An unforgettable photo of Princess Diana and Michael Jackson has always stayed with me.
At first, it may appear to be just a simple moment between two famous figures, but if you look closer, there’s a deeper story behind their connection. Did you realize their bond was far more meaningful than it initially seems?
Both Princess Diana and Michael Jackson are legends in their own right, with iconic legacies that need no explanation. While it was no surprise that these two larger-than-life stars would eventually meet, few could have predicted that their interaction would evolve into something much more significant than just casual conversation.
Only met in person once
To start, Diana, fondly known as “The People’s Princess,” was an avid music lover. She had a particular fondness for the band Duran Duran, whose music she enjoyed throughout the 1980s.
But Diana’s record collection wasn’t just limited to their albums; it also included works by Michael Jackson, proving she was a fan of his music as well. She was known to play his iconic albums Thriller and Bad on repeat. It was Michael’s music that led to their fateful meeting on July 16, 1988.
On that day, Diana and her husband, Prince Charles, attended Michael Jackson’s Bad tour concert at Wembley Stadium, which would be the only time they would meet in person.
“She told me she was honored to meet me,” Jackson shared with Barbara Walters during a 1997 interview.
Michael admitted feeling quite nervous before greeting Diana, and you can almost sense that unease in the photos from the meeting. The reason for the tension? Jackson had decided to remove the song “Dirty Diana” from the concert setlist, worried it might offend the princess. The track, which addresses a rock groupie, seemed like an awkward choice with a female royal in the audience, or so he thought.
“I took it out of the show in honor of Her Royal Highness,” Jackson explained in the 1997 interview.
Diana’s reaction to meeting Michael Jackson was one of true admiration
But Diana didn’t quite agree with Michael’s decision. before the show, Diana asked Michael if he was still planning to perform “Dirty Diana” during the meet-and-greet. Michael explained that he had taken it out of the setlist out of respect for her, but she insisted he perform it, urging him to go ahead with the song. In the end, Michael performed it as she requested. It was clear that Michael held Diana in high regard and admired her greatly.
“I thought the princess was just wonderful,” Jackson shared with reporters at the time.
Understanding her love for her sons, Michael also gave Diana two miniature tour jackets for Princes William and Harry. As an enthusiastic fan of pop music, Diana was said to have danced throughout the entire concert, while Prince Charles chose to remain seated.
Did Michael Jackson have romantic feelings for Diana?
What many didn’t expect was that their first meeting in 1988 would spark a powerful and lasting connection.
“We were very close,” Jackson shared with German media in 1999. “She was extremely close by phone… I was still married to Lisa Marie [Presley]. Diana would call me late at night… usually after three in the morning! She’d keep me on the phone for hours, mostly talking about her children and the press.”
Michael claimed that Diana would talk to him for extended hours during those late-night calls.
“Lisa Marie would get so jealous, she’d go into another room, pick up the phone, and listen in,” he added.
However, whether these late-night calls actually took place is uncertain. Diana’s friends, in a conversation with The Express, noted that Michael likely never had Diana’s personal number. If he called Kensington Palace, staff were reportedly instructed not to connect him to her. What is clear, though, is that both shared similar experiences and a passion for the same causes.
Both Diana and Michael Jackson were deeply committed to humanitarian causes. At the time of their first meeting, Jackson had already donated $188,000 to the Prince’s Trust charity, which supports youth initiatives, and another $126,000 to the children’s charity at London’s Great Ormond Street Hospital.
They also shared a similar taste in jewelry, both being clients of one of England’s top fashion jewelers, Butler & Wilson. But was their connection more than just friendship and shared values?
Matt Fiddes, Jackson’s former bodyguard, supported the idea of the late-night calls, even suggesting that Michael was “in love” with Diana. Fiddes, who worked closely with Jackson for over a decade, revealed:
“[Jackson] felt she was the only person who truly understood his life, with the constant media scrutiny, the lack of privacy, and the way his personal life was constantly invaded. She was the one person who could relate to the pressure of it all, especially regarding his children being hounded by the press.”
How did Michael Jackson react to Diana’s death?
What also brought Michael Jackson and Princess Diana together was their shared experience with the paparazzi. Both were among the most photographed individuals of their time.
Diana was perpetually in the public eye, with her distinctive persona and strained relationship with the royal family sparking constant media attention. Similarly, Michael Jackson’s life and ever-evolving appearance made him a frequent target for photographers and tabloids.
The two remained friends until Diana’s tragic death in 1997. When Michael heard of her passing, he was deeply affected. Reports from The Express revealed that the news hit him so hard that he fainted and had to be revived with smelling salts.
He also postponed a performance on his HIStory tour. Jackson was scheduled to perform in Belgium in front of 60,000 fans, but the organizers stated that he was so shaken by Diana’s death that he couldn’t bring himself to perform.
In a poignant twist of fate, Diana passed away just two days after Michael’s 39th birthday.
When he finally returned to the stage, he honored his late friend with a tribute. He told the audience, “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, because you are the true princess of the people.’”
Did Michael Jackson go to Diana’s funeral?
Michael Jackson did not attend Princess Diana’s funeral, but he did attend a memorial service for her in Los Angeles. There, he explained to reporters that he wanted to be present to “honor my friend who is no longer here… I love her.”
Dressed in black, with a black fedora and a red armband, Jackson arrived at the church surrounded by his bodyguard entourage. He was one of 1,000 guests paying their respects.
In the years following Diana’s death, Michael spoke about her with deep fondness. In 2003, he described her as “one of the sweetest people I’ve ever known, because we could relate to each other.”
He went on to say, “We shared something in common with the press. I don’t think anyone was hounded more than her and me. And we had a relationship where we would call each other late at night… just cry on each other’s shoulders about how hard it was, how difficult it was, and how mean the tabloids could be.”
It’s truly fascinating to reflect on the rare moments shared between Diana and Michael Jackson. Tragically, both left us far too soon, and under unusual circumstances. The photographer who captured that iconic image probably didn’t realize the historical significance of what was about to unfold—Diana and Michael’s only meeting. Yet, looking back, the photo symbolizes the beginning of a connection that would only deepen with time.