At first glance, this appears to be just a moment captured between two legends. But if you look closer, their story turns out to be much more interesting.
Did you know their connection was deeper than it seemed at first?
Neither Princess Diana nor Michael Jackson needs an introduction—their iconic status speaks for itself.
It’s no surprise that these two incredible individuals met one day. But few could have predicted that their encounter would lead to something more than just a polite conversation…
They met in person only once.
First of all, Princess Diana, known as the “People’s Princess,” was a big fan of music. Her favorite band, reportedly, was Duran Duran—she loved their songs in the 1980s. However, her record collection also included albums by Michael Jackson, showing her admiration for his music. It is said that she would often listen to “Thriller” and “Bad” on repeat.
Michael Jackson’s music was the reason for their only meeting on July 16, 1988.
That day, she and her then-husband, Prince Charles, attended a concert of the Bad Tour at Wembley Stadium. This was their first and only personal encounter.
“She told me it was an honor to meet me,” Jackson recalled in a 1997 interview with Barbara Walters.
Michael remembered feeling incredible nervousness before shaking Diana’s hand—a tension that can even be felt in the photos from that day.
There was a reason their first meeting felt a bit awkward and cautious.
He removed the song “Dirty Diana” from the concert.
The reason was that Michael had decided to exclude “Dirty Diana” from the setlist, fearing it might offend the princess. The song, about a rock groupie, seemed inappropriate to perform in the presence of a royal.
“I took it out of the show in honor of Her Highness,” Michael told Barbara Walters in 1997.
Diana’s reaction to the meeting with Michael.
However, this gesture did not sit well with the princess.
During the meeting before the concert, Diana asked Michael if he was going to perform “Dirty Diana.” When he explained that he had removed it because of her presence, she insisted that he include it and perform it. In the end, Michael followed her request and added the song back to the setlist.
Jackson clearly admired Diana and treated her with great respect.
“I thought the princess was just amazing,” he confessed to reporters.
Knowing how much she adored her children, Michael gave Diana two miniature concert jackets for Princes William and Harry.
Diana, a passionate fan of pop music, reportedly danced throughout the concert, while Prince Charles remained seated.
Was Michael Jackson in love with Diana?
Few expected that their first meeting in 1988 would lead to such a strong emotional connection.
“We were very close,” Jackson told German media in 1999. “She often called me… I was still married to Lisa Marie [Presley] at the time. Diana would usually wake me up late at night… mostly after 3 a.m.! And then she would keep me on the phone for hours. She mostly talked about her children and the press.”
Michael claimed that Diana could talk to him for hours on the phone.
“Lisa Marie was terribly jealous. She would go to another room, pick up the phone, and eavesdrop,” he added.
However, it’s impossible to confirm whether these late-night calls actually took place. According to Diana’s friends, who spoke to The Express, Jackson supposedly never had her personal phone number. If he called Kensington Palace, the staff were instructed not to connect him with the princess.
What is certain is that both of them went through similar struggles and shared a passion for the same charitable causes.
Both were dedicated to charity.
Diana and Michael Jackson were both very active in charity work. By the time of their first meeting, Jackson, known for his humanitarian efforts, had already donated $188,000 to the Prince’s Trust, a youth charity, as well as $126,000 to the children’s fund at Great Ormond Street Hospital in London.
Additionally, they shared a taste for jewelry. Both were clients of the renowned British jeweler Butler & Wilson.
But was there something more between them than just friendship and shared values?
Was Michael Jackson in love with Princess Diana?
Michael Jackson’s former bodyguard, Matt Fiddes, claimed that the late-night phone calls were real and even suggested that the singer was “in love” with Diana.
Fiddes, who worked with Jackson for ten years, said:
“[Michael] felt that she was the only person in the world who could understand his life: the inability to go outside, the scandalous rumors in the press… Constant invasion of privacy, no privacy, the persecution of children…”
How did Michael Jackson react to Diana’s death?
Diana and Michael shared another connection—the paparazzi. For many years, they were two of the most photographed people in the world.
Diana was constantly in the spotlight, and her controversial image within the royal family inevitably attracted tabloid and reporter attention. Similarly, Michael Jackson, with his changing appearance and eccentric lifestyle, was an easy target for the media.
It’s said their friendship lasted until Diana’s tragic death in 1997.
When Michael heard about her death, he was devastated. According to The Express, the news shocked him so much that he passed out and had to be revived with smelling salts.
He also postponed a concert during his HIStory tour. Jackson was scheduled to perform in front of 60,000 fans in Belgium, but the organizers announced that the singer was so heartbroken that he could not go on stage.
Ironically, Diana passed away just two days after Michael’s 39th birthday.
Farewell to the Princess
A few days after the tragedy, Michael returned to the stage and dedicated the concert to Diana’s memory.
He said, “In my heart, I said, ‘I love you, Diana. Shine. And shine forever, because you are the true people’s princess.’”
However, Michael did not attend Diana’s funeral in London. Instead, he attended a memorial service in Los Angeles, where he told reporters:
“I came to honor the memory of my friend who is no longer here… I love her.”
Dressed in a black suit, black fedora, and a red armband, Jackson arrived at the church surrounded by bodyguards. He was one of thousands of guests at the service.
Michael Jackson on Diana after her death
Years later, Jackson frequently spoke fondly of Diana.
In 2003, he spoke about her again:
“She was one of the nicest people I ever knew because we understood each other.”
“We shared one common problem—the press. I don’t think anyone was hounded as much as she and I were. We had a special relationship: we would call each other at night… Just complain, cry to each other about how hard it was, how cruel the tabloids could be.”
These words clearly show that Diana and Michael Jackson were connected by more than just fame. They found support in each other in dealing with the media attention that often turned into full-blown harassment.
It’s fascinating to observe moments where Princess Diana and Michael Jackson are together. Unfortunately, both of them left us too soon and under strange circumstances. The photographer who captured this iconic moment likely didn’t realize the historical significance of what would become the only meeting between Diana and Michael.
But looking back, this photo symbolizes the first tentative steps of a bond that only grew stronger over time.