending in a video cameo for King Charles' Coronation Concert. 

Tom, famous for his high-octane roles in films like Top Gun, gave the monarch a shout-out while in a fighter jet.

"Pilot to pilot, Your Majesty, you can be my wingman any time."

Margot Robbie's goof with Prince Harry

Margot Robbie

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Barbie star Margot Robbie has told the story of how she first met Prince Harry to different outlets, and it never gets any less amusing. 

The Australian actress, somehow, did not know who she was talking to after arriving at a star-studded housewarming for model Suki Waterhouse. 

As she has said to Entertainment Tonight, "I didn't know it was him for a half hour" and she actually cracked a joke about his ginger hair. 

"When I saw him in those glasses, I was like, 'Oh my god, I didn't know Ed Sheeran was at the party!'"

Kate Middleton makes Reese Witherspoon scream

Kate Middleton meeting Reese Witherspoon

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Legally Blonde's Reese Witherspoon has written about the "scream" she let out when she realised she was going to meet Kate Middleton. 

The pair were photographed together during a charity event in 2011, and Reese would go on to detail the regal encounter in her book, Whiskey in a Teacup. 

"I don't even know how I got so lucky as to receive the invitation.

"The scream that issued from my lips upon receiving it - you would have thought I was going to die."

As for how the now Princess of Wales was?  "She was just lovely and warm, elegant and composed. She also told a joke, and I immediately fell under her spell."

LeBron James' rule-break with Kate Middleton

Kate Middleton being presented a basketball jersey by LeBron James

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It was royalty on top of royalty when LeBron James - nicknamed the King - met the Prince and Princess of Wales in 2014. 

During William and Kate's tour of the United States, they caught a basketball game and met with the pro afterwards, where he presented them with their own 'Cambridge' jerseys - plus one for Prince George! 

LeBron was at ease with the couple, and even threw his arm around Kate, which some tried to make a deal of at the time. However, a palace spokesperson dispelled any talk of rule breaks. 

LeBron posted a photo of this monumental meeting on Instagram, writing, "This very moment will be forever remembered and put up in my house. It's all good and smiles on this side."

Marilyn Monroe meets Queen Elizabeth II

Queen Elizabeth II meeting Marilyn Monroe

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On October 29, 1956, two of the most photographed and immortalised women in history met. 

Marilyn Monroe and Queen Elizabeth II - who, perhaps surprisingly, were the same age - met at London's Empire Theatre. 

Town & Country report that the chatter was rather pleasant, covering subjects including being neighbours and the Queen’s beloved Windsor. "We love it," Marilyn said. "As we have a permit my husband and I go for bicycle rides in the Great Park."

Some attention has been called to Marilyn's choice of dress. 

While it was expected guests were told to dress conservatively, America's most famous blonde bombshell opted for her usual. Made of gold lamé, Marilyn's stunning gown was low-cut and full of cleavage. 

Princess Margaret and Elizabeth Taylor trade barbs

Princess Margaret meeting Elizabeth Taylor

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Another Princess Margaret celebrity encounter, another example of her ability to rub them up the wrong way - she was nothing if not consistent! 

According to Elizabeth Taylor biographers Sam Kashner and Nancy Schoenberger, Elizabeth's love for large jewels led to a memorable encounter between the two divas. 

Observing the Krupp Diamond ring, the iconic Asscher cut 33.19 carat stone, Princess Margaret is said to have said, "Is that the famous diamond? It’s so large! How very vulgar!"

However, she asked to try it on and was reportedly enchanted with the dazzling diamond. 

Without missing a beat, Elizabeth is said to have quipped, "Not so vulgar now, is it?" 

Taylor Swift sings with Prince William

Taylor Swift with Prince William

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Taylor Swift has enjoyed a few famous duets throughout her career, but perhaps one of the most surprising was her enjoying a rousing singalong with the future King. 

Taylor, William and Jon Bon Jovi joined forces for a surprise rendition of Bon Jovi's classic track, Livin' on a Prayer, during a palace gala. 

"I was surprised and flattered, and it felt surreal and completely natural at the same time," Taylor told the Daily Mail of the moment. 

"I still can't believe I've sung with Prince William."

Helen Mirren explains 'Queen-itis'

Helen Mirren

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Dame Helen Mirren has not only met the Queen, she's played her on two different occasions. 

However, that doesn't mean that a meeting with royalty is no less daunting. 

Revealing the story of how she was made a Dame Commander of the British Empire in 2003 (despite being one of the stars who initially turned down the honours), she explained "You get this thing called Queen-itis which is like a terrible virus that hits you the minute you are in front of the Queen."

While appearing on Jimmy Fallon's show, she continued, "You start saying weird things like 'it was terribly good fun,' and 'frightfully nice to meet you.' This weird voice comes out."

