19 Unforgettable Celebrity Encounters with the Royal Family—And the Moments That Broke Royal Protocol

In 1956, Marilyn Monroe had a brief but historic meeting with Queen Elizabeth II in London, just three years after the Queen’s coronation. The two iconic women shook hands at a glamorous event — the Royal Film Performance of The Battle of the River Plate.

The event took place at the Empire Theatre in Leicester Square, a major venue for London film premieres. This special night brought together Hollywood royalty and British royalty, creating one of the most unforgettable moments in celebrity and royal history.

Even though their meeting was short, it remains a powerful image of two legendary figures from different worlds coming together during a time of global glamour and elegance.

#4 Taylor Swift And Travis Kelce With Prince William, Prince George, And Princess Charlotte

In one of the latest and most talked-about celebrity royal encounters, Taylor Swift met with Prince William and his two children — Prince George and Princess Charlotte — backstage at her sold-out Wembley Stadium concert on Friday, June 21. The event was one of eight shows that the Karma singer is performing in London as part of her global Eras Tour.

After the show, the Royal Family smiled brightly for the camera as Taylor captured a selfie that quickly went viral. In another photo shared on Taylor Swift’s Instagram, her boyfriend — NFL star Travis Kelce — also appeared, adding even more excitement for fans of pop music and sports celebrities alike.

This wasn’t the first time Taylor met Prince William. Back in 2013, she performed “Livin’ on a Prayer” alongside the Prince and rock legend Jon Bon Jovi at a Centrepoint charity event held at Kensington Palace.

These royal-meets-celebrity moments continue to attract huge attention across entertainment news, social media trends, and royal family updates, making them prime topics for fans and digital audiences worldwide.

#5 Prince Harry And Prince Charles With Victoria Adams “Posh Spice” And Mel C “Sporty Spice”

Back in 1997, during a royal tour of South Africa, Prince Harry and then-Prince Charles (now King Charles III) met with the world-famous English girl group, the Spice Girls. The meeting quickly made headlines—not just because of the celebrity presence, but also due to a playful break from royal protocol.

Geri Halliwell and Melanie “Mel B” Brown surprised everyone by giving Charles a kiss on the cheek, a move that’s usually not allowed when meeting members of the British royal family.

Years later, in a 2022 interview with People Magazine, Melanie “Mel C” Chisholm laughed about the moment, saying:

“Now that Charles is our King, it kind of makes it even more naughty. Those naughty Spice Girls!”

In his best-selling memoir, Spare, Prince Harry reflected on the event and said the cheeky moment actually helped. It gave his father “some positive headlines, which he sorely needed” after his high-profile divorce from Princess Diana.

This unforgettable meeting remains one of the most talked-about celebrity royal encounters, often referenced in entertainment news, pop culture throwbacks, and British monarchy media coverage.

#6 Queen Elizabeth II Meets Lady Gaga

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In 2009, Lady Gaga had a memorable meeting with Queen Elizabeth II during the Royal Variety Performance, a yearly event in the United Kingdom that supports the Royal Variety Charity. This charity helps people from the entertainment industry who are elderly, ill, or struggling financially.

For the grand event, Gaga turned heads with a dramatic red latex outfit, featuring large puff sleeves, matching rhinestone eyeshadow, and pointed-toe boots. It was a bold and unforgettable celebrity fashion moment.

Speaking with Vogue in 2021, the Applause singer explained her inspiration:

“I was meeting the Queen, and I wanted to dress like a queen in British fashion, and I also wanted to do it my way.”

The meeting was one of the most iconic celebrity and royal family encounters, blending pop culture with royal tradition, and it continues to be a highlight in both entertainment history and British royal event coverage.

#7 The Beatles Meet Princess Margaret And Queen Elizabeth II

During the Royal Variety Performance in 1963, The Beatles delivered one of their most famous on-stage jokes. As they performed in front of Queen Elizabeth II, John Lennon cheekily told the crowd:

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“The people in the cheaper seats, clap your hands… and the rest of you, if you’d just rattle your jewelry.”

The joke made the Queen smile and instantly became a legendary moment in both rock music and royal event history.

Just two years later, in 1965, all four members — John Lennon, Paul McCartney, George Harrison, and Ringo Starr — were honored as Members of the Order of the British Empire (MBE) by the Queen for their contributions to British music and culture.

However, in 1969, John Lennon made headlines again when he returned his MBE medal in protest of Britain’s involvement in the Nigerian Civil War, as well as the UK’s political actions in Vietnam.

