One of the most striking images from the 1980s captures Princess Diana and Michael Jackson together—a single moment that hints at a deeper connection. Although they only met in person once, the bond between them was far more than just a polite encounter.

Both icons in their own right, Diana and Michael’s paths crossed on July 16, 1988, backstage at Michael Jackson’s Bad tour concert at Wembley Stadium in London. It was a charity event benefiting the Prince’s Trust, an organization dedicated to youth development, and marked the beginning and end of their in-person meetings.

A Friendship Sparked by a Love for Music

Diana, famously dubbed “The People’s Princess,” was a known music lover, with a particular fondness for bands like Duran Duran. However, she was also a fan of Michael Jackson and reportedly kept his albums Thriller and Bad on repeat. This admiration set the stage for their meeting, as she attended the concert with then-husband, Prince Charles.

Before the show, Michael, feeling both excited and nervous, had made a unique adjustment to his setlist. Concerned that his song “Dirty Diana” might offend the princess, he removed it from the show. When Diana inquired whether he would perform the song, Michael explained that he’d taken it out out of respect. However, to his surprise, she insisted that he go ahead with it. Ultimately, Michael performed “Dirty Diana,” honoring her request.

Diana, Princess of Wales (1961 – 1997) meets singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. (Photo by Princess Diana Archive/Getty Images)

Shared Struggles in the Public Eye

Although they would only meet in person this once, their connection would continue beyond that night. Michael later recalled that they stayed in contact through late-night phone calls, during which they would speak for hours about their challenges with the media and their shared love for their children.

“We were very close,” Michael shared with German media in 1999. “She would call me, usually very late, to talk about her children and her struggles with the press.” Michael’s then-wife, Lisa Marie Presley, reportedly grew jealous of these long conversations, even listening in from another room.

Though friends of Diana later denied that she shared her private number with him, Jackson’s former bodyguard, Matt Fiddes, confirmed the late-night calls, saying Michael saw Diana as one of the few people who could understand his life. Both endured relentless media scrutiny, sacrificing their privacy as they navigated fame.

A Mutual Dedication to Charitable Causes

Diana and Michael shared more than just personal struggles; they were both deeply committed to charitable work. At the time of their meeting, Michael had donated a substantial amount to British charities, including $188,000 to the Prince’s Trust and $126,000 to Great Ormond Street Hospital. Both also had similar tastes in jewelry and often patronized England’s premier jeweler, Butler & Wilson.

Their shared commitment to humanitarian work and their similar life challenges fostered a unique kinship. Jackson’s former bodyguard believed that Michael’s admiration for Diana grew to something more profound, even describing him as “in love” with her, citing the deep understanding they shared of the pressures and sacrifices of fame.

Michael’s Heartbreak Over Diana’s Tragic Death

Their friendship endured until Diana’s sudden death in 1997. The news struck Michael profoundly—he was reportedly so shocked that he fainted upon hearing it. He was scheduled to perform a concert on his HIStory tour in Belgium but canceled the show, overwhelmed by grief.

Michael later paid tribute to Diana at his next performance, dedicating his concert to her memory. “In my heart, I was saying, ‘I love you, Diana. Shine on forever, because you are the true princess of the people,’” he shared with fans. Although he did not attend her funeral, he honored her privately by attending a memorial service in Los Angeles, where he expressed his love and respect for her life and legacy.

In interviews following her death, Michael spoke fondly of Diana, often reminiscing about their shared connection. “She was one of the sweetest people I’ve ever known,” he said in 2003. He expressed how they bonded over the cruelty of the media and found comfort in each other’s understanding of how challenging and isolating fame could be.

Diana, Princess of Wales (1961 – 1997) meets singer Michael Jackson backstage at Wembley Stadium in London, before a concert by Jackson in aid of the Prince’s Trust charity, July 1988. (Photo by Princess Diana Archive/Getty Images)

The Enduring Legacy of Diana and Michael’s Friendship

Both Diana and Michael left the world too soon, and under tragic circumstances. Their brief yet meaningful connection highlights the often unseen struggles of fame and the rare friendships that emerge from shared experiences in the public eye. That one photo of Diana and Michael at Wembley Stadium, seemingly a simple moment, stands as a testament to their brief but powerful friendship—a connection that neither could have foreseen but both clearly valued deeply.