Michael’s love for Diana started off as a childhood crush but developed into a teenage infatuation. His brother, Jermaine, mentioned in his book: ‘They only became close when Michael came of age. I know Michael has always loved Diana, from when he was a small boy, he knew he wouldn’t be able to act on his love for her until he became an adult’.
By the late 1970s, Diana Ross & Michael Jackson flirted wildly in public and numerous reports at the time speculated whether the two were having a romance. But was there any truth to this? Did Michael Jackson’s obsession with Ross extend into a full-blown affair? Or did the two stars use the speculation to benefit both their careers.
Michael Jackson first met Diana Ross at age 10, when he and the other four members of the Jackson Five auditioned for Motown Records, in which Diana was the labels most shining star. Paving her own career outside her Supremes fame of the 1960s, Diana first saw Michael and his brothers performing for a charity show. After that, Diana met all the Jackson 5 and ensured that she would do all that she could in order to help them in their career. Although untrue, what was fed to the media was that Diana Ross discovered the Jackson 5 and used her connections to propel them into superstardom.
Michael often talked about Diana Ross, and his love for the Supremes even before fame. When he and his brothers signed to Motown and the family were looking for a place in Los Angeles, Michael moved in with Diana. Michael used to tease his brothers, call her his ‘girlfriend’ and wouldn’t let anyone near her.
In 1977, Michael Jackson accepted the role as the Scarecrow in the film adaptation of ‘the Wiz’. This was largely due to his long-time friend, Diana Ross, who was also named to play Dorothy. However, it was speculated that Ross would only get the part if she could get Michael Jackson, a teen idol at the time, to take part in the film as well; as at 33 she was considered too old for the part. Pauline Kael, a film critic, described Ross’s efforts to get the film into production as “perhaps the strongest example of sheer will in film history.”
Michael Jackson’s mother, Katherine, once said “when Diana Ross was named to play Dorothy, Michael had further incentive to land a role in the movie; he’d been in love with her ever since he and his brothers had been her house guests. “You’re not pretty until you start looking like Diana!” he would tease LaToya and Janet.”
Jackson Biographer, J. Randy Tarraborelli, recounted that in 1977 while on The Wiz shoot, Michael Jackson and Diana Ross would regularly go out at night attending parties and New York’s Studio 54 nightclub. One of Diana’s assistants said he had been trying to get hold of both of them all morning as they were late for filming. Eventually they got hold of them on the phone and was surprised to find they were in his apartment and that she had apparently spent the night there.
Later on, during the shoot Diana was apparently overheard talking to some girlfriends of hers and said to one of them, “well, I’ll tell you one thing, Michael definitely isn’t gay.” When this assistant asked Michael if anything had happened between them, Michael said, “you’d have to ask her that,” and when he asked Diana, she told him he needed to ask Michael.
This flirtation between Michael Jackson and Diana Ross would continue for years to come, as Michael’s infatuation grew. But Diana never took the relationship seriously because of their 13-year age gap. Although this was never an issue for Michael, Diana on the other hand could not overcome the taboo of the age and their association when Jackson was a child. She was fearful of how this would impact on her public image and thus her career, and Diana Ross was a fiercely ambitious woman.
After a photo session with Diana Ross and photographer Todd Gray, Gray showed Jackson proof sheets and Jackson ordered two large prints of every picture. The photographer was blown away. ‘Two of every single one? That’s about 144 prints’ Michael answered, ‘Yes, I can count. I want one set for myself and one for Diana. Todd, this is magic.’
During Diana Ross’s 1981 special, Michael Jackson was featured heavily. They performed together three times, and Michael was the only other person who had their own performance other than Diana Ross herself. While being introduced, Diana called Michael her baby and they hugged several times. The special also included a mini interview between the two where they flirted and called each other sexy.
