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Over the years, Jackson has had his obsessions with "it girls," including Elizabeth Taylor, Brooke Shields and Princess Diana. But Ross was always his idol. The two became close after Jackson signed on with Motown as a child.
When Jackson made his solo debut in 1971, he did it on one of Ross' TV specials.
In a 1981 Diana Ross TV special, Ross brought out Jackson's shy demeanor, teasing him about being "very sexy."
"You are embarrassing me," he replied, laughing.
They were so close, in fact, that some have even speculated that Jackson's plastic surgeries were done to make him look like Ross.
"Whether that was purposeful on his part has never been explained by M.J. when he was alive or anyone close to him. Certainly the parallel in their appearance was marked," said J.D. Heyman, assistant managing editor of People magazine.
Ross has yet to speak publicly on the death of her good friend, but she issued a statement shortly after he died. "I can't stop crying, this is too sudden and shocking. I am unable to imagine this," she said. "My heart is hurting. I am in prayer for his kids and the family."
Jackson's infatuation with Ross began when they first met at Motown. She was the glamorous star of the Supremes, he was a 9-year-old performing prodigy.
Though it's been said that she discovered Jackson and his brothers, the Jackson 5, it was actually Gladys Knight and the Pips, another Motown act, who first saw them perform at the Regal Theater in Chicago and tried to get them an audition with Motown founder Berry Gordy. Motown artist Bobby Taylor got them the audition. But when the press release announcing the hot new group came out in 1969, it said Ross, the label's biggest star, had discovered the group while on tour.
Jackson played along with it. In an interview at the age of 10, he said, "I thought I was going to be an old man before being discovered, but along came Miss Diana Ross to save my career."
Jackson idolized Ross, according to biographer J. Randy Taraborrelli, who has written books about both superstars.
In his book, "Call Me Miss Ross," he wrote that Ross said, "I was older. He kind of idolized me and wanted to sing like me."
Some would say he even wanted to be her.
Taraborrelli wrote about one instance in 1986, when Jackson visited Ross backstage at Caesar's Palace in Las Vegas. When she returned to her dressing room, Jackson was putting on her makeup, transforming himself into Ross.
The writer also said Jackson once demanded that a chauffeur driving him around Beverly Hills that he address him as "Miss Ross."
In his autobiography "Moonwalk," Jackson called Ross "my mother, my lover and my sister all rolled into one."
Taraborrelli has said there was no sexual relationship between the two.
Nonetheless, in "Call Me Miss Ross," Taraborrelli wrote that Jackson was heartbroken when Ross got married for the second time to Naess. Jackson did not attend the wedding, telling Taraborrelli, "I was jealous, because I've always loved Diana Ross and always will."
Ross may have felt more motherly toward him. When Jackson moved to Los Angeles at the age of 9 to continue his recording career with Motown, he lived with Ross for a time.
The two stars shared a lot in common. Both started at Motown and became worldwide pop stars. Both earned diva reputations for their outsized lifestyles. And both were accused of selling out and turning their backs on their black heritage.
When Jackson collapsed during a rehearsal for a cable TV concert in 1995, Ross rushed to his bedside at a hospital in New York.
Biographer Brown said he wasn't aware that Ross and Jackson were close in recent years, but the fact that he included her in the will, he said, "just reiterates that she was his idol."