Princess Diana and Michael Jackson shared one of the most unexpected celebrity connections of the late 20th century, and their bond has continued to intrigue fans for decades.
Princess Diana and Michael Jackson’s meeting
The pair first met on July 16, 1988, when Diana attended Jackson’s Bad tour at Wembley Stadium alongside King Charles III, then-Prince of Wales.
At the time, Jackson had already shown his support for charitable causes close to the royal family, donating £150,000 to the Prince’s Trust and a further £100,000 to Great Ormond Street Hospital. Diana was reportedly a huge fan of his music, often listening to his albums Thriller and Bad.
Their backstage meeting quickly made headlines. Photos showed the two laughing and chatting warmly, suggesting an instant connection.
Why Michael Jackson did not wish to perform Dirty Diana for Princess Diana
However, one detail from the evening has become especially iconic. Jackson had removed the song Dirty Diana from his setlist, believing it would be inappropriate to perform it in front of the princess due to its subject matter.
Speaking later, he explained: “I took it out of the show in honor of Her Royal Highness.” But Diana surprised him. “Are you going to do Dirty Diana?” she asked. When he told her he had removed it, she insisted: “No! I want you to do it. Do it. Do the song.” During the concert, Diana was said to have danced enthusiastically, while Charles reportedly remained seated.
Following the show, Jackson gifted the royal couple tour jackets for their young sons, Prince William and Prince Harry, further cementing the friendly exchange.
Their friendship allegedly bloomed
In the years that followed, Jackson claimed their relationship continued from afar. He said: “We were very close… She was extremely close by phone… I was still married to Lisa Marie. 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 about children, the press.”
According to him, they bonded over the pressures of global fame and intense media scrutiny.
There has long been speculation that Jackson’s feelings for Diana went beyond friendship. In a taped conversation with a confidante, he admitted: “I loved her very much. She was my type, for sure.”
His former bodyguard later claimed that Jackson saw Diana as his “ideal wife” and even dreamed of marrying her.
Michael Jackson was “in love” with Princess Diana
When Diana died in 1997, Jackson was said to be devastated. He cancelled several dates of his HIStory tour and later recalled collapsing in grief when he heard the news.
When he eventually returned to the stage, he paid tribute to her, saying in an interview that during his return to stage he was saying: “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever. Because you are the true princess of the people.’”
Although Jackson did not attend her funeral, he honoured her at a memorial in Los Angeles, explaining he did so out of his “love” for her. Years later, he continued to describe Diana as one of the “sweetest people” he had ever known.
Whether their bond was a deep friendship or something more, the connection between Diana and Jackson remains one of the most fascinating crossovers between royalty and pop culture.
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