Inside Michael Jackson’s Close Friendship With Princess Diana

The People’s Princess and the King of Pop shared more than just honorific royal titles. Diana, Princess of Wales and mother to the future King of England developed a strong friendship with global music sensation Michael Jackson due to her love of his songs, their mutual passions for creating good in the world and the common experience of having their individual lives play out under constant media scrutiny.

Much to her dismay, Jackson didn't want to perform "Dirty Diana" in front of the Princess

Already a huge fan (she reportedly listened to the albums Thriller and Bad repeatedly), Diana and Jackson met July 16, 1988, when, along with her then-husband Prince Charles, she attended Wembley Stadium for Jackson’s Bad tour. At the time, humanitarian Jackson had donated £150,000 for the youth-oriented Prince’s Trust charity and a further £100,000 for the children’s charity of London’s Great Ormand Street Hospital.

Jackson, who spoke of his relationship with Diana numerous times during his life, was nervous of meeting the Princess for the first time ahead of his performance and had decided to remove the song “Dirty Diana” from the concert’s setlist. He was worried the track, about a rock groupie, would be inappropriate to perform before a member of royalty-bearing the same name. On hearing of his decision, Diana asked him not to exclude the song as it was one of her favorites by the artist.

“I took it out of the show in honor of Her Royal Highness,” Jackson told Barbara Walters in 1997 of their first meeting. “Are you going to do Dirty Diana?” Jackson recalled Diana asking him during the meet-and-greet before the show. “I said, ‘No, I took it out of the show because of you.’ She said, ‘No! I want you to do it. Do it. Do the song.’” Diana reportedly danced during the concert as Prince Charles remained seated. Jackson also gifted the couple two miniature tour jackets for their sons, Princes William and Harry.

Jackson said the pair were 'very close'

Diana and Jackson had an easy rapport and their friendship developed over time and across geographic boundaries. “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 about children, the press.”

Jackson’s former bodyguard Matt Fiddes corroborates the late-night calls, going as far as to say the singer was “in love” with Diana. Fiddes, who worked closely with Jackson for a decade, told Daily Star Online in 2017, “[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.”

The pair shared a mutual distrust of the growing media presence in their lives, especially the paparazzi who relentlessly chronicled their every public moment. Before, during and after her marriage to Prince Charles, Diana was the most photographed person in the world. Jackson’s ever-changing appearance and erratic behavior (such as dangling his baby over a balcony in front of fans) had tabloids speculating over his every appearance.

Though they would only meet in person once during their lifetimes, their friendship endured until Diana’s death on August 31, 1997, according to Jackson. On hearing the news of her passing, Jackson told Walters he fell down in grief and cried. In shock, Jackson postponed a scheduled performance of his HIStory tour. When he did return to the stage, he dedicated the performance to Diana. “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 was not present at Diana’s London funeral alongside other friends of the late Princess, including Elton John and George Michael, but attended a memorial service for her held in Los Angeles where he told reporters he was there in “honor of my friend who is no longer here… I love her.”

After her death, Jackson continued to put Diana on a pedestal

Recalling their friendship in 2003, Jackson reportedly said of Diana that she “was one of the sweetest people I’ve ever known, because we could relate to each other. 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.”

Following Jackson’s death in 2009 aged 50, the true depth of his friendship with Diana and the exact content of those late-night conversations remains unknown other than Jackson’s retelling.

More than 31 million American viewers tuned in to watch the coverage of Jackson’s memorial service on July 7, 2009, according to Nielsen ratings, making it the second-most watched daytime funeral the ratings service had measured. The first, on September 6, 1997, was that of his friend Diana, Princess of Wales, whose funeral drew 33.2 million viewers.

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