This powerful combination of celebrity recognition and political protest remains a defining story in the world of entertainment news, British music history, and royal honors and controversies.

#8 Frank Sinatra Greets Queen Elizabeth II

The legendary musician first met Queen Elizabeth II in 1958 during the London premiere of Me and the Colonel, held at the famous Odeon Theatre in Leicester Square. The event was one of many glamorous red carpet moments where British royalty met global entertainment stars.

Their paths crossed again in 1983, this time at the 20th Century Fox studios, marking another chapter in the long history of celebrity and royal meetings.

These encounters highlight how Queen Elizabeth II remained a central figure in both British cultural life and major international entertainment events for decades.

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#9 Rihanna And Prince Harry

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In 2016, Rihanna — born Robyn Rihanna Fenty — met Prince Harry during the Golden Anniversary Spectacular Mega Concert at the Kensington Oval Cricket Ground in Bridgetown, Barbados. The event celebrated 50 years of independence for Rihanna’s home country.

For this special royal visit, Rihanna wore a blue dress and yellow nail polish, proudly representing the colors of the Barbados flag. Sitting beside Prince Harry, the global superstar made a powerful fashion and cultural statement that captured global media attention.

Their meeting became one of the most memorable celebrity royal encounters in the Caribbean, highlighting Rihanna’s pride in her roots and Prince Harry’s connection to the Commonwealth nations.

#10 Harrison Ford With Queen Elizabeth II

In 1978, a legendary Hollywood actor respectfully bowed to Queen Elizabeth II during the London premiere of Steven Spielberg’s hit sci-fi film, Close Encounters of the Third Kind. The event was a major film industry moment, drawing global attention as British royalty and Hollywood stars came together.

The meeting between the Queen and the actor became an iconic celebrity royal moment, remembered for its elegance, tradition, and the merging of cinema and royalty at a time when Spielberg’s film was making waves in global box office news.

#11 Barbra Streisand And Queen Elizabeth II

In 1975, Barbra Streisand, the rare EGOT winner (Emmy, Grammy, Oscar, and Tony), respectfully bowed to Queen Elizabeth II and Prince Philip during the London premiere of her film Funny Lady. The red carpet event was a highlight in both royal red carpet history and Hollywood cinema milestones.

In the movie, Streisand played Fanny Brice, a famous American comedian and performer, best known for creating the popular radio comedy series The Baby Snooks Show.

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The moment captured international headlines, merging the glamour of British royalty with the star power of one of America’s most celebrated entertainers, and remains a timeless memory in celebrity-royal encounters and London film premiere history.

#12 David Duchovny Explained Booty Calls To Prince Charles

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In one of the funniest and most unexpected celebrity-royal encounters, X-Files star David Duchovny once gave Prince Charles (now King Charles III) a quick lesson in modern slang — specifically, the term “booty call.”

The moment happened in the 1990s when the actor attended an All Saints concert with the royal. During the show, the group kept repeating the phrase “booty call,” which seemed to confuse the future king.

In a 2016 interview with James Corden, Duchovny recalled the exchange:

“I saw Prince Charles just kind of looking perplexed. And he said, ‘Booty call…’ and I said, ‘Well, I can explain it to you. It’s a little off-color, but I can do it.’ And he said, ‘Yes, please.’”

David then explained:

“It’s when a man or a woman calls a man or a woman to come to their home late at night for the express purpose of getting together—and then leaving right afterward.”

Prince Charles simply responded, “…Oh!”

This hilarious moment perfectly captures the generation gap between royalty and pop culture, making it one of the most unforgettable and humorous royal encounters in recent memory — and a favorite among fans of celebrity interviews, British royals, and 90s entertainment history.

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#13 Prince Harry Meets Kanye West And Sean “P Diddy” Combs

In one of the most unexpected celebrity-royal moments, Prince Harry was photographed in 2007 alongside Diddy and Kanye West (Ye) during an event honoring his late mother, Princess Diana. The photo also included Prince William, marking a rare mix of royalty and hip-hop icons.

At the time, this gathering was already surprising. But looking back now — especially after Diddy was sued in a $30 million sex trafficking lawsuit on February 26 — the moment feels even more unbelievable.

The event was held to celebrate Princess Diana’s legacy, but the guest list made headlines for blending the worlds of royal family tributes, music industry celebrities, and pop culture icons in a single photo that few could have predicted.

