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.”
As the tour progressed, tabloids around the world reported rumours that Jackson was falling for his “sexy backing singer” and even that he had offered her $2m to have his child. In Crow’s audiobook memoir Words + Music, released last September, she states her belief that these stories were most likely to have been planted by Jackson’s manager, Frank DiLeo, “to make Mike look like he was interested in women”.
In truth, it was DiLeo who was interested in Crow. He subjected her to sustained sexual harassment throughout the tour, promising to make her a star while threatening that if she refused, or told anyone, he would ensure her career was over before it had really begun. She had never spoken in detail about her experiences with DiLeo prior to Words + Music, but two songs on her 1993 debut album made reference to him: “What I Can Do for You”, written from the perspective of a powerful abuser, and the stream-of-consciousness “The Na-Na Song”, which includes the defiant couplet: “Frank DiLeo’s dong / Maybe if I’d have let him I’d have had a hit song”.
Having announced that her eleventh album, 2019’s Threads, would be her last, Crow has spent the pandemic at her 50-acre home – which includes a full-scale recording studio over the stable where she keeps her horses – reacquainting herself with these songs and with the rest of her formidable back catalogue. On Friday 18 June, she will perform an intimate solo show titled The Songs & The Stories, live-streamed to the world from the church she built in her backyard, during which she will play her music and offer insights into how and why it was written.
“It’s really interesting to go back and revisit some of this old stuff and the experiences that went along with it, and then to compare it with where we are now,” says Crow. “To be able to play that stuff about the long bout of sexual harassment I endured during the Michael Jackson tour and to talk about it in the midst of the MeToo movement... it feels like we’ve come a long way, but it doesn’t feel like we’re quite there yet.”
Words + Music, she adds, “was the first time I’ve ever talked about it and it felt really uncomfortable, but it felt, to me, so much more empowering to be able to talk about it and then play the music that was inspired by it. Isn’t that what music is really for? To help us work through whatever our experiences are, and hopefully for the collective to find their own situations in your music too?”
When the Michael Jackson tour ended in 1989, Crow returned home to her tiny LA apartment and fell into a lengthy period of depression. A high-powered attorney she’d hired told her she should have put up with DiLeo’s advances given what he could offer her. From the inside, the music industry didn’t look anything like she’d expected.
Enjoy unlimited access to 70 million ad-free songs and podcasts with Amazon Music Sign up now for a 30-day free trialSign up
“You move to LA thinking you’ve done all your homework,” says Crow, counting off the steps of her journey on her fingertips. “You’ve practised your whole life, you’ve listened to the greatest artists, you’ve played in coffee bars, and then you get out there and you learn: ‘Okay, this is how the music industry works: a corporation buys so many records. It puts you in the top 10. We take your publishing.’ It was disillusioning. I think when your dream bubble is burst you either go: ‘Okay, well, I’m going to forget that dream,’ or you do what I did, which was wallow in it for about a year, and then you pull your bootstraps up and you get back to work.”
In 1993, Crow’s then boyfriend Kevin Gilbert introduced her to a group of musicians who met every Tuesday at producer Bill Bottrell’s studio in Pasadena. After some productive early sessions, Bottrell agreed to produce a solo record for Crow, Tuesday Night Music Club, which was released in August that year with songwriting credits split among the group. The record received little fanfare until the release of its third single in April 1994, the irresistible “All I Wanna Do”. Surprisingly, it was a song Crow hadn’t initially wanted on the album. “Aren’t all the best songs the ones you go: ‘Nah, this one will never…’?” asks Crow with a self-effacing laugh. “I wish I knew what made for a hit song because I would just do that every day and buy big houses everywhere, but I didn’t know!”
It was Crow’s younger brother Steve who convinced her to put “All I Wanna Do” on the record, reasoning that it was his and his friends’ favourite. Crow’s reticence stemmed in part from the fact that she didn’t write the lyrics, which are taken almost verbatim from a 1987 poem called “Fun”. “It was a strange coming-together of a song,” she remembers. “We jammed up this track and I had a book of poetry in front of me by this guy Wyn Cooper. I started reading it and created the chorus and then thought: ‘Well, I’ll go back and I’ll rewrite the words,’ which I did like five times and nothing ever felt the same. I thought: ‘I’ve had to work too hard on this thing, it can