A memorable photograph of Princess Diana and Michael Jackson has always resonated with me.
On the surface, it appears to be merely a fleeting encounter between two iconic figures; however, upon closer examination, one can uncover a richer narrative behind their connection.
Are you aware that their relationship encompassed more than what is immediately apparent?
Both Princess Diana and Michael Jackson are figures whose legendary status requires no additional introduction.
It was indeed plausible for these two remarkable individuals to encounter one another; however, few could have foreseen that their interaction would develop into something more substantial than a simple exchange of pleasantries.
Only met in person once
To begin with, Diana, affectionately known as ”The People’s Princess,” was a big music fan. In fact, her favorite band was reportedly Duran Duran, and she loved their music, especially during the 1980s.
However, Diana’s record collection also featured albums by Michael Jackson, which shows that she truly enjoyed his music as well. For example, she is said to have played the albums Thriller and Bad on repeat.
MJ’s music served as the catalyst for Diana’s encounter with him on July 16, 1988. On that occasion, she and her then-husband, Prince Charles, were present at Michael Jackson’s Bad tour concert held at Wembley Stadium, which would be both their inaugural and final meeting.
Jackson recounted to Barbara Walters during a 1997 interview, “She expressed that she was honored to meet me.”
Michael remembered experiencing significant anxiety prior to greeting Diana—a feeling that is almost palpable in the photographs taken that day. The initial meeting had an air of awkwardness and hesitation for a specific reason.
This discomfort stemmed primarily from the fact that the renowned artist had chosen to exclude the song “Dirty Diana” from the concert setlist, concerned that it might offend her. The track, which narrates the story of a rock groupie, seemed unsuitable 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 told Barbara Walters in 1997.
Diana’s reaction to meeting Michael Jackson
But the move didn’t sit so well with Diana.
Diana asked Michael if he was going to perform “Dirty Diana” during the meet-and-greet before the show. He replied that he had removed it from the setlist because of her presence. However, she insisted that he perform it, encouraging him to go ahead and sing the song. Ultimately, Michael performed the song.
Michael Jackson was clearly a big fan of Diana and held a great deal of respect for her.
”I thought the princess was just wonderful,” Jackson told reporters at the time.
Knowing how much she adored her sons, Michael also gifted her two miniature tour jackets for her children, Princes William and Harry.
Diana, an avid pop music fan, was said to have danced during the whole concert while Prince Charles remained seated.
Was Michael Jackson in love with Diana?
What many may not have foreseen 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 always just a phone call away… At that time, I was still married to Lisa Marie [Presley]. Diana would often wake me up late at night… usually after three in the morning! She would then keep me on the line for hours. Our conversations primarily revolved around her children and the media.”
Michael asserted that Diana would engage him in lengthy phone conversations.
“Lisa Marie would become so envious that she would retreat to another room, pick up the receiver, and eavesdrop,” he noted.
The authenticity of these late-night calls remains unverified. According to friends of Diana who spoke to The Express, Jackson allegedly did not possess Diana’s private number. If he attempted to call Kensington Palace, the staff were instructed not to connect him to the princess.
However, it is evident that both individuals shared similar life experiences and a mutual dedication to the same causes.
Both Diana and MJ were profoundly committed to civic initiatives. Upon their initial meeting, the philanthropic Jackson had contributed $188,000 to the youth-focused Prince’s Trust charity, along with an additional $126,000 to the children’s charity at Great Ormond Street Hospital in London.
The pair also exhibited a mutual appreciation for jewelry, as both Michael and Diana were patrons of Butler & Wilson, one of England’s premier fashion jewelers.
However, was there a deeper connection beyond mere friendship and shared ideals?
Jackson’s former bodyguard, Matt Fiddes, corroborated the existence of late-night conversations, even asserting that the singer was “in love” with Diana.
Fiddes, who collaborated closely with Jackson for a decade, remarked:
“[Jackson] believed she was the only individual who could comprehend his life, particularly regarding his inability to go anywhere and the overwhelming media scrutiny… 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?
Michael Jackson and Princess Diana were united by their common experiences with the paparazzi, as both were among the most photographed figures for an extended period.
Diana’s life was perpetually under public scrutiny, and her distinct persona, which often contrasted with that of the royal family, attracted significant attention from tabloids and photographers. In a similar vein, Michael Jackson’s intriguing life narrative and evolving appearance made him a frequent target for media coverage.
It is reported that the two maintained a friendship until Diana’s untimely death in 1997.
Upon learning of her passing, Michael was profoundly affected. According to The Express, the news impacted him so severely that he fainted and required revival with smelling salts.
He also chose to postpone a performance on his HIStory tour. Scheduled to perform in Belgium before an audience of 60,000, the organizers indicated that Jackson was too shaken by Diana’s death to take the stage.
In a poignant coincidence, Diana passed away just two days following Michael’s 39th birthday.
When he eventually returned to perform a few days later, he honored his late friend with a heartfelt tribute, 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.’”
Did Michael Jackson go to Diana’s funeral?
Michael did not participate in Diana’s funeral; instead, he attended a memorial service held in Los Angeles. During this event, he expressed to reporters his desire to be present to “honor my friend who is no longer here… I love her.”
Clad in black attire, complete 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.
Following Diana’s passing, Michael Jackson frequently spoke warmly of her. 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, stating, “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, how hard and difficult and how mean the tabloids can be.”
Observing the interaction between Diana and Michael Jackson is truly captivating. Regrettably, both individuals departed from this world prematurely and under unusual circumstances. The photographer who captured that memorable moment may not have fully comprehended the historical importance of what would become the sole encounter between Diana and Michael. However, in retrospect, the photograph symbolizes the initial, tentative stages of a relationship that would deepen over time.
