The “Dirty Diana” Dilemma
An interesting detail about that meeting lies in Jackson’s concert setlist. Originally, he had planned to perform the song “Dirty Diana,” a track from the Bad album about a groupie.
Concerned that the song might be inappropriate with a female royal in attendance, Jackson removed it from the performance. In his own words, “I took it out of the show in honor of Her Royal Highness.”
Ultimately, Jackson performed “Dirty Diana,” and the moment became one of the many ways their personalities complemented each other — he was conscientious, she was persuasive and confident in her opinions.
A Connection Beyond the Concert
While the Wembley meeting was brief, it marked the beginning of a unique friendship that would extend beyond casual greetings and public appearances. Michael Jackson expressed admiration for Diana, describing her as “just wonderful” in interviews and praising her warmth and sincerity.
He also acknowledged her dedication to her children, gifting miniature tour jackets from his Bad tour to Princes William and Harry — a thoughtful gesture reflecting his understanding of family bonds.
Diana’s enthusiasm for pop music was evident during the concert; sources suggest she danced throughout the show, while Prince Charles remained seated, observing quietly. This contrast highlighted Diana’s free-spirited nature and her ability to enjoy moments of normalcy amid a life dominated by royal protocol.
Late-Night Conversations and Emotional Support
What few anticipated was that their friendship would evolve into a meaningful emotional connection. In interviews with German media in 1999, Jackson revealed that he and Diana remained in touch long after their initial meeting. He claimed, “We were very close.
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 mostly about her children, and the press.”
While some sources question the veracity of these late-night conversations — particularly as Diana reportedly did not share her private phone number with Jackson — what remains clear is that the two shared a deep understanding of fame, intrusion, and personal struggle.
Shared Humanitarian Interests
Beyond their personal connection, both Diana and Jackson were committed to humanitarian work. Michael Jackson had made donations to youth and children’s charities in the United Kingdom, including the Prince’s Trust and Great Ormond Street Hospital, before and after meeting Diana. Likewise, Diana was renowned for her charitable efforts, advocating for children’s hospitals, HIV/AIDS awareness, and numerous other causes.
The pair even shared tastes in fashion and jewelry, reportedly both being clients of Butler & Wilson, a prestigious British jewelry brand. These shared interests further solidified their bond, bridging worlds of celebrity, philanthropy, and personal taste.
Mutual Experiences With Media Scrutiny
Perhaps one of the most poignant elements of their relationship was their shared experience with relentless media attention. Both Jackson and Diana were subjected to intense paparazzi coverage, often facing speculation, rumors, and intrusion into their personal lives.
This common struggle created an unspoken understanding, and they reportedly used their conversations to support one another emotionally, discussing the pressures and invasions of privacy they each endured.
The tragic death of Princess Diana in 1997 left the world in shock, but for Michael Jackson, it was deeply personal. The two had shared a bond shaped by mutual admiration, empathy, and the unique pressures of fame, and Jackson’s reaction to her passing reflected the depth of their connection.
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