There exists a memorable image of Princess Diana and Michael Jackson that has always remained in my mind.
Upon initial observation, it appears to be merely a moment shared between two icons, yet a closer examination reveals a much richer narrative.
Were you aware that their connection encompassed more than what is immediately apparent?
Both Princess Diana and Michael Jackson require no further introduction – their legendary status is self-evident.
It was certainly not beyond imagination that these two extraordinary figures would cross paths, but few could have anticipated that their meeting would evolve into something beyond mere courteous conversation…
Only met in person once
To start with, Diana, affectionately referred to as “The People’s Princess,” was an avid music enthusiast. In fact, it has been reported that her favorite band was Duran Duran, and she particularly enjoyed their music during the 1980s.
Nevertheless, Diana’s record collection also included albums by Michael Jackson, indicating that she genuinely appreciated his music as well. For instance, it is said that she frequently played the albums Thriller and Bad on repeat.
Michael Jackson’s music was also the catalyst for Diana meeting him on July 16, 1988.
On that day, she and her then-husband, Prince Charles, attended Michael Jackson’s Bad tour concert at Wembley Stadium, which marked both their first and last encounter.
“She told me she was honored to meet me,” Jackson recounted to Barbara Walters in a 1997 interview.
Michael remembered feeling extremely nervous before shaking hands with Diana—a tension that is almost palpable in the photographs from that day. There was a reason their initial meeting felt somewhat awkward and tentative.
This was primarily because the superstar had chosen to exclude the song “Dirty Diana” from the concert setlist, concerned that it might offend her. The song, which revolves around a rock groupie, seemed inappropriate to perform in the presence of the female royal, or so he believed.
“I took it out of the show in honor of Her Royal Highness,” Jackson stated to Barbara Walters in 1997.
Diana’s reaction to meeting Michael Jackson
However, the decision did not resonate well with Diana.
Diana inquired of Michael whether he intended to sing “Dirty Diana” at the meet-and-greet prior to the performance. He responded that he had excluded it from the setlist due to her attendance. Nevertheless, she urged him to sing it, motivating him to proceed with the performance of the song. In the end, Michael did indeed perform the song.
Michael Jackson was evidently a great admirer of Diana and held her in high regard.
“I found the princess to be simply marvelous,” Jackson expressed to the media at that time.
Understanding her deep affection for her sons, Michael also presented her with two miniature tour jackets for her children, Princes William and Harry.
Diana, a passionate fan of pop music, was reported to have danced throughout the entire concert while Prince Charles remained seated.
Was Michael Jackson in love with Diana?
What many may not have expected was that their initial meeting in 1988 would spark the beginning of a remarkably strong connection.
“We were very close,” Jackson recounted to German media in 1999. “She was extremely close by phone… I was still married to Lisa Marie [Presley]. Diana typically woke me up late at night… mostly after three in the morning! And then she would hold me on the phone for hours. She primarily spoke about her children and the media.”
Michael asserted that Diana would keep him engaged on the phone for extended periods.
“Lisa Marie would often become so envious that she would retreat to another room, pick up the receiver, and eavesdrop,” he remarked.
The authenticity of these late-night conversations remains unverified. According to Diana’s acquaintances who spoke with The Express, Jackson allegedly never possessed Diana’s private number. If he attempted to call Kensington Palace, the staff were instructed not to connect him to the princess.
However, what is certain is that the two had shared experiences and a mutual enthusiasm for similar causes.
Both Diana and MJ were profoundly involved in civic initiatives. Upon their initial meeting, the humanitarian Jackson had contributed $188,000 to the youth-focused Prince’s Trust charity, along with an extra $126,000 to the children’s charity at London’s Great Ormond Street Hospital.
The pair also had a mutual appreciation for jewelry. Both Michael and Diana were patrons of one of England’s premier fashion jewelers, Butler & Wilson.
However, was there something more significant than mere friendship and shared principles?
Jackson’s former bodyguard, Matt Fiddes, verified the late-night communications, even asserting that the singer was “in love” with Diana.
Fiddes, who collaborated closely with Jackson for ten years, stated:
“[Jackson] believed she was the only individual in the world who could comprehend his life regarding the inability to go anywhere, and the media narratives that spiraled out of control… The invasion of his private life, the complete lack of privacy, and the relentless pursuit of his children.
How did Michael Jackson react to Diana’s death?
What also connected Michael Jackson and Princess Diana was their mutual experience with paparazzi. Both were likely among the most photographed individuals for many years.
Diana was perpetually in the limelight, and her persona, which contrasted with that of the royal family, consistently attracted the attention of tabloids and photographers alike. In a similar vein, Michael Jackson’s life narrative and ever-evolving appearance rendered him a prime target for the media.
The two are reported to have maintained their friendship until Diana’s tragic demise in 1997.
Upon learning of her death, Michael was heartbroken. According to The Express, the news reportedly affected the star so profoundly that he fainted and required revival with smelling salts after hearing of her passing.
He also delayed a performance on his HIStory tour. The singer was scheduled to perform a concert in Belgium before an audience of 60,000 people, but the organizers indicated that Jackson was so shocked by Diana’s death that he was unable to take the stage.
In a poignant twist of fate, Diana passed away just two days following Michael’s 39th birthday.
When he returned to the stage after a few days, he honored his late friend. He conveyed, “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?
However, Michael did not attend Diana’s funeral. Instead, he participated in a memorial service for her in Los Angeles, where he informed reporters of his desire 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 in Los Angeles accompanied by a group of bodyguards. He was among the 1,000 guests present.
Michael Jackson spoke warmly of Diana on multiple occasions following her passing. In 2003, he reiterated his sentiments, describing her as “one of the sweetest people I’ve ever known, because we could relate to each other.”
He elaborated, “We had something in common, with the press. I don’t believe anyone was pursued more than her and myself. We shared a relationship where we would call each other late at night… just cry on each other’s shoulders about how hard and difficult it was and how cruel the tabloids could be.”
It is quite intriguing to observe Diana and Michael Jackson together. Unfortunately, they both departed this world prematurely under unusual circumstances. The photographer who captured that iconic moment likely did not recognize the historical importance of what would be Diana and Michael’s only encounter. Yet, in retrospect, the image symbolizes the initial tentative steps of a connection that would deepen over time.
