Look Closely The photographer captured something strange in this picture and didn’t know how unique the photograph was until he checked it…check the first comment “
A striking image of Princess Diana and Michael Jackson has always resonated with me. At first glance, it seems like just a moment shared between two legends, but a deeper look reveals much more to their story. Was there more to their bond than met the eye?
Neither Princess Diana nor Michael Jackson needs introduction; their iconic status speaks for itself. While it was not unimaginable that these two larger-than-life personalities would meet, few could have guessed their encounter would lead to something more than polite small talk.
Diana, affectionately known as “The People’s Princess,” was a passionate music fan. Reportedly, her favorite band was Duran Duran, whose music she adored, especially during the 1980s. Her record collection also featured Michael Jackson’s albums, indicating her genuine enjoyment of his music. She is said to have played “Thriller” and “Bad” on repeat, for instance.
It was Jackson’s music that brought Diana to meet him on July 16, 1988. That day, she and her then-husband, Prince Charles, attended Michael Jackson’s ‘Bad’ tour concert at Wembley Stadium. This occasion marked both their first and last meeting.
“She told me she was honored to meet me,” Jackson told Barbara Walters in a 1997 interview. Michael recalled feeling incredibly nervous before shaking hands with Diana—a tension palpable in photos from that day. Their first encounter felt somewhat awkward and tentative for a specific reason. This was largely because the superstar had decided to remove the song “Dirty Diana” from the concert setlist, worried it might offend her. The song, which is about a rock groupie, seemed inappropriate to perform with the royal in attendance, or so he believed. “I took it out of the show in honor of Her Royal Highness,” Jackson told Barbara Walters in 1997.
However, the move didn’t sit well with Diana. During their pre-show meet-and-greet, Diana asked Michael if he would perform “Dirty Diana.” He explained that he had removed it from the setlist due to her presence, fearing it might be inappropriate. However, she insisted he perform it, encouraging him to go ahead with the song. Ultimately, Michael obliged.
Michael Jackson was clearly a great admirer of Diana, holding her in high regard. “I thought the princess was just wonderful,” Jackson told reporters at the time. Knowing her adoration for her sons, Michael also gifted her two miniature tour jackets for Princes William and Harry. Diana, an avid pop music fan, reportedly danced throughout the concert while Prince Charles remained seated.
What many might not have anticipated was that their first encounter in 1988 would ignite an incredibly powerful bond. “We were very close,” Jackson told German media in 1999. “She was extremely close by phone… I was still married to Lisa Marie [Presley]. Diana woke me up usually late at night… mostly after three in the morning! And then she held me for hours on the telephone. She talked mostly about her children, and the press.” “Lisa Marie used to get so jealous she would go into the other room, pick up the receiver, and listen in,” he said.
Whether these late-night calls truly happened, however, remains unconfirmed. According to Diana’s friends who spoke with The Express, Jackson reportedly never had Diana’s private number. Staff at Kensington Palace were instructed not to connect him to the princess if he called. What is known, however, is that the two shared similar experiences and a passion for the same causes.
Both Diana and Jackson were deeply engaged in humanitarian causes. Upon their first meeting, Jackson had already donated $188,000 to the youth-oriented Prince’s Trust charity and an additional $126,000 to the children’s charity at London’s Great Ormond Street Hospital. The two also shared a similar taste in jewelry, both being clients of Butler & Wilson, one of England’s leading fashion jewelers. But was their connection deeper than mere friendship and shared values?
Jackson’s former bodyguard, Matt Fiddes, confirmed the late-night calls, even claiming the singer was “in love” with Diana. Fiddes, who worked closely with Jackson for a decade, stated: “[Jackson] felt she was the only person in the world who could understand his life in terms of not being able to go anywhere, and the media stories that got out of hand… The intrusion into the private life, having no privacy whatsoever, the children being hounded.”
Michael Jackson and Princess Diana were also united by their shared experience with the paparazzi. For many years, both were likely among the most photographed individuals globally. Diana was constantly in the spotlight, her persona contrasting with the royal family, which always drew intense interest from tabloids and photographers alike. Similarly, Michael Jackson’s life story and ever-changing appearance made him a prime media target.
The pair are said to have remained friends until Diana’s tragic death in 1997. When Michael learned of her passing, he was devastated. According to The Express, the news reportedly hit the star so hard that he fainted and had to be revived with smelling salts. He also postponed a performance on his HIStory tour. The singer was scheduled to perform a concert in Belgium before an audience of 60,000, but organizers reported that Jackson was so stunned by Diana’s death that he was unable to take the stage. In a sad twist of fate, Diana died just two days after Michael’s 39th birthday. When he returned to the stage a couple of days later, he paid tribute to his late friend, expressing, “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, because you are the true princess of the people.’”
However, Michael did not attend Diana’s funeral. Instead, he went to a memorial service for her in Los Angeles, telling reporters that he wanted to be there to “honor my friend who is no longer here… I love her.” Dressed in black, sporting a black fedora and a red armband, Jackson arrived at the Los Angeles church surrounded by an entourage of bodyguards. He was one of 1,000 guests in attendance.
Michael Jackson spoke fondly of Diana on several occasions after her death. In 2003, he reiterated his feelings, calling her “one of the sweetest people I’ve ever known, because we could relate to each other.” He continued, “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.”
It is quite fascinating to observe Diana and Michael Jackson together. Sadly, both were gone before their time under tragic 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.