Diana Ross said in Ebony that same year, ‘I’m crazy about Michael and I love him a lot. He’s been my inspiration. He’s a very gentle, wonderful human being, one of the special ones in this universe, and I don’t even know if he knows how special he is. So, whenever I can be around him, I like it. His aura is only about love.’
Diana Ross’s vivacious character and affection towards Michael allowed fans to misconstrue it as sexual. Diana’s personality was infectious, and she was flirty with all men in public, including Michael. It’s one of the tragedies of Michael Jackson that he dwelt on this romantic obsession and did not let it go. Jackson even erected a shrine dedicated to the love of his life in his family home, with photographs and mementos.
However, Diana wasn’t interested in Michael and made several attempts to soften the blow for him. The public saw her and MJ as mother and son, this is demonstrated while on the red carpet with Michael at the 1981 Oscars she said, “he’s going to play my son”, as a result they burst out laughing and walked away.
But even with Diana’s hints and gentle let downs, in Michael Jackson’s naïve mind, he and Diana were in a relationship and he had hopes that they would ultimately be together. In 1983, Michael Jackson once said in an interview, ‘Diana Ross is everything you could wish for, I love her. I hope she marries me. She always tells me her most private secrets. That’s the kind of relationship we have. It goes on forever’.
Michael Jackson was devastated when Ross met her second husband, Norwegian shipping magnate Arne Næss Jr., in 1985. The two married the following year and Michael Jackson apparently cancelled his attendance to the public wedding at the last minute. ‘When I heard Diana Ross was getting married, I was happy for her because I knew it would make her very joyous. Still, it was hard for me, because I had to walk around pretending to be overwhelmed that Diana was getting married to this man I’d never met. I wanted her to be happy, but I have to admit that I was a bit hurt and a little jealous’.
During 1986’s American Music Awards, Michael showed up halfway through the show, with a suitable replacement for Diana Ross in the form of Elizabeth Taylor. It was noted how Michael Jackson appeared visibly upset and cold towards Ross during the show, in which he reluctantly celebrated the success of USA Africa’s ‘We are the World’ charity single.
Michael Jackson went on to write several songs about Diana Ross and their relationship while recording material for his Bad and Dangerous albums. Songs which were released included, 1992’s ‘Remember the Time’, in which Jermaine, Michael’s brother, wrote that ‘the song was, as Michael told me, written with Diana Ross in mind; the one great love that, as far as he was concerned, escaped him’’.
Michael also released ‘Dirty Diana’ in 1987 on the Bad album. Many fans speculating that although the song was about groupies, it was also a dig at Diana Ross while he was angry at her for leading him on and then getting married to another man.
Ross’s marriage however was not happy in spite of two sons. Diana and Arne were married yet they lived on separate continents. Diana mentioned in interviews that she couldn’t live in Norway because it was cold and dark and didn’t want to move away from her older kids, family and career in the US. Diana Ross secretly saw Michael Jackson even during her pregnancies. He was devastated and broken-hearted but was still under her spell, however. ‘’I’ve always loved Diana and i always will’’ he wrote in his autobiography, Moonwalk.
But as the years went by, Michael’s interactions with Diana became more infrequent as she focused on family life and he extensively promoted and toured around the World. In 1991, Diana Ross told the Rock Hill Herald that ‘when he wants to see me, he sees me; when he doesn’t, he kind of closes the door. There’s no reaching him, there’s no finding him, there’s no anything. He’s just this illusive love out there’.
Although Diana always had a place in Michael’s heart, he called her his world when she visited him in hospital in 1995. He had his then wife, Lisa Marie Presley, literally thrown out of his room in preparation for Diana’s arrival in which he lavished her with affection and gifts. After Michael Jackson’s death in 2009 and many years since they had a close relationship, Diana Ross was mentioned in his will, stating that he would like to leave his children with her in the event of his mother’s death. This act, honouring her as the great mother she was to her children and knowing in death she would be best to guide his own. But also honouring their lifelong friendship, the lasting bond they developed over the years and a last reminder of the special place she always had in his heart.