Behind the scenes of Diana and Michael Jackson’s connection

A memorable photograph of Princess Diana and Michael Jackson has always remained vivid in my mind.

On July 16, 1988, Diana, Princess of Wales (1961 – 1997), met the renowned singer Michael Jackson backstage at Wembley Stadium in London, prior to his concert benefiting the Prince’s Trust charity. (Photo by Princess Diana Archive/Getty Images)

Their only in-person encounter
Diana, affectionately referred to as “The People’s Princess,” was an avid music enthusiast. Notably, her favorite band was Duran Duran, whose music she particularly enjoyed during the 1980s.

In addition to Duran Duran, Diana’s music collection included albums by Michael Jackson, indicating her appreciation for his work as well. It is reported that she frequently played his albums, Thriller and Bad.

The occasion that brought Diana and Michael together on July 16, 1988, was his concert during the Bad tour.

On that day, she and her then-husband, Prince Charles, attended the concert at Wembley Stadium, which turned out to be both their first and last meeting.

“She told me she was honored to meet me,” Jackson recounted in a 1997 interview with Barbara Walters.

Michael expressed that he felt extremely anxious before greeting Diana, a sense of tension that is palpable in the photographs from that day. The initial awkwardness of their meeting can be attributed to a specific decision made by the superstar.

He had chosen to exclude the song “Dirty Diana” from his concert setlist, fearing it might offend her. Given that the song addresses the theme of a rock groupie, he believed it would be inappropriate to perform in the presence of a royal.

“I took it out of the show in honor of Her Royal Highness,” Jackson explained to Barbara Walters in 1997. Diana’s response to meeting Michael Jackson, however, was quite different.

During their meet-and-greet before the performance, Diana inquired whether he would be singing “Dirty Diana.” Upon learning that he had removed it from the setlist due to her attendance, she encouraged him to perform it, urging him to go ahead and sing the song.Recognizing 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 chose to remain seated.

Was Michael Jackson romantically interested in Diana? Many may not have expected that their initial meeting in 1988 would spark a remarkably strong connection.

“We were very close,” Jackson recounted to German media in 1999. “She was very accessible by phone… At that time, I was still married to Lisa Marie [Presley]. Diana would often call me late at night… usually after three in the morning! We would talk for hours, and she primarily discussed 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 go into another room to pick up the receiver and listen in,” he remarked.

The authenticity of these late-night conversations remains uncertain. According to friends of Diana who spoke to The Express, Jackson allegedly did not possess her private number. If he attempted to call Kensington Palace, the staff were instructed not to connect him to the princess.

However, it is evident that both shared similar experiences and a commitment to the same causes. Diana and Michael were both actively involved in humanitarian efforts. At the time of their meeting, the philanthropic 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 had a mutual appreciation for jewelry, as both were clients of one of England’s prominent fashion jewelers, Butler & Wilson.

But was there a deeper connection beyond friendship and shared ideals?

Jackson’s former bodyguard, Matt Fiddes, corroborated the existence of the late-night calls, even suggesting that the singer was “in love” with Diana.

Fiddes, who worked closely with Jackson for ten years, stated: “[Jackson] believed she was the only person in theHow did Michael Jackson respond to the passing of Diana?

Both Michael Jackson and Princess Diana shared the common experience of dealing with paparazzi, as they were two of the most photographed figures for an extended period.

Diana was perpetually in the public eye, and her distinct persona, which often clashed with that of the royal family, attracted significant attention from tabloids and photographers. In a similar vein, Michael Jackson’s life narrative and his evolving appearance rendered him a frequent subject of media scrutiny.