Before she was a Grammy-winning solo artist, Sheryl Crow was a Missouri schoolteacher with dreams of breaking into the music industry. That dream took an extraordinary turn when, in 1987, she crashed a closed audition and landed a life-changing gig—singing backup for Michael Jackson on his Bad World Tour. Overnight, she went from classrooms to sold-out stadiums, sharing the stage with the world’s biggest star. But behind the glitz, their relationship was far more complicated than their on-stage chemistry suggested.

For 18 months, Crow performed “I Just Can’t Stop Loving You” with Jackson every night, playing the role of a sultry duet partner to perfection. Their playful stage interactions sparked rumors of a romantic affair, with tabloids even alleging Jackson offered her $2 million to have his child—claims Crow laughed off in jest. But while they appeared close on stage, Crow revealed in interviews that Jackson often kept his distance off it. “I don’t even think he knew my name for a long time,” she once said.

Still, Crow has fond memories of touring with Jackson—watching him perform “Human Nature” from the wings, laughing at his backstage pranks, and even visiting his hotel suite in Tokyo to watch movies with him and his pet chimpanzee, Bubbles. “He was otherworldly,” she recalled. “Watching him dance just feet away from me made me feel like I was witnessing something divine.”

But her time on tour wasn’t all magical. Crow later revealed that Jackson’s manager, Frank DiLeo, repeatedly sexually harassed her and threatened to derail her career when she refused his advances. “He said I’d never work again,” she stated. The trauma plunged Crow into a deep depression after the tour ended. Though Jackson eventually fired DiLeo, the damage was done.

Returning to Los Angeles broke and emotionally bruised, Crow spent months in a dark place. But eventually, she clawed her way back. Her 1993 debut album, Tuesday Night Music Club, included veiled references to DiLeo’s behavior. The songs “What I Can Do For You” and “The Na-Na Song” referenced the harassment directly, prompting DiLeo to sue—but he died before the case went to court.

Crow’s career soared. She won three Grammys in 1995 and earned her place among the music industry’s elite. Yet, despite being in the same circles, Michael Jackson never reached out. When they ran into each other at the Grammys, Crow believed he didn’t even recognize her.

When Jackson died in 2009, Crow mourned him publicly. She recalled how the ABC album was the first record she ever owned and how performing beside him had been a career-defining moment. She released a cover of “I Want You Back” the following year in tribute. “There will never be anyone like him again,” she said.

But her sentiments shifted again after the release of Leaving Neverland in 2019. Though she admitted she hadn’t watched the film, she voiced concerns about things she’d witnessed during the Bad tour—specifically questioning the decision of James Safechuck’s parents to let a child travel alone with a pop star. “I was around for things that were really strange,” she told The Telegraph.

Sheryl Crow’s time with Michael Jackson remains a mixture of reverence, trauma, and confusion. While she praises his genius, she also mourns the dark machinery behind his fame—a machinery that nearly crushed her before she found her voice.

Whether a muse, confidant, or collateral damage of megastardom, Sheryl Crow’s story offers a rare backstage pass into the life of Michael Jackson—at once magical and deeply flawed.