Anna Wintour keeps her sunglasses on - even with the Queen

The late Queen Elizabeth II and Anna Wintour

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Vogue's reigning queen met Queen Elizabeth for London Fashion Week in 2018 - and both stuck to their signatures. 

The late monarch wore a delightful, co-ordinated ensemble - including a pastel blue skirt and jacket - while Anna Wintour kept her trademark impenetrable sunglasses on. 

While some etiquette experts suggested Anna should have taken the glasses off, pictures from the event show the pair laughing and getting along great.

Ben Affleck doesn't realise his children's playmates were royalty

Ben Affleck

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Not every royal encounter is planned, as Ben Affleck discovered when living in London during the filming of Justice League. 

While appearing on a 2016 episode of Graham Norton, Ben Affleck revealed his son had some rather prominent playmates - unbeknownst to him. 

"It was pretty empty and then I noticed this weird vibe from the other grown-ups," the actor shared. 

"They were all very well-dressed and they had earpieces, and I thought, 'For a kids' place, this is tight security.' I was the very last person to realise that Prince George and Princess Charlotte were in there playing with my kid."

Michelle Obama's protocol breach with the Queen

The late Queen with President Barack Obama and Michelle Obama

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Michelle Obama meeting the Queen might have been nicknamed 'The Hug Heard Around the World' for all the headlines a seemingly normal gesture made. 

In 2009, Michelle Obama and then-President Barack Obama visited with Queen Elizabeth II at Buckingham Palace - and Michelle put a friendly arm around Her Majesty. 

In her memoir, Becoming, the First Lady recalled the event as just "two tired ladies oppressed by our shoes" after a day out and about in heels. 

Headlines made a great deal about the apparent breach of protocol, but Angela Kelly, the queen's dressmaker, addressed it in her book, The Other Side of the Coin: The Queen, The Dresser, and the Wardrobe. 

"In reality, it was a natural instinct for the Queen to show affection and respect for another great woman, and really there is no protocol that must be adhered to... When fondness is felt or the host of a State Visit goes to guide Her Majesty up some steps, it truly is about human kindness, and this is something the Queen will always welcome warmly."

The Other Side of the Coin: The Queen, the Dresser and the Wardrobe - £11.00, Amazon

The Other Side of the Coin: The Queen, the Dresser and the Wardrobe - £11.00, Amazon

Revised and updated to mark The Queen’s Platinum Jubilee, this special edition of The Other Side of the Coin contains chapters covering the Royal Household’s isolation during the pandemic, Angela’s own devotion to service to keep the monarch safe, and the light and laughter that was shared behind closed doors, even in the darkest moments.

Princess Diana dances with Travolta

Princess Diana dancing with John Travolta

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One of Princess Diana's most memorable moments came during a celebrity encounter with Grease star John Travolta, with the photo of the pair dancing up a storm at the White House immortalised forever. 

The iconic moment occurred when Diana and Prince Charles were on their official trip to the United States in November 1985 and were invited by the then President, Ronald Reagan, as guests to a gala dinner at the White House.

In an interview with Esquire Mexico, Travolta said, "The whole stage is like a dream. I go up to her, touch her on the shoulder, ask her to dance. She turns around and when she sees me she displays that captivating smile, somewhat sad, and accepts my invitation.”

"And there we were, dancing together like in a fairy tale. Who could imagine that something like this is going to happen to you one day? I was smart enough to register it in my memory as a very special, magical moment.”

The Spice Girls grab a handful of King Charles

King Charles with Geri Halliwell and Mel B from the Spice Girls

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Girl Power tore through the world in the 1990s thanks to five women - Sporty, Ginger, Scary, Baby and Posh. 

The Spice Girls were a cultural force, so it was only appropriate that they decided to do away with royal protocol when they met with the then-Prince Charles in 1997.

From the very off, Scary - aka Mel B - kissed the future King on the cheek, leaving a bright red lipstick mark.

Taking it one step further, in one of the most famous celebrity encounters with the royals (and perhaps even one of Charles's most memorable moments as a prince), Geri Halliwell then gave Charles a kiss... and a pinch on the bottom. 

Nearly two decades later, Ginger Spice - now better known as Geri Horner - wanted to make an important clarification. 

"I didn't pinch Prince Charles's bum, as was reported. I patted it."

Jack Slater
Freelance writer

Jack Slater is not the Last Action Hero, but that's what comes up first when you Google him. Preferring a much more sedentary life, Jack gets his thrills by covering news, entertainment, celebrity, film and culture for woman&home, and other digital publications.

Having written for various print and online publications—ranging from national syndicates to niche magazines—Jack has written about nearly everything there is to write about, covering LGBTQ+ news, celebrity features, TV and film scoops, reviewing the latest theatre shows lighting up London’s West End and the most pressing of SEO based stories.