There is one spectacular photo of Princess Diana and Michael Jackson that has always stayed in my mind.
At first glance, it seems like just a moment captured between two legends. But if you delve deeper, their story turns out to be much more interesting.
Did you know that their connection was deeper than it may seem at first glance?
Neither Princess Diana nor Michael Jackson need any introduction – their iconic status speaks for itself.
It’s no surprise that these two incredible personalities once met. But few would have guessed that their meeting would lead to more than just a polite conversation….
They only met in person once
First of all, Princess Diana, known as the ‘People’s Princess’, was a huge music fan. Her favourite band was reportedly Duran Duran – in the 1980s, she adored their songs.
However, she also had Michael Jackson albums in her record collection, indicating her love for his work as well. For example, she is rumoured to have listened to Thriller and Bad on repeat.
Michael Jackson’s music was the reason for their only meeting on 16 July 1988.
On that day, she and her then husband, Prince Charles, attended a Bad Tour concert at Wembley Stadium. It became their first and last face-to-face interaction.
‘She told me she was honoured to meet me,’ Jackson told Barbara Walters in a 1997 interview.
Michael recalled that before shaking hands with Diana, he felt an incredible excitement – a tension that can even be felt in the photos from that day.
There was a reason their first meeting seemed a little awkward and tentative.
He cut the song ‘Dirty Diana’ from the concert
The fact is that Michael decided to exclude the song ‘Dirty Diana’ from the concert programme, fearing that it might offend the princess. This composition about rock bands (‘groupies’ – fans who follow musicians) seemed to him inappropriate for performance in the presence of a representative of the royal family.
‘I took it out of the show in honour of Her Highness,’ Jackson told Barbara Walters in 1997.
Diana’s reaction to meeting Michael
However, the gesture did not please the princess at all.
During a meeting before the concert, Diana asked Michael if he was going to perform ‘Dirty Diana.’ When he replied that he had removed it from the programme because of her presence, she insisted that he bring the song back and perform it. Michael eventually followed her request and included the song in the concert set list.
Jackson clearly admired Diana and treated her with the utmost respect.
‘I thought the princess was just wonderful,’ he admitted to reporters.
Knowing how much she adores her sons, Michael presented Diana with two miniature concert jackets for Princes William and Harry.
Diana, an avid pop music fan, reportedly danced the entire concert while Prince Charles remained seated in his seat.
Was Michael Jackson in love with Diana?
Few expected that their first meeting in 1988 would lead to such a strong emotional connection.
‘We were very close,’ Jackson told German media in 1999. – ‘She used to call me a lot … I was still married to Lisa Marie [Presley] at the time. Diana used to wake me up late at night … mostly after three o’clock in the morning! And then she’d keep me on the phone for hours. She talked mostly about her kids and the press.’
Michael claimed that Diana could talk to him on the phone for hours.
‘Lisa Marie was terribly jealous. She would go into another room, pick up the phone and eavesdrop,’ he added.
However, it is impossible to confirm whether the late-night calls were indeed true. According to Diana’s friends who spoke to The Express, Jackson allegedly never had her private number. If he called Kensington Palace, staff were instructed not to connect him to the princess.
But what is certain is that they both went through similar ordeals and shared a passion for the same charitable causes.
Both were dedicated to charity
Diana and Michael Jackson were both actively involved in charity work. At the time of their first meeting, Jackson, known for his humanitarian work, had already donated $188,000 to the Prince’s Trust, a youth-focused charity, as well as $126,000 to the children’s fund at Great Ormond Street Hospital in London.
They also had similar taste in jewellery. Both were clients of Butler & Wilson, one of Britain’s leading jewellers.
But was there more than friendship and shared values between them?
Was Michael Jackson in love with Princess Diana?
Jackson’s former bodyguard, Matt Fiddes, claimed that the late-night phone calls did happen, and even claimed that the singer was ‘in love’ with Diana.
Fiddes, who worked with Jackson for ten years, said:
‘[Michael] felt she was the only person in the world who could understand his life: the inability to go out, the scandalous rumours in the press… The constant invasion of privacy, the lack of any privacy, the harassment of his children…’
How did Michael Jackson react to Diana’s death?
Diana and Michael had one other thing in common: the paparazzi stalking. For years, they were among the most photographed people in the world.
Diana was constantly in the spotlight, and her controversial image within the royal family invariably attracted the interest of tabloids and reporters. Similarly, Michael Jackson, with his transformed appearance and eccentric lifestyle, was an easy target for the media.
Their friendship is said to have lasted until Diana’s tragic death in 1997.
When Michael learnt of her death, he was shocked. According to The Express, the news shocked him so much that he fainted and had to be revived with ammonia.
He also postponed his concert as part of his HIStory tour. Jackson was due to perform in front of 60,000 people in Belgium, but organisers said the singer was so grief-stricken he was unable to take to the stage.
Ironically, Diana passed away just two days after Michael’s 39th birthday.
Farewell to the Princess
Days after the tragedy, Michael returned to the stage and dedicated the concert to Diana’s memory.
He said:
‘In my heart I was saying, ‘I love you, Diana. Shine. And shine forever, because you are a true folk princess.”’
However, Michael did not attend Diana’s funeral in London. Instead, he attended a memorial service in Los Angeles, where he told reporters:
‘I came to honour my friend who is no longer here… I love her.’
Dressed in a black suit, with a black fedora and red armband, Jackson arrived at the church surrounded by bodyguards. He was one of thousands of guests at the service.
Michael Jackson on Diana after her death
Years later, Jackson warmly remembered Diana on more than one occasion.
In 2003, he spoke out about her again:
‘She was one of the kindest people I’ve ever known because we understood each other.’
‘We shared one common problem – the press. I don’t think anyone was harassed the way she and I were. We had a special relationship: we’d call each other at night… Just complaining, crying into each other’s phones about how hard it was, how cruel the tabloids could be.’
These words clearly show that Diana and Michael Jackson were indeed bonded by more than just fame. They found support in each other in dealing with the media attention, which often turned into real harassment.
It is fascinating to watch the moments where Princess Diana and Michael Jackson are together. Unfortunately, they were both gone too soon and under strange circumstances. The photographer who captured this iconic moment probably didn’t even realise the historical significance of what would become Diana and Michael’s only meeting.
But looking back, this photo symbolises the first timid steps of a bond that has only grown stronger over time.
