Michael Jackson and Princess Diana lived in completely different worlds, yet both knew what it felt like to have almost every movement photographed and analyzed. They met face to face only once, but Michael later said something much more private developed afterward. Diana would telephone him late at night, sometimes after 3 a.m., and their conversations could continue for hours.
According to Michael, Diana spoke with him about her children, the press and the pressure surrounding her life. He believed they understood each other because both knew what it was like to feel hunted by photographers and tabloids. Michael later said Diana could discuss those feelings with him because he had lived under intense public attention since childhood.
Michael Jackson Talks About Princess Diana After Her Death
Their friendship began after Diana attended Michael’s Bad Tour concert at Wembley Stadium on July 16, 1988. Michael had actually removed “Dirty Diana” from the show because he worried performing a song with her name might offend her. Diana surprised him by asking whether he planned to sing it and encouraged him to put it back into the show.
They apparently never met in person again, but Michael said the phone friendship continued. Years later he recalled Diana waking him late at night and keeping him on the telephone while they discussed children and the press. Former bodyguard Matt Fiddes also said Michael felt Diana was one of the few people who could truly understand what constant intrusion into private life felt like.
The 3 A.M. Phone Calls Between Michael Jackson and Princess Diana
This newer 2026 video is a particularly relevant continuation because it focuses directly on those private 3 a.m. conversations. It traces their friendship from the Wembley meeting through the late-night calls and Michael’s reaction when Diana died, adding context to why two of the most photographed people in the world apparently found comfort talking to each other when almost everyone else was asleep.
When Diana died on August 31, 1997, Michael postponed his scheduled HIStory Tour concert in Belgium. He later told Barbara Walters that the news devastated him, and when the concert was eventually held he dedicated part of the show to Diana. Michael Jackson would go on to be remembered for Thriller, “Billie Jean,” the Moonwalk and performances seen around the world, but this friendship revealed something fame could not provide: another person who understood what it cost to be watched everywhere you went. Watch the videos to hear Michael speak about Diana himself and discover why their unusual friendship continued long after that single meeting.