Behind the scenes of Diana and Michael Jackson’s connection

A memorable photograph of Princess Diana and Michael Jackson has always resonated with me.

At first glance, it appears to be a simple moment shared between two iconic figures, yet a closer examination reveals a deeper narrative. Were you aware that their connection extended beyond mere appearances?

Both Princess Diana and Michael Jackson are figures whose legacies require no further elaboration; their fame is universally acknowledged.

While it was certainly plausible for these two extraordinary individuals to cross paths, few could have anticipated that their brief encounter would evolve into something beyond mere courteous exchanges.

They met in person only once. To begin with, Diana, affectionately referred to as “The People’s Princess,” was an avid music enthusiast. Reports indicate that her favorite band was Duran Duran, and she particularly enjoyed their music during the 1980s.

Moreover, her music collection included albums by Michael Jackson, indicating her appreciation for his artistry as well. It is said that she frequently played his albums, Thriller and Bad.

On the day of their meeting, she and her then-husband, Prince Charles, attended Michael Jackson’s concert during the Bad tour at Wembley Stadium, which marked both their initial and final encounter.

“She told me she was honored to meet me,” Jackson recounted in a 1997 interview with Barbara Walters.

Michael expressed that he felt an overwhelming sense of nervousness before greeting Diana—a palpable tension that can be sensed in the photographs from that day. The awkwardness of their first meeting can be attributed to a specific decision made by the superstar.

He chose to exclude the song “Dirty Diana” from the concert setlist, concerned that it might offend her. The song, which addresses the theme of a rock groupie, seemed inappropriate to perform in the presence of a royal, or so he believed.

“I took it out of the show in honor of Her Royal Highness,” Jackson stated during his interview with Barbara Walters in 1997.

Diana’s response to meeting Michael Jackson was noteworthy.
The decision did not resonate well with Diana.

Diana inquired of Michael whether he intended to perform “Dirty Diana” during the meet-and-greet prior to the concert. He informed her that he had excluded it from the setlist due to her presence. Nevertheless, she urged him to proceed with the performance, encouraging him to sing the song. In the end, Michael did indeed perform it.

Michael Jackson clearly admired Diana and held her in high regard.

“I thought the princess was just wonderful,” Jackson remarked to reporters 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 there romantic affection between Michael Jackson and Diana?
What many may not have expected was that their initial meeting in 1988 would spark 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 would usually call me late at night… often after three in the morning! And then she would keep me on the phone for hours. She primarily spoke about her children and the media.”

Michael asserted that Diana would engage him in lengthy conversations.

“Lisa Marie would become so jealous that she would go into another room to pick up the receiver and listen in,” he noted.

The authenticity of these late-night calls remains uncertain. According to Diana’s friends 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 shared similar experiences and a commitment to the same causes.
Both Diana and Michael Jackson were profoundly committed to philanthropic endeavors. Upon their initial meeting, the humanitarian 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 couple also exhibited a mutual appreciation for jewelry, as both were patrons of Butler & Wilson, one of England’s premier fashion jewelers.

However, was there a connection that transcended mere friendship and shared ideals?

Matt Fiddes, Jackson’s former bodyguard, corroborated the existence of late-night conversations, even asserting that the singer harbored romantic feelings for Diana.

Fiddes, who collaborated closely with Jackson for a decade, remarked:

“[Jackson] believed she was the only individual who could truly comprehend his life, particularly regarding the inability to go anywhere and the overwhelming media scrutiny… The invasion of privacy, the lack of personal space, and the relentless pursuit of his children.”

What was Michael Jackson’s response to Diana’s untimely death?

Another commonality between Michael Jackson and Princess Diana was their shared struggle with paparazzi. Both were among the most photographed figures for an extended period.

Diana was perpetually in the limelight, and her distinct persona, which often contrasted with the royal family, attracted significant attention from tabloids and photographers. Similarly, Michael Jackson’s life narrative and ever-evolving appearance made him a frequent target for the media.

It is reported that the two maintained their friendship until Diana’s tragic passing in 1997. Upon learning of her death, Michael was profoundly affected. According to The Express, the news impacted him so severely that he fainted and required revival with smelling salts after receiving the news.

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 so overwhelmed by Diana’s death that he was unable to take the stage.
In a poignant turn of events, Diana passed away merely two days following Michael’s 39th birthday.

Upon returning to the stage after a brief hiatus, he honored his departed 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 attend Diana’s funeral?
Michael did not participate in Diana’s funeral. Instead, he attended a memorial service held 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.”

Clad in black, adorned with a black fedora and a red armband, Jackson arrived at the Los Angeles church accompanied by a group of bodyguards. He was among the 1,000 guests present.

Michael Jackson frequently spoke warmly of Diana 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 shared a common experience with the press. I don’t believe anyone was pursued more than she and I were. We had a relationship where we would call each other late at night… just to cry on each other’s shoulders about how challenging and cruel the tabloids could be.”
It is indeed captivating to observe the moments shared between Diana and Michael Jackson. Regrettably, both departed prematurely under unusual circumstances. The photographer who captured that iconic moment likely did not foresee the historical significance of what would become Diana and Michael’s only encounter. In retrospect, the image symbolizes the initial tentative steps of a connection that would deepen over time.