What Really Happened Between Brooke Shields And Michael Jackson?

Brooke Shields and Michael Jackson both experienced the pitfalls of child superstardom. Age-wise, Brooke hadn't even reached the double digits when she played a prostitute in the controversial film "Pretty Baby," while Michael joined his family's singing group, the Jackson 5, at age 5.

The actor/model and the singer were both managed by controlling parents who pushed them into the spotlight. When Michael appeared on "The Oprah Winfrey Show" in 1993, he recalled how his father, Joe Jackson, demanded perfection from his "golden child," revealing that Joe beat him and terrified him so much that he would become physically ill. As for Brooke, her mother, Teri Shields, meticulously micromanaged her career. Teri's presence loomed so large in her daughter's life that Brooke told The Guardian, "I was in a cocoon with my mom. You know, we were one summer away from Grey Gardens."

Throughout his life, Michael gravitated toward other celebrities who knew what it was like to be a child star, with some of his famous friends including Elizabeth Taylor and Macaulay Culkin. He and Tatum O'Neal dated, per The Guardian, and Michael also connected with Brooke on a deep level. However, they had conflicting views on the exact nature of their relationship. 

In recorded conversations with Rabbi Shmuley Boteach, Michael Jackson reminisced about Brooke Shields introducing herself to him at the Oscars. "That was one of the loves of my life," he said. "I just wished she loved me as much as I loved her." Jackson revealed that he was already a huge fan of Shields when they met and had her photos plastered all over his room. So, after Shields asked him to dance at an afterparty, he was on Cloud 9. "I was up all night, singing, spinning around in my room, so happy," he gushed.

On the "Jim and Sam Show," Shields said she was 13 when she and Jackson met. While Jackson claimed that he and Shields dated, she said that the two of them were simply really good friends who bonded over their shared experiences as child stars and spent a lot of time together. "I think that there was an arrested development," she said of Jackson. "We acted like little kids."

Speaking to People, Shields painted a more vivid picture of their childlike friendship. "We joked about how silly people were and watched movies and ate candy," she recalled. However, she told Rolling Stone that Jackson wanted something more, revealing that he even proposed to her on multiple occasions. "I would say, 'You have me for the rest of your life, you don't need to marry me," Shields recalled, theorizing that Jackson simply didn't want to lose her friendship.

On "Watch What Happens Live," Brooke Shields told Andy Cohen that Michael Jackson asked to be her daughter Rowan's godfather when she was born in 2003. "I thought, 'Oh my god, that's so sad that he wanted to do that,'" said Shields. "I had to deny him that." The two friends didn't spend as much time together when they got older, but on the "Jim and Sam Show," Shields said Michael remained a supportive presence in her life throughout the remainder of his own, revealing that he even sent her flowers when she was struggling with postpartum depression.

When Michael died in June 2009, his mother, Katherine Jackson, reached out to Shields and asked her to speak at his memorial. During her speech, Shields reflected on some of the happy memories that she and Michael made together, like attending Elizabeth Taylor's wedding. Shields also attended her friend's funeral and confronted his father afterward. "I said, 'You know what? You never liked me. You never even pretended to like me. I never liked you. You always were mean,'" she recalled saying to a flabbergasted Joe Jackson before thanking him for his son.

But when Shields ran into Michael's daughter, Paris Jackson, at a Calvin Klein show years after the singer's death, their encounter was anything but frosty. On "Watch What Happens Live," Shields recalled, "[I] said, 'I really miss your dad, and she looked at me and she held me and she goes, 'Me, too.'"