There’s a famous picture of Princess Diana and Michael Jackson that has always stuck with me. At first glance, it might seem like just a snapshot of two legendary figures meeting, but there’s so much more beneath the surface of their story.
Did you know their bond ran deeper than what you see on the surface? Both Princess Diana and Michael Jackson are cultural icons, so it’s not surprising that they eventually crossed paths. However, few could have ever imagined that this encounter would lead to something special beyond just small talk!
Their Only Meeting
To kick things off, Diana—lovingly called “The People’s Princess”—was a massive music fan. Her favorite band was Duran Duran, and she played their songs on repeat during the 1980s. But guess what? She was also a big fan of Michael Jackson! In fact, she loved his albums Thriller and Bad, which were among her favorites.
Their paths finally crossed on July 16, 1988, when Diana and her husband, Prince Charles, attended Michael’s concert during his Bad tour at Wembley Stadium. This would mark both their first and only meeting. Michael later told Barbara Walters in a 1997 interview, “She told me she was honored to meet me.”
The moment was electrifying, but a bit awkward too. Michael was super nervous about meeting Diana. Can you imagine? To top it off, he made a decision to remove his song “Dirty Diana” from the concert playlist because he thought it might upset her. “I took it out of the show in honor of Her Royal Highness,” he explained during the same interview.
Diana’s Response
However, Diana wasn’t bothered by it at all! In fact, she asked Michael at the meet-and-greet if he was going to perform “Dirty Diana.” When he told her he took it out for her sake, she insisted he go ahead and sing it anyway. And guess what? Michael ended up performing the song!
Michael held Diana in high regard. “I thought the princess was just wonderful,” he shared with reporters. As a thoughtful gift, he even presented Diana with two tiny tour jackets for her sons, Princes William and Harry.
During the concert itself, Diana was reported to be dancing the whole time, while Prince Charles stayed seated, a little less enthusiastic. It seems like her love for music truly shone through!
A Deeper Bond
What many people didn’t see coming was that their quick meeting in 1988 sparked a powerful connection between them. “We were very close,” Michael revealed in a 1999 German interview. “She was extremely close by phone… I was still married to Lisa Marie [Presley].
Diana woke me up usually late at night…mostly after three in the morning! And then she held me for hours on the telephone. She talked mostly about her children, and the press.”
Michael claimed that these late-night conversations were frequent, but whether they really happened remains a bit of a mystery. Diana’s friends mentioned to The Express that Michael didn’t even have Diana’s private number—if he called Kensington Palace, they were instructed not to connect him to her.
But one thing is clear: both Diana and Michael were passionate about helping others. When they first met, Michael had already donated $188,000 to the Prince’s Trust charity and another $126,000 to Great Ormond Street Hospital. They both also shared a love for dazzling jewelry from a famous fashion jeweler, Butler & Wilson.
Was there something more intense than just friendship between them? Michael’s former bodyguard, Matt Fiddes, thinks so. He even claimed that Michael was “in love” with Diana. Fiddes explained, “He felt she was the only person in the world who could understand his life in terms of not being able to go anywhere, and the media stories that got out of hand…
The intrusion into the private life, having no privacy whatsoever, the children being hounded.”
Tragic Loss
But what they truly bonded over was their shared struggles with the media. Diana was constantly under the watchful eye of the paparazzi, and the media obsession with her life was relentless. Similarly, Michael’s life, filled with fame and controversy, made him a constant target as well.
Diana and Michael remained friends until the day of her tragic passing in 1997. When Michael received the heartbreaking news, he was completely devastated.
According to The Express, the news hit him so hard that he fainted and needed smelling salts to revive himself. He even postponed a concert in Belgium for 60,000 fans, unable to perform that night due to his shock over losing Diana.
In a cruel twist of fate, Diana passed away just two days after Michael’s 39th birthday. When he returned to the stage days later, he paid tribute to her, stating, “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, because you are the true princess of the people.’”
Remembering Diana
Although Michael didn’t make it to Diana’s funeral, he attended a memorial service for her in Los Angeles. Dressed in black with a fedora and red armband, he arrived with his bodyguards, wanting to pay homage to his dear friend. He told reporters, “I wanted to honor my friend who is no longer here… I love her.”
Michael spoke fondly of Diana numerous times after her death. In 2003, he called her “one of the sweetest people I’ve ever known.” He added, “We shared something in common, with the press. I don’t think they hounded anyone more than her and myself.
And we had a relationship where we would call each other late at night… just cry on each other’s shoulders about how hard and difficult and how mean the tabloids can be.”
It’s so fascinating to see Diana and Michael’s connection. It’s tragic that they are both gone, taken before their time in such strange circumstances. When that photographer captured their iconic moment, they probably had no idea how historically significant that meeting would become.
Looking back, the photo shows the beginning of a special bond that would only grow stronger through shared experiences and understanding.
So, what do you think of this amazing story? Share your thoughts in the comments below! It’s incredible how two superstars connected and supported each other.
