A striking photograph of Princess Diana standing beside Michael Jackson captures what appears, at first glance, to be a brief encounter between two global icons. Yet behind that single image lies a far more intriguing story—one that hints at an unexpected bond between the Princess of Wales and the King of Pop.
Few figures in modern history are as instantly recognizable as Diana and Jackson. Their fame alone made a meeting seem inevitable. What no one could have predicted, however, was that their brief encounter would spark a connection that resonated deeply with both of them.
A meeting that happened only once
Princess Diana was a passionate music lover. In the 1980s, she openly adored Duran Duran, but her record collection also included Michael Jackson’s albums. In fact, she reportedly played Thriller and Bad repeatedly, making Jackson’s music a regular presence in her private life.
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| Diana, Princess of Wales (1961 – 1997) meets singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. (Photo by Princess Diana Archive/Getty Images) |
That admiration led to their only face-to-face meeting on July 16, 1988. Diana attended Jackson’s Bad tour concert at Wembley Stadium alongside her then-husband, Prince Charles. Though it would be their first and last in-person meeting, it left a lasting impression on both of them.
“She told me she was honored to meet me,” Jackson later recalled in a 1997 interview with Barbara Walters.
Despite his superstar status, Jackson admitted he was deeply nervous about meeting the princess. The tension was evident in photographs from that night, lending an awkward edge to their initial interaction.
The reason for his anxiety was unexpected. Jackson had removed one song—“Dirty Diana”—from the setlist, worried that its subject matter might offend her. The song, which tells the story of a rock groupie, felt inappropriate to perform in front of a royal.
“I took it out of the show in honor of Her Royal Highness,” Jackson explained.
Diana’s unexpected response
To Jackson’s surprise, Diana wasn’t pleased by the omission. During a pre-show meet-and-greet, she asked whether he planned to perform “Dirty Diana.” When he explained why he had removed it, she encouraged him to sing it anyway.
Ultimately, Jackson gave in—and performed the song.
Jackson later spoke warmly of Diana, praising her kindness and grace. Aware of how devoted she was to her sons, Princes William and Harry, he gifted her two miniature tour jackets for them.
While Diana danced throughout the concert, clearly enjoying herself, Prince Charles reportedly remained seated.
Was there something more?
That single meeting marked the beginning of what Jackson later described as a meaningful relationship.
“We shared a deep connection,” he told German media in 1999. “She was always just a phone call away.”
At the time, Jackson was married to Lisa Marie Presley. He claimed Diana often called him late at night—sometimes after 3 a.m.—and that their conversations would last for hours, usually centering on her children and her struggles with the media.
According to Jackson, these calls didn’t go unnoticed. “Lisa Marie would get jealous,” he said, claiming she would sometimes pick up another phone to listen in.
The truth behind these late-night conversations remains unclear. Friends of Diana later told The Express that Jackson did not have her private number and that palace staff were instructed not to put his calls through. Still, what’s undeniable is that the two shared remarkably similar lives.
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| Prince Charles and Diana, Princess of Wales (1961 – 1997) meet singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. Jackson is presenting the Prince with a cheque for the charity. (Photo by Princess Diana Archive/Getty Images) |
Both were relentless targets of paparazzi intrusion and tabloid scrutiny. Both were deeply committed to charitable causes. On the night they met, Jackson donated $188,000 to The Prince’s Trust and an additional $126,000 to Great Ormond Street Hospital’s children’s charity.
They even shared an appreciation for fine jewelry, both being patrons of the renowned British jeweler Butler & Wilson.
Jackson’s former bodyguard, Matt Fiddes, later claimed the singer’s feelings ran deeper than friendship.
“Michael felt she was the only person in the world who could truly understand his life,” Fiddes said. “The lack of privacy, the media pressure, the children being chased—it bonded them.”
Jackson’s reaction to Diana’s death
Princess Diana’s death in 1997 reportedly devastated Jackson. According to The Express, he was so overcome by the news that he fainted and had to be revived with smelling salts.
He postponed a scheduled performance on his HIStory tour in Belgium, with organizers explaining that he was too shaken to appear on stage. Tragically, Diana died just two days after Jackson’s 39th birthday.
When he eventually returned to performing, Jackson paid tribute to her from the stage.
“In my heart, I was saying, ‘I love you, Diana. Shine on forever, for you are the true princess of the people,’” he said.
Did he attend her funeral?
Jackson did not attend Diana’s funeral in London. Instead, he took part in a memorial service in Los Angeles, where he arrived dressed in black, wearing a fedora and a red armband, accompanied by bodyguards.
“I wanted to honor my friend,” he told reporters. “I love her.”
In the years that followed, Jackson continued to speak affectionately of Diana. In 2003, he described her as “one of the sweetest people I’ve ever known.”
“We shared something with the press,” he said. “They didn’t hound anyone more than her and myself. We would call each other late at night and cry on each other’s shoulders about how cruel the tabloids could be.”
Their lives unfolded along strikingly similar paths—defined by adoration, intrusion, and tragedy—and while they met only once, the bond they shared left a lasting mark on them both.
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