Princess Diana & Michael Jackson's Friendship: Although Worlds Apart, They Were Linked By Shared Passions & Tragedy

Apr 17, 2025 by apost team

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When two of the most iconic figures of the 20th century crossed paths in 1988, their unlikely friendship captured the imagination of the whole world. Princess Diana, whose compassion led to her being known as “the People’s Princess,” and Michael Jackson, the enigmatic “King of Pop,” shared an intriguing and deeply human bond. Though their lives and experiences were worlds apart, their connection revealed a mutual understanding born out of shared experiences of fame, philanthropy, and an enduring desire to make a difference. While these two figures had little in common at first glance, understanding their personalities, fears and hopes makes it inevitable that they would be friends. 

While the Princess spent her life in the royal family, meeting countless influential people and making conversation, her interaction with Jackson left an impact on both of them. Though they met only once, it was enough for them to relate to one another and forge a bond of friendship that remains an object of fascination long after they both passed. 

Princess Diana was already a fan of the singer prior to their meeting in 1988, having been impressed by his albums “Thriller” and “Bad.” She and then Prince Charles attended the Wembley leg of his “Bad” tour and met the King of Pop, who had made sizable donations to charity. The events of this concert are both fascinating and amusing.

Princess Diana and Jackson were both humbled to meet one another despite her being a royal and he a global superstar. He shared this in an interview the year she died, saying:

“She told me she was honoured to meet me.”

Speaking to Barbara Walters in 1997, Jackson shared that he was nervous about performing his hit song “Dirty Diana” in front of the Princess and wanted to remove it from the setlist. The song, written about a rock groupie, would’ve been too inappropriate to sing in front of a princess who shared the same name. 

“I took it out of the show in honor of Her Royal Highness,” Jackson told Walters. “Are you going to do ‘Dirty Diana’?” the Princess asked him during the meet-and-greet before the show. “I said, ‘No, I took it out of the show because of you.’ She said, ‘No! I want you to do it. Do it. Do the song.’” 

Diana reportedly danced throughout the concert while Prince Charles remained seated. Jackson went on to gift the Prince and Princess of Wales two miniature tour jackets for their sons, Prince William and Prince Harry. 

Jackson and Princess Diana were both hounded by paparazzi and the media, the latter to her death. When she died, he paid his respects, joining many heartbroken fans in mourning the late Princess in a Los Angeles church. The late King of Pop said he was there “in honor of my friend, who is no longer here. I love her.”

Now that they are no longer here, we can’t help but miss the People’s Princess and the King of Pop and cherish their friendship and memories.

apost.com

What do you think about this friendship? Do you agree that they had more in common than we thought? Let us know your thoughts, and then pass this on to friends and family who miss them, too!