Michael Jackson & Diana Ross: The Untold Love Story

The connection between Michael Jackson and Diana Ross has long captivated fans. Their relationship, which began with a spark in Jackson’s childhood, blossomed into a bond that, according to his family and those close to him, he carried until his final days. This article delves into the journey of their complex connection, marked by love, admiration, and hints of unrequited passion.

The Early Connection and a Blossoming Friendship

Michael Jackson first encountered Diana Ross at just ten years old. In 1969, when the Jackson 5 auditioned for Motown Records, Diana was already a superstar, transitioning from her fame with The Supremes. Ross, who was one of Motown’s brightest stars, took young Michael under her wing, giving him a glimpse into the world of show business. In a media-fueled narrative, it was implied that Ross had “discovered” the Jackson 5, although this was later debunked. The myth, however, enhanced the allure of their relationship, intertwining Ross’s legacy with Jackson’s early fame.

When the Jackson family moved to Los Angeles, Michael moved in with Diana temporarily. His affection for her deepened, and he would teasingly refer to her as his “girlfriend,” playfully guarding her from his brothers. This early infatuation set the stage for a relationship that evolved into an intense, lifelong attachment.

The Wiz and Their Collaborative Flirtation

In 1977, Jackson and Ross co-starred in the film The Wiz, a reinterpretation of The Wizard of Oz, where Michael played the Scarecrow and Diana starred as Dorothy. Their on-screen chemistry was bolstered by a close friendship that thrived on flirtation and admiration. Ross was instrumental in bringing Jackson onto the project, using her influence to secure his participation. Reports indicate that Ross, then 33, needed a big-name co-star to justify her casting as Dorothy, a role typically reserved for younger actresses.

While filming in New York, their camaraderie was evident. They were often seen attending parties at the famous Studio 54, and even shared an apartment. One of Ross’s assistants recalled a morning when they were trying to locate both stars, only to discover they were together, with Diana reportedly having spent the night. Although Ross’s assistant jokingly confirmed that Jackson wasn’t “gay” after a conversation with her, this fueled rumors about their relationship. Jackson himself left the mystery intact, cryptically saying, “You’d have to ask her that.”

A Love Complicated by an Age Gap

Michael Jackson’s infatuation with Ross extended into his adulthood, yet Diana saw their 13-year age gap as a barrier. Ross, being an ambitious public figure, was cautious about the optics of their relationship. She feared that the world might misinterpret their connection, considering her motherly stance toward Jackson during his early years. Although Jackson dreamt of a more serious relationship, Ross drew clear boundaries, and the public perceived them as a maternal duo, as evidenced by their red-carpet interactions. In 1981, on the Oscars red carpet, Ross famously joked, “He’s going to play my son,” playfully highlighting their age difference.

Despite Ross’s stance, Jackson held onto his feelings, viewing their relationship as unique and meaningful. He once said, “Diana Ross is everything you could wish for, I love her. I hope she marries me.” His sentiment remained steadfast, even as Ross subtly distanced herself.

Heartbreak and Unrequited Love

Jackson’s devotion to Ross faced a harsh reality in 1985, when Ross met and married her second husband, Norwegian businessman Arne Næss Jr. Jackson was reportedly devastated and even canceled his attendance at her public wedding. While Jackson was supportive of her happiness, he admitted that he was hurt and a bit jealous, struggling to let go of his deep-seated affection.

In 1986, the American Music Awards saw Jackson arriving with actress Elizabeth Taylor, appearing distant towards Ross. The event hinted at a shifting dynamic, as Jackson seemed to use Taylor as a shield to cope with Ross’s marriage. He performed on stage for We Are the World, but his interaction with Ross was visibly cold, marking a low point in their friendship.

Expressions of Love in Music

Jackson’s feelings for Ross found a voice in his music, and several songs are rumored to be about her. “Remember the Time” from his Dangerous album is believed to reflect on his admiration for Ross, with his brother Jermaine sharing that it was inspired by “the one great love that, as far as he was concerned, escaped him.” Similarly, “Dirty Diana” from Bad, although primarily about groupies, has been speculated to contain elements of Jackson’s frustration over his unrequited love for Ross.

These musical tributes suggest that, even if Ross was out of reach, Jackson’s love for her was woven into his art, immortalizing her impact on him.

A Long-Lasting, Complex Bond

Though Jackson’s romantic hopes were dashed, he continued to cherish his connection with Ross. When Jackson was hospitalized in 1995, his then-wife Lisa Marie Presley reportedly had to leave his hospital room to make space for Ross, emphasizing her special place in his heart. Jackson’s dedication was evident when he created a shrine of mementos and photos dedicated to Ross, showcasing his admiration and affection.

In a 1991 interview, Ross herself admitted, “When he wants to see me, he sees me; when he doesn’t, he kind of closes the door.” Her words underscored the elusive nature of their connection—a bond that was deeply meaningful, yet ultimately evasive.

A Final Testament of Friendship

Jackson’s affection for Ross was so enduring that he included her in his will. After his death in 2009, it was revealed that he wished for Ross to become the guardian of his children if his mother, Katherine Jackson, was unable to do so. This act symbolized Jackson’s faith in Ross’s guidance and love, showcasing the maternal role she had played in his life. By honoring Ross in his will, Jackson confirmed that, despite the unfulfilled romance, her presence had been a source of comfort and strength for him.

Remembering an Unconventional Love

The story of Michael Jackson and Diana Ross speaks to the complexities of love, friendship, and admiration that defy conventional boundaries. While Jackson’s feelings for Ross may have been deeper than hers for him, their relationship transcended a mere crush or friendship. It was a connection that left a lasting impact on both their lives. Jackson’s love for Ross is a testament to his loyalty and devotion, a symbol of the emotional depth that made him a legendary figure. Theirs is a love story marked by warmth, loyalty, and a wistful sense of what could have been.