Princess Diana and Michael Jackson are two of the most legendary figures of the 20th century, both captivating the world in their own unique ways. While they came from entirely different backgrounds, their brief but meaningful interaction in 1988 has continued to spark public interest. Their meeting, though fleeting, revealed a surprising bond that many never expected.
A Meeting of Icons: Wembley Stadium, 1988
On July 16, 1988, Princess Diana and her then-husband, Prince Charles, attended a concert at London’s Wembley Stadium during Michael Jackson’s Bad tour. This event marked the one and only time that the “People’s Princess” and the “King of Pop” met in person.
Jackson, who was known for his electrifying performances, was understandably nervous before shaking hands with Diana. He later admitted in a 1997 interview with Barbara Walters that he was in awe of her presence. “She told me she was honored to meet me,” he recalled.
Adding to the tension, Jackson had made a last-minute change to his concert setlist out of respect for Diana. He decided to remove his hit song Dirty Diana, fearing that it might be inappropriate given her attendance. However, this move ended up surprising Diana herself.
Princess Diana’s Reaction to Michael Jackson’s Decision
Before the concert began, during a brief backstage meeting, Princess Diana directly asked Michael if he would be performing Dirty Diana. When he explained that he had removed it from the setlist out of respect, she reportedly urged him to keep it in the show, saying she wanted to hear it. Jackson, surprised and delighted, agreed to go ahead with the performance.
Diana’s enthusiasm for music was well known. She was a big fan of pop artists, with Duran Duran being one of her favorite bands. However, she also had a deep appreciation for Michael Jackson’s music, often playing his albums Thriller and Bad at home.
Jackson’s admiration for Diana was equally evident. He later shared how much he respected her humanitarian work and kindhearted nature. As a gesture of goodwill, he gifted her two miniature versions of his tour jackets for her sons, Prince William and Prince Harry.
A Friendship Beyond the Concert
Following their encounter, Michael Jackson and Princess Diana reportedly remained in contact. According to Jackson, they spoke on the phone multiple times, often discussing their struggles with the media and public life. He claimed that Diana would call him late at night, seeking comfort in conversations about her children and the relentless scrutiny they both faced.
In an interview with German media in 1999, Jackson described their connection: “We were very close. She was extremely close by phone… She talked mostly about her children and the press.”
However, some sources from Diana’s inner circle have disputed this, claiming that she never had private phone conversations with Jackson. According to a report from The Express, Diana’s staff had instructions not to put Jackson’s calls through to her. Whether or not these conversations actually took place remains uncertain, but the connection Jackson felt with Diana was undeniable.
A Shared Understanding: Life in the Public Eye
Despite their different worlds—one royal, the other an international pop icon—Diana and Michael Jackson had something in common: an overwhelming level of media attention. Both faced intense public scrutiny, with every aspect of their lives making headlines.
Diana’s position within the royal family and her public divorce from Prince Charles made her one of the most photographed women in the world. Similarly, Jackson’s changing appearance and personal life became a subject of endless speculation. They both understood the pressures of fame in ways that few others could.
Jackson’s former bodyguard, Matt Fiddes, later claimed that Jackson deeply admired Diana and even harbored romantic feelings for her. “He felt she was the only person in the world who could understand his life,” Fiddes said. However, this claim remains speculative, as there is no confirmed evidence that their relationship was anything beyond friendship and mutual admiration.
Michael Jackson’s Reaction to Diana’s Passing
Tragically, Princess Diana’s life was cut short in a car accident in Paris on August 31, 1997. News of her passing sent shockwaves around the world, and Jackson was reportedly devastated upon hearing it.
Some reports suggested that he was so overwhelmed by grief that he fainted and had to be revived with smelling salts. While this claim has not been widely verified, it is known that he postponed a scheduled concert on his HIStory tour in Belgium out of respect for Diana’s passing.
During a tribute performance shortly after, Jackson shared his thoughts with the audience: “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 he did not attend Diana’s funeral in London, he later attended a memorial service for her in Los Angeles, where he expressed his sorrow and admiration for her. Speaking to reporters, he said, “I wanted to be here to honor my friend who is no longer here… I love her.”
Their Enduring Legacies
Despite their lives being tragically cut short, Princess Diana and Michael Jackson continue to be celebrated for their contributions to the world. Diana’s legacy as a humanitarian and advocate for various charitable causes remains a powerful symbol of compassion and kindness. Jackson’s influence on music, dance, and entertainment remains unmatched, with his work continuing to inspire new generations.
Their one and only meeting in 1988 may have been brief, but it symbolized a connection between two of the most famous people of their time. The moment captured in photographs that night at Wembley Stadium serves as a reminder of their influence, their struggles, and the impact they left on the world.
Conclusion
The iconic image of Princess Diana and Michael Jackson meeting backstage at Wembley Stadium is more than just a snapshot in time—it represents a rare intersection of two legendary figures who understood each other in ways few could.
While rumors and speculation about their relationship have surfaced over the years, what remains undeniable is the mutual respect and admiration they had for each other. Their lives, marked by both extraordinary success and immense personal challenges, continue to fascinate the world decades after their passing.
Even though they only met once, the connection between Diana and Jackson remains one of the most intriguing stories in pop culture history. Their legacies live on, ensuring that their influence and contributions will never be forgotten.
