You’ve recalled an iconic moment that belies just how deep their connection ran. That backstage encounter at Wembley Stadium on July 16, 1988—just before Michael’s Bad tour concert supporting the Prince’s Trust—was their only in-person meeting. But what seems like a fleeting crossover of fame was, they later revealed, the start of a genuine bond.
🎵 Their Wembley Encounter & the “Dirty Diana” story
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Princess Diana and Prince Charles attended Michael Jackson’s Wembley show in support of his charity work.
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Michael, aware of the sensitive subject matter, initially removed “Dirty Diana” from the setlist so as not to offend her royal presence.
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Yet Diana, revealing her playful side, cheekily insisted, “That’s my favourite song—make sure you do it.” Michael, flustered but charmed, managed to include it after all.
This exchange showcased their mutual respect and Diana’s fun-loving personality.
🎁 A Growing Friendship Filled with Empathy
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Michael gifted Diana two miniature tour jackets for her sons, William and Harry, accompanied by a charitable donation honoring her causes.
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Their bond, rooted in empathy for one another’s experiences, extended far beyond that evening. Michael shared that Diana would phone him late at night—sometimes after 3 a.m.—to share her struggles, including issues with the press and her children.
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While some close to Diana questioned whether she ever dialed him directly, their private conversations seemed to bring comfort to two public figures marred by relentless media scrutiny.
😢 Tragic Loss & Mutual Mourning
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Diana’s sudden death in August 1997 reportedly devastated Michael. He is said to have fainted upon hearing the news, requiring smelling salts, and even postponed a concert in Belgium due to shock.
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When he eventually returned to the stage, he paid tribute to her, calling her “the true princess of the people” and expressing love and admiration from the heart.
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Though Michael couldn’t attend her funeral in London, he honored her memory at a Los Angeles memorial service, dressed in black with a fedora, and speaking fondly of their unique bond.
💡 In Essence
That brief snapshot backstage holds so much more: a spirited crack at protocol when Diana demanded “Dirty Diana”; a blossoming intimacy where two global figures found solace and understanding in each other; and, ultimately, a shared grief that transcended fame.
What began as a curious meeting evolved into a quietly profound friendship—proof that even amidst unparalleled fame, genuine connections can take root.