This image remains one of the most unforgettable photos of 2007, often revisited in discussions about celebrity-royal crossovers, controversial figures, and surprising moments in British royal history.

#14 Queen Elizabeth II Visits The Game Of Thrones Set And Cast

In 2014, Queen Elizabeth II and Prince Philip made a surprise visit to the set of HBO’s hit series Game of Thrones in Northern Ireland, one of the show’s main filming locations. Their visit quickly became a highlight in the world of celebrity-royal encounters.

During the tour, the royal couple met several key cast members, including Conleth Hill (Varys), Kit Harington (Jon Snow), Rose Leslie (Ygritte), and Maisie Williams (Arya Stark). They also spoke with the show’s executive producers and screenwriters, David Benioff and Dan Weiss.

The visit was widely covered in entertainment news, blending royal tradition with modern pop culture, and remains one of the most iconic TV show set visits by British royalty.

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#15 Madonna Shakes Hands With Queen Elizabeth II

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In 2002, real-life royalty met music royalty when Queen Elizabeth II greeted Madonna — often called the Queen of Pop — at the world premiere of the James Bond film Die Another Day.

The glamorous event took place at the iconic Royal Albert Hall in London, drawing global media attention. Madonna not only attended as a celebrity guest, but also performed the movie’s official theme song, adding to the significance of the moment.

This unforgettable meeting between British monarchy and international music royalty became a highlight in both royal event history and entertainment news, perfectly blending Hollywood glitz with royal tradition.

#16 Margot Robbie Talked To Prince Harry And Didn’t Recognize Him

In a hilarious case of mistaken identity, Barbie star Margot Robbie once partied with Prince Harry at Suki Waterhouse’s Christmas bash in 2016 — but didn’t realize who he was at first.

During an interview with Jimmy Fallon, Margot shared the funny moment:

“When I saw him in those glasses, I was like, ‘Oh my God, I didn’t know Ed Sheeran was at the party.’ And he was really offended. He was like, ‘Shut up!’”

She added with a laugh:

“I’d had a drink—or drinks. I thought I was hanging out with Ed Sheeran. I was thinking, ‘Ed’s a really cool guy. I’m going to take some pictures with him.’”

This unexpected celebrity royal encounter remains one of the most talked-about and funniest moments involving Prince Harry, blending Hollywood stars, British royalty, and a light-hearted case of celebrity confusion.

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#17 Prince Harry And Meghan Markle Meet Beyoncé And Jay-Z

In 2019, the Duke and Duchess of Sussex, Prince Harry and Meghan Markle, met Beyoncé and Jay-Z at the European premiere of The Lion King in London. The event was one of the most glamorous celebrity-royal encounters in recent memory.

Beyoncé voiced Nala in Disney’s live-action remake of the beloved classic, making her a central figure at the premiere.

According to a source who spoke to E! News, there was an instant connection:

“I think it’s safe to say they definitely struck up a clear rapport, bonding over their kids.”

The meeting of two of the most famous couples in the world — royalty and music royalty — drew massive attention in entertainment news, parenting media, and royal family updates.

#18 Allison Janney Called Kate Middleton “Honey”

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At the 2018 BAFTA Awards in London, Academy Award winner Allison Janney had a funny and slightly awkward moment with Prince William and Kate Middleton, the Prince and Princess of Wales.

The I, Tonya star had just won Best Supporting Actress and was barefoot when she met the royal couple. She had removed her heels for comfort by the end of the ceremony.

Sharing the story later, Allison said:

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“I just told her I was in bare feet and [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 etiquette.”

The candid interaction became a standout celebrity-royal moment, mixing Hollywood charm with the formal world of royal appearances, and quickly made headlines in entertainment news, award show highlights, and royal protocol discussions.

#19 Serena Williams And Kate Middleton

The Princess of Wales, Kate Middleton, met 23-time Grand Slam champion Serena Williams for the first time in 2016. The meeting sparked a warm connection between British royalty and one of the most celebrated athletes in the world.

Serena, who is known to be close friends with Meghan Markle, later included Kate in her list of top “bada women” alongside Beyoncé and Rihanna.

In a 2018 interview, Serena explained why Kate earned the No. 1 spot:

“Kate Middleton. And why’s that? Because of the woman’s ability to stand, composed in front of a bank of photographers after each of her births. So she’s officially No. 1.”

This powerful compliment from a global sports icon became a highlight in celebrity-royal friendships, showcasing Kate Middleton as a role model for women’s strength, post-pregnancy confidence, and grace under pressure.