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 upon closer examination, there is a wealth of depth to their narrative.
Were you aware that their connection encompassed more than what is immediately apparent?
Both Princess Diana and Michael Jackson require no additional 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, Diana, affectionately referred to as “The People’s Princess,” was an avid music enthusiast. In fact, her favorite band was reportedly Duran Duran, and she had a particular fondness for their music, especially 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 played the albums Thriller and Bad repeatedly.
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
But the move didn’t sit so well with Diana.
Diana inquired of Michael whether he intended to perform “Dirty Diana” during the meet-and-greet prior to the show. He responded that he had excluded it from the setlist due to her presence. Nevertheless, she urged him to sing it, encouraging him to proceed with the performance. In the end, Michael did perform the song.
Michael Jackson was evidently a great admirer of Diana and held her in high regard.
“I thought the princess was just wonderful,” Jackson expressed 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.
Did Michael Jackson have romantic feelings for 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 would often wake me up late at night… usually 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 keep him engaged on the phone for extended periods.
“Lisa Marie would become so jealous that she would retreat to another room, pick up the receiver, and eavesdrop,” he remarked.
Whether these late-night conversations actually took place 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.
But what we do know is that the two shared similar experiences and a passion for the same 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 couple 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, validated 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 respond to Diana’s demise?
What also connected Michael Jackson and Princess Diana was their common experience with paparazzi. Both were likely among the most photographed personalities for an extended period.
Diana was perpetually in the limelight, and her image, which contrasted with the royal family, consistently attracted the attention of tabloids and photographers. Likewise, Michael Jackson’s life narrative and ever-evolving appearance rendered him a prime target for the media.
The duo is reported to have maintained their friendship until Diana’s untimely death in 1997.
When Michael received the news of her passing, he was heartbroken. According to The Express, the news reportedly affected the star so profoundly that he fainted and required revival with smelling salts upon learning of her death.
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, but the organizers indicated that Jackson was so shaken by Diana’s death that he was unable to take the stage.
In a sad twist of fate, Diana had died just two days after Michael’s 39th birthday.
When he returned to the stage after a couple of days, he paid tribute to his late friend. He expressed, “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, referring to her as “one of the sweetest people I’ve ever known, because we could relate to each other.”
He added, “We had something in common, with the press. I don’t believe anyone was pursued more than she and I were. We shared a bond, where we would call each other late at night… just to cry on each other’s shoulders about how challenging and cruel the tabloids can be.”
It’s quite fascinating to watch Diana and Michael Jackson together. Sadly, they’re both gone before their time under strange circumstances. The photographer capturing that iconic moment likely didn’t realize the historic significance of what would be Diana and Michael’s only meeting. Yet, in hindsight, the image reflects the first tentative steps of a bond that would grow stronger with time.
