Diana Ross and Michael Jackson: A Friendship Shrouded in Mystery

It’s hard to find stars more iconic than Diana Ross and Barbra Streisand, but both divas have faced criticism in recent years for their comments regarding Michael Jackson. As calls to boycott Jackson’s music grow louder, Diana Ross, the legendary Motown diva, has finally opened up about her long and complicated relationship with the King of Pop. Now 80 years old, Ross sheds light on the highs and lows of their friendship, which has long been the subject of speculation.

Diana Ross first met Michael Jackson when he was just 10 years old, auditioning with the Jackson 5 for Motown Records. At the time, Ross was Motown’s biggest star, having already achieved fame with The Supremes in the 1960s. Their initial meeting sparked a connection that would last for decades.

While their early relationship was kept largely private, the media fueled stories that Ross “discovered” the Jackson 5 and used her influence to help them rise to fame. Though the facts of their history are less dramatic, there’s no doubt that Ross played an instrumental role in the Jackson 5’s success.

As a young boy, Michael Jackson looked up to Ross not just as a mentor, but as an icon. He was enamored with her elegance, beauty, and talent, often teasing his siblings by calling Ross his “girlfriend.” While this was playful at first, his feelings for her deepened as he grew older.

According to Jermaine Jackson, Michael’s brother, Michael developed a serious crush on Ross, and this infatuation only grew as he matured.

Diana, 13 years his senior, saw Michael as a dear friend and a younger brother. While she was flattered by his admiration, she maintained a platonic view of their bond. Still, Michael’s feelings persisted, and he reportedly became obsessed with the idea of a romantic relationship with Ross, even going as far as building a shrine to her in his home.

Throughout the late 1970s and early 1980s, their public interactions fed speculation about a potential romance. In 1977, Jackson agreed to play the Scarecrow in The Wiz largely because Ross, who was cast as Dorothy, persuaded him to join the project.

The two became inseparable on set, often attending New York parties together at Studio 54. Biographers reported that the pair would sometimes be unreachable in the mornings, adding fuel to rumors of an affair.

Despite the media frenzy, both Ross and Jackson always denied a romantic relationship. In public, Ross even referred to Jackson as her “baby” and later joked that he was “like a son” to her. Still, Michael’s feelings never wavered, and in a 1983 interview, he openly admitted that Diana represented all of his dreams, saying he had “strong emotions” for her.

Their close friendship took a hit in 1985 when Ross married her second husband, Norwegian businessman Arne Naess Jr. Michael was heartbroken and even refused to attend the wedding, despite their deep bond.

Although he wished Ross happiness, he later admitted feeling a mixture of sadness and jealousy. Their once-close relationship began to drift apart, with Ross focusing on her family and Michael diving deeper into his career.

In his music, Jackson often hinted at his unresolved feelings for Ross. His song “Remember the Time,” released in 1992, was believed to be about her. Another track, “Dirty Diana” from the 1987 album Bad, was rumored to be a reflection of his disappointment and anger toward Ross for marrying someone else.

Despite the ups and downs, Michael Jackson never stopped caring for Diana Ross. Even after their contact became less frequent, Jackson held Ross in high regard. In 2009, when Jackson passed away, his last will and testament revealed just how deep their connection had been: Ross was named as a potential guardian for his children if his mother, Katherine Jackson, was unable to care for them. This gesture showcased the trust and affection he had for Ross until the very end.

Born on March 26, 1944, in Detroit, Michigan, Diana Ross grew up in a Baptist family as the second of six children. Her journey to superstardom began in 1958 when she joined The Primettes, an all-girl group that later became The Supremes.

With hits like “Where Did Our Love Go” and “Baby Love,” The Supremes dominated the charts, becoming one of Motown’s most successful acts.

Ross’s ambition led her to a solo career in the 1970s, where she continued to break records and set trends in the music industry. Her powerful vocals, glamorous persona, and undeniable stage presence cemented her status as a living legend.

The relationship between Diana Ross and Michael Jackson remains one of the most fascinating and enigmatic stories in music history. From their early days at Motown to their later years, their bond was marked by love, admiration, and, at times, heartbreak.

While rumors of romance were never confirmed, their mutual respect and affection were clear, leaving a lasting legacy in the world of music and pop culture.

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