Sheryl Crow Reflects on Her ‘Surreal’ Journey with Michael Jackson

In a candid and emotional reflection, Sheryl Crow recalls the unforgettable experience of touring with Michael Jackson and the lasting impact it had on her life. Moving to Los Angeles with little more than a demo tape and big dreams, Sheryl unexpectedly found herself embarking on a life-changing journey as part of Michael Jackson’s legendary tour.

It all started when Sheryl, fresh out of Missouri, auditioned for the “Bad” tour. A seemingly harmless, young schoolteacher in modest clothes, she captured Michael’s attention with her down-to-earth charm. “I just moved here, and I’d sure like to go on the road with you,” she recalls saying, which led to her joining the tour, much to her surprise. The next thing she knew, she was performing in front of 75,000 people in Tokyo, an overwhelming yet transformative experience that marked the beginning of her extraordinary adventure.

The journey with Michael Jackson was nothing short of surreal. Crow’s life shifted from being a session singer to touring the globe, visiting Japan, Australia, and Europe, seeing the world through the eyes of musicians from diverse backgrounds. “It was just a crash course on joining humanity,” she says, describing the bond she formed with her fellow band members. In addition to the exhilarating sense of global adventure, there was also the honor of witnessing Michael Jackson’s unparalleled artistry.

Despite being surrounded by the immense fame and adoration of Jackson, Sheryl acknowledges the complexity of their relationship. Michael, famously reclusive, took nearly nine months before learning the names of his backup singers. Yet, in her eyes, he was an enigmatic mix of innocence and brilliance. “He had a playful side, a childlike quality,” she shares. “He was a shrewd businessman but still retained the wonder of a child. It was like he could channel something divine when he performed.”

Behind the scenes, Michael’s behavior sometimes veered into the bizarre, including moments like his playful interactions with his pet chimpanzee, Bubbles. “We’d be in the same quick-change area, and he’d throw grapes at me or make fun gestures,” Sheryl remembers. “He’d laugh like a little boy, and I would just have to remind myself that this was Michael Jackson, the biggest pop star in the world.”

Yet, their connection wasn’t without controversy. Sheryl was swept into tabloid rumors about a supposed affair with Michael, even being labeled as the woman he allegedly paid $2 million to have his baby. “I remember walking into a drugstore and seeing my face on the cover of the National Enquirer,” Sheryl laughs now, though at the time it was jarring. “It was bizarre, but it also highlighted how little people truly understood the truth of who Michael was.”

As the tour wrapped up, Sheryl returned home to a world forever changed. The naive, schoolteacher version of herself felt far removed from the woman who had just spent 18 months traveling the world with Michael Jackson. The public’s fascination with her role as his backup singer added pressure to her burgeoning music career, with many pushing her to make pop music like Madonna or Paula Abdul. But Sheryl had other plans, opting to carve her own path in music, rooted in authenticity and soul.

Years later, after Michael Jackson’s tragic death at 50, Sheryl reflects on the deep sense of loss. “It’s like a death in the family,” she says, still processing the complexity of Michael’s life. Her thoughts also turn to the allegations of abuse that arose after his death, acknowledging the painful reality that many people around him, including himself, were affected by a toxic environment. “There was a network of people that allowed so much to happen. It’s tragic,” she admits, voicing her sadness over the whole situation.

Sheryl, having experienced the intensity of both the fame and the darker sides of the music industry, reflects on her own journey with mixed emotions. “Being in the music business, especially as a woman, I faced a lot of sexual harassment. It’s part of a bigger problem,” she reveals. “But I’ve healed, and I’m no longer that naive girl who thought that good things always happen to good people.”

Her time with Michael Jackson was not just a career milestone, but a personal reckoning with the challenges of the industry. Today, Sheryl Crow is a seasoned artist who has learned not only to navigate the pressures of fame but to create music that is true to herself, far beyond the shadow of the King of Pop. “It was a strange introduction to show business,” she says, but one that shaped her in ways she could never have imagined.