Behind the scenes of Diana and Michael Jackson’s connection

There is a singular, striking image from 1988 that has become a permanent fixture in the archives of pop culture: Princess Diana and Michael Jackson standing side-by-side. At a cursory glance, it appears to be nothing more than a high-wattage meeting between two of the 20th century’s most recognizable legends. However, if one peels back the layers of that encounter, a much more complex and deeply human narrative begins to emerge. Neither Diana nor Jackson requires a formal introduction; their status as global deities is absolute. While it was perhaps inevitable that their paths would cross, few could have predicted that a single meeting would catalyze a bond that—according to Jackson—transcended the typical “polite small talk” of celebrity circles.

A Single Meeting at Wembley

Ironically, the two icons met in person only once. The date was July 16, 1988, at London’s Wembley Stadium during Jackson’s seminal Bad tour. Diana, a self-confessed music aficionado who famously championed Duran Duran, was also a devoted fan of Jackson’s work, reportedly playing Thriller and Bad on a continuous loop in her private quarters.

Jackson would later tell interviewer Barbara Walters in 1997 that he felt “incredibly nervous” before shaking hands with the Princess. That tension is palpable in the photography from the day. The initial awkwardness was fueled by a last-minute creative decision: Jackson had scrubbed the hit “Dirty Diana” from the evening’s setlist, fearing the title and subject matter—a song about a rock groupie—would be perceived as a slight against the royal guest.

However, the “People’s Princess” had other ideas. During the pre-show meet-and-greet, she pointedly asked Jackson if the song was on the program. When he admitted he had removed it out of respect for her, she insisted he put it back in, reportedly encouraging him to perform the track. Jackson complied, bolstered by her enthusiasm.

Late-Night Confessions and “Telephonic Solace”

While their physical meeting was a one-time event, Jackson claimed it ignited a powerful, long-distance connection. By 1999, Jackson was telling German media outlets that the two had become “very close” via the telephone.

“She woke me up usually late at night… mostly after three in the morning!” Jackson claimed, describing marathons of conversation that lasted for hours. According to the singer, Diana would “hold him” on the line, venting her frustrations regarding the relentless press and her concerns for her sons, William and Harry. Jackson even quipped that his then-wife, Lisa Marie Presley, would listen in from another room out of jealousy.

The veracity of these late-night calls remains a point of contention among royal biographers. Friends of the Princess told The Express that Jackson likely never had her private line and that Kensington Palace staff were famously protective. Yet, Jackson’s former bodyguard, Matt Fiddes, corroborated the claims, going as far as to suggest Jackson was “in love” with Diana. Fiddes argued that Jackson viewed Diana as the only person on Earth who could truly empathize with his level of isolation—the inability to walk down a street and the constant, predatory nature of the paparazzi.

A Shared Mission and a Mirror Image

Beyond the rumors of late-night phone calls, the two were undeniably united by their humanitarian efforts. On the day of their meeting, Jackson donated a combined $314,000 to the Prince’s Trust and Great Ormond Street Children’s Hospital. They even shared a specific aesthetic taste, both being frequent patrons of the British fashion jeweler Butler & Wilson.

But the strongest tether between them was their shared status as the most hunted individuals on the planet. Both were prime targets for the tabloids—Diana for her subversion of royal norms, and Jackson for his increasingly eccentric public persona.

The Aftermath of a Tragedy

The depth of their friendship was perhaps most evident in Jackson’s reaction to Diana’s death in 1997. Upon hearing the news in a Belgium hotel, Jackson reportedly fainted and required revival with smelling salts. He postponed his HIStory tour performance for 60,000 fans, stating he was too “stunned” to take the stage.

When he did return to the spotlight, he dedicated his performance to her: “In my heart, I was saying, ‘I love you, Diana. Shine. And shine on forever, because you are the true princess of the people.’”

Though Jackson did not attend the state funeral in London, he made a somber, high-profile appearance at a memorial service in Los Angeles. Clad in his signature black fedora and a red armband, he told reporters he was there to “honor my friend.”

In hindsight, that 1988 photograph captures more than a celebrity handshake; it captures the first tentative steps of a relationship built on mutual recognition. Both lived under the white-hot heat of a spotlight that eventually consumed them both, leaving behind a legacy of two individuals who, in their own words, simply “cried on each other’s shoulders.”