An unforgettable image of Princess Diana and Michael Jackson has always stayed with me.
At first, it might look like a simple moment between two icons, but their story goes much deeper than that.
Did you know their connection held more than what meets the eye?
Both Princess Diana and Michael Jackson are legends in their own right, their names alone conjuring memories and admiration. While it’s not surprising that these two extraordinary figures would eventually cross paths, few would have expected that their meeting would lead to something beyond a brief exchange of pleasantries.
Their only in-person meeting happened on July 16, 1988, backstage at Wembley Stadium in London before Michael’s Bad tour concert. Diana, known affectionately as “The People’s Princess,” was a music lover with a special fondness for Duran Duran, but she also enjoyed Michael Jackson’s music. His albums Thriller and Bad were reportedly on repeat in her collection.
When Diana and Prince Charles attended Michael’s concert that evening, it marked both the beginning and end of their in-person connection. “She told me she was honored to meet me,” Michael shared in a 1997 interview with Barbara Walters.
Michael later recalled feeling incredibly nervous when shaking Diana’s hand—a tension evident in photos from that day. Part of this unease stemmed from a decision he’d made out of respect: he had removed the song “Dirty Diana” from the setlist, fearing it might offend her. The song, which is about a rock groupie, felt inappropriate to perform with the princess in the audience.
“I took it out of the show in honor of Her Royal Highness,” Michael explained to Walters, reflecting on his gesture toward Diana’s presence.
Diana’s Reaction to Meeting Michael Jackson
However, Michael’s choice to remove “Dirty Diana” from the concert didn’t go as he expected.
During their meet-and-greet, Diana asked if he planned to perform the song. When he explained he’d cut it from the setlist out of respect, she surprised him by urging him to keep it in, encouraging him to sing it. In the end, Michael performed “Dirty Diana” as part of the show.
Michael clearly admired Diana and held deep respect for her. “I thought the princess was just wonderful,” he shared with reporters.
Understanding her devotion to her sons, Michael gifted her two miniature tour jackets for Princes William and Harry.
An enthusiastic pop music fan, Diana was said to have danced throughout the concert, while Prince Charles remained seated, watching from the sidelines.
Was Michael Jackson in Love with Diana?
What many may not have expected was that their first meeting in 1988 would spark a remarkably strong bond between them.
“We were very close,” Jackson revealed to 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.”
Michael mentioned that their late-night conversations often lasted for hours, indicating a deep connection.
”Lisa Marie used to get so jealous she would go into the other room, pick the receiver and listen in,” he recalled, highlighting the intensity of his relationship with Diana.
Whether the late-night calls actually took place is still unverified. According to Diana’s friends who spoke to “The Express”, Jackson reportedly never had her private number. If he called Kensington Palace, the staff were instructed not to connect him to the princess.
However, what is clear is that both shared similar experiences and a deep passion for the same causes.
Both Diana and Michael were passionately involved in charitable causes. At the time of their meeting, the humanitarian Jackson had contributed $188,000 to the youth-focused Prince’s Trust charity and an additional $126,000 to the children’s charity at London’s Great Ormond Street Hospital.
They also shared a fondness for jewelry, both being clients of Butler & Wilson, one of England’s top fashion jewelers.
But was there something more than just friendship and shared interests?
Jackson’s former bodyguard, Matt Fiddes, confirmed the existence of those late-night calls, even asserting that the singer was “in love” with Diana. Fiddes, who worked closely with Jackson for a decade, shared:
How Did Michael Jackson React to Diana’s Death?
One of the connections between Michael Jackson and Princess Diana was their shared experience with the relentless paparazzi. Both were among the most photographed individuals for many years. Diana, with her captivating persona that contrasted sharply with the royal family, was perpetually in the spotlight, attracting the attention of tabloids and photographers. Similarly, Michael’s life story and evolving appearance made him a prime target for media scrutiny.
The two are said to have maintained their friendship until Diana’s tragic death in 1997.
When Michael learned of her passing, he was heartbroken. According to “The Express”, the news hit him so profoundly that he fainted and had to be revived with smelling salts upon hearing about it.
He also postponed a performance on his HIStory tour. Scheduled to perform in Belgium before an audience of 60,000, the concert organizers reported that Michael was too overwhelmed by the news to take the stage.
In a poignant twist of fate, Diana died just two days after Michael’s 39th birthday.
Upon returning to the stage a few 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.’”
“[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.”
Did Michael Jackson Attend Diana’s Funeral?
Michael did not attend Princess Diana’s funeral. Instead, he chose to participate in a memorial service for her in Los Angeles, where he expressed his desire to be there to “honor my friend who is no longer here… I love her.”
Dressed in black, 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 one of approximately 1,000 guests in attendance.
Michael Jackson spoke fondly of Princess Diana on multiple occasions following her death. In 2003, he reflected on their connection, describing her as “one of the sweetest people I’ve ever known, because we could relate to each other.”
He added, “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.”
