The remarkable image of Princess Diana and Michael Jackson has always stuck in my mind.
At first glance, it appears to be just a shared moment between these two legends, but upon closer inspection, we realize their story runs much deeper.
Did you know their relationship goes much deeper than it seems?
Both Princess Diana and Michael Jackson are iconic figures whose fame speaks for itself.
While it was no surprise that these two personalities met, few would have imagined that their encounter could lead to more than a casual conversation…
In fact, they only met in person once.
Initially, Diana, known as the «People’s Princess,» was a huge music lover. Her favorite band was Duran Duran, and she loved their songs, especially from the 1980s.
However, her record collection also included Michael Jackson albums, proving that she enjoyed his music. It is said that she played «Thriller» and «Bad» over and over again.
Michael Jackson’s music was the real reason Diana met him for the first time on July 16, 1988.
That day, she and her then-husband, Prince Charles, attended Michael Jackson’s «Bad» tour concert at Wembley Stadium—an encounter that would be both her first and last.
«He told me it was an honor to meet me,» Jackson recalled in a 1997 interview with Barbara Walters.
Michael admitted to being very nervous before shaking Diana’s hand—a tension that is evident in photos from that day. Because of this, their first meeting was somewhat awkward and reserved.
One reason for the tension was that the superstar had decided to remove the song «Dirty Diana» from the concert setlist, fearing it might upset the princess. The song, about a rock groupie, seemed unsuitable to be performed in front of the royal family, or so he thought.
«I removed it from the concert in honor of Her Royal Highness,» Jackson explained to Barbara Walters in 1997.
Diana’s Reaction to Meeting Michael Jackson
Diana, however, did not like Michael’s decision.
At their pre-concert meeting, Diana asked Michael if he would sing «Dirty Diana.» He explained that he had removed it from the setlist because of her presence. Despite this, Diana insisted that he sing it and encouraged him to do so. Eventually, Michael agreed and sang it.
Michael Jackson was a great admirer of Diana and respected her deeply.
«I thought the princess was incredible,» Jackson told the press.
Knowing how much Diana adored her sons, he decided to give her two miniature tour jackets for Prince William and Prince Harry.
Diana, a huge pop music fan, reportedly danced continuously throughout the entire concert, while Prince Charles remained seated.
Was Michael Jackson in love with Diana?
Few would have predicted that their first meeting in 1988 would mark the beginning of a surprisingly close bond.
«We were very close,» Jackson told German media in 1999. «She was very close to me on the phone… I was still married to Lisa Marie [Presley]. Diana would usually wake me up late at night… usually after 3 a.m.! And then she would hug me for hours on the phone. She talked mostly about her children and the press.»
Michael said Diana kept him on the phone for hours.
«Lisa Marie was so jealous that she would go into the other room, pick up the receiver, and listen,» he added.
Although it was never confirmed whether these late-night calls actually took place, some of Diana’s close friends who spoke to The Express claim that Jackson never had her home number. If he tried to reach her, Kensington Palace staff were instructed not to contact him.
What is certain is that they had similar experiences and pursued the same goals.
Both Diana and Michael Jackson shared a deep commitment to social causes. When they met, Jackson, a humanitarian, had already donated $188,000 to the Prince’s Trust, a youth charity, and another $126,000 to the children’s charity of London’s Great Ormond Street Hospital.
The couple also had similar tastes in jewelry and were regular customers at Butler & Wilson, one of England’s most exclusive jewelers.
Was there more than just friendship and shared values between them?
Jackson’s former bodyguard, Matt Fiddes, confirmed the late-night phone calls and suggested that the singer was «in love» with Diana.
Fiddes, who worked with Jackson for ten years, noted:
«[Jackson] felt like he was the only person in the world who could understand his life—given the fact that he couldn’t go anywhere, given the uncontrollable media coverage… the intrusions into his personal life, the lack of privacy, the bullying of children.»
How did Michael Jackson react to Diana’s death? One of the experiences that Michael Jackson and Princess Diana shared was the constant attention of the paparazzi. For years, both were among the most photographed people in the world.
Constantly in the spotlight, Diana stood out for her personality, which contrasted with the royal family and constantly attracted the attention of the tabloids and photographers. Likewise, Michael Jackson’s constantly changing life and appearance made him a major media target.
The two reportedly maintained their friendship until Diana’s tragic death in 1997.
When Michael learned of her death, he was deeply saddened. According to The Express, the news was so shocking that he fainted and had to be resuscitated with smelling salts.
The singer also decided to postpone a planned performance on his HIStory tour. Michael was scheduled to perform in Belgium in front of 60,000 people, but organizers said Jackson was so shaken by Diana’s death that he couldn’t take the stage.
Tragically, Diana died just two days after Michael’s 39th birthday.
When he finally returned to the stage a few days later, he paid a moving tribute to his friend. With a heavy heart, he said, «I said in my heart, ‘I love you, Diana. Shine on. And shine forever, for you are truly the people’s princess.'»
Did Michael Jackson attend Diana’s funeral?
Although Michael Jackson did not attend Diana’s funeral, he did attend a memorial service in Los Angeles. During the event, he told reporters he wanted to be there to «honor my friend who is no longer here… I love her.»
Dressed in black and wearing a black hat, Jackson arrived at a Los Angeles church surrounded by a procession of bodyguards. He was one of 1,000 guests in attendance.
Michael Jackson expressed his admiration for Diana several times after her death, fondly recalling in 2003: «She was one of the kindest people I’ve ever met because we could relate to her.» He continued: «We had some dealings with the press. I don’t think they ever bothered anyone except her and me. And we had a relationship where we would call each other late at night… and just cry on each other’s shoulders because the tabloids could be so difficult and complicated.»
It’s fascinating to see Diana and Michael Jackson together. Sadly, the two parted ways far too soon and under tragic circumstances. The photographer who captured this iconic moment likely wasn’t aware of the historical significance of what was supposedly the only meeting between Diana and Michael. Looking back, however, the image reflects the cautious first steps of a bond that grew stronger over time.
