At first, it appears to capture nothing more than a brief meeting between two global icons. But look closer, and their story reveals a deeper and more intriguing connection.
Neither Princess Diana nor Michael Jackson needs much introduction. Their fame alone made it unsurprising that their paths would cross. What few expected, however, was that their encounter would spark a bond that went far beyond polite conversation.
Their Only Face-to-Face Meeting
Diana, often called “the People’s Princess,” was a devoted music fan. While she famously loved Duran Duran, her record collection also included Michael Jackson albums. She reportedly played Thriller and Bad repeatedly, showing genuine admiration for his work.
Their shared love of music led to their only in-person meeting on July 16, 1988, when Diana and her then-husband, Prince Charles, attended Jackson’s Bad tour concert at Wembley Stadium. This would be both their first and last face-to-face encounter.
“She told me she was honored to meet me,” Jackson recalled in a 1997 interview with Barbara Walters.
Despite the warm words, Jackson admitted he felt extremely nervous meeting Diana, something evident in photographs from the evening. Part of the awkwardness stemmed from his decision to remove “Dirty Diana” from the setlist, fearing the song’s subject matter might offend her.
“I took it out of the show in honor of Her Royal Highness,” he told Walters.
Diana’s Unexpected Response
Diana, however, was unimpressed by the omission. During their pre-show meeting, she asked Jackson whether he planned to perform “Dirty Diana.” When he explained why he had removed it, she insisted he sing it anyway. In the end, he did.
Jackson later spoke warmly of her, saying, “I thought the princess was just wonderful.”
Aware of how devoted Diana was to her children, he also gifted her two miniature tour jackets for Princes William and Harry. Throughout the concert, Diana reportedly danced enthusiastically, while Prince Charles remained seated.
Rumours of a Deeper Bond
What surprised many was how their brief meeting reportedly led to a close personal connection. Jackson later claimed they stayed in frequent contact.
“We were very close,” he told German media in 1999. “She was extremely close by phone… Diana woke me up usually late at night… mostly after three in the morning!”