The “King of Pop” and the “People’s Princess” — two of the most recognized names in modern history — shared not only iconic titles but also a deep, personal connection. Michael Jackson and Princess Diana formed a unique friendship, rooted in their mutual love of music, humanitarian efforts, and the burden of living under relentless media scrutiny.

Their connection began publicly on July 16, 1988, when Diana and her then-husband, Prince Charles, attended Jackson’s Bad tour concert at Wembley Stadium. Jackson, ever the humanitarian, had donated £150,000 to the Prince’s Trust charity at the time. Though thrilled to perform for royalty, Jackson reportedly removed the track “Dirty Diana” from his setlist, fearing it might offend the Princess. However, Diana intervened, insisting he keep the song in the show — as it was one of her personal favorites.

That first meeting was just the beginning. Despite only meeting face-to-face once, the bond between the pop star and the Princess grew stronger through countless late-night phone calls. Jackson, in multiple interviews, revealed that Diana often called him after 3 a.m., sharing her worries about the press, her children, and her life under a microscope. He recalled these conversations with great fondness, describing them as comforting and deeply emotional.

“She was extremely close by phone,” Jackson once said. “She woke me up usually late at night… and then she held me for hours on the telephone.” According to his former bodyguard Matt Fiddes, Jackson even confided that he was “in love” with Diana, feeling she was the only person who truly understood the unique pressures of fame. Both were subject to intense media scrutiny, with Diana being the most photographed woman in the world and Jackson enduring endless tabloid speculation.

They shared a deep distrust of the press and paparazzi, both having experienced the violation of their privacy for most of their adult lives. This mutual understanding created a powerful emotional connection that few others could ever comprehend.

The friendship endured until Diana’s tragic death in a car crash on August 31, 1997. Jackson, devastated by the news, collapsed in tears and postponed his scheduled performance on the HIStory tour. When he returned to the stage, he honored Diana by dedicating the song “Gone Too Soon” to her — a ballad he had originally written for his young friend Ryan White, a victim of AIDS. The choice of song was especially poignant, as both Diana and Jackson had worked to de-stigmatize HIV/AIDS in their lifetimes.

Although Jackson did not attend Diana’s funeral in London, he was present at a memorial held in Los Angeles. There, he told reporters, “I’m here in honor of my friend who is no longer here… I love her.”

In a 2003 interview, Jackson reflected, “She was one of the sweetest people I’ve ever known. We shared something in common — with the press. I don’t think they hounded anyone more than her and myself. We had a relationship where we would call each other late at night and just cry on each other’s shoulders.”

Ironically, both Diana and Jackson were later interviewed by journalist Martin Bashir, whose controversial style was criticized in both cases. Jackson reportedly agreed to Bashir’s interview based on Diana’s earlier participation — a decision both would ultimately come to regret.

Following Jackson’s own death in 2009 at the age of 50, the full extent of his relationship with Diana remains something of a mystery. The contents of those 3AM conversations are known only through Jackson’s recollections, and yet they hint at a deeply human connection between two global icons who, despite their immense fame, often felt isolated in their private lives.

Interestingly, Jackson’s televised memorial became the second most-watched daytime funeral in U.S. history — drawing 31 million viewers. The most-watched? Diana’s own funeral, which drew over 33 million American viewers in 1997.

Their lives were worlds apart, yet bound by shared pain, compassion, and a yearning for normalcy. Whether their connection was purely platonic or something deeper is left to speculation. But one thing is certain: the friendship between Michael Jackson and Princess Diana was as real as it was rare — a bond forged in the shadows of fame, and forever etched in pop culture history.