In 1987, a 25-year-old backing singer and aspiring songwriter from Missouri gatecrashed her way into the Los Angeles auditions for Michael Jackson’s first ever solo world tour. “Hi Michael, my name is Sheryl Crow and I just moved here,” she announced. “I’m a former music teacher and I would love to go on the road with you.”
A month later Crow was onstage at the Korakuen stadium in Tokyo, her ears filled with the deafening roar of 75,000 fans. It was the first of 123 concerts over the next 16 months, during which she performed in front of a staggering 4.4 million people. Each night Crow, wearing a bustier and voluminous Eighties curls, harmonised with Jackson and shared the limelight on songs like “I Just Can’t Stop Loving You” and “Man in the Mirror”. It should have been a dream come true.
“Naiveté is such a beautiful thing,” says Crow, now 59, a nine-time Grammy winner and one of the most successful artists of her generation. She is speaking on a video call from her home in Nashville, her bedroom walls behind her filled with the art and arcane curios she collects from around the American south. An acoustic guitar lies at rest on the antique couch by her bed. “It was incredible in every way, shape and form for a young person from a really small town to see the world and to work with arguably the greatest pop star,” she says. “But I also got a crash course in the music industry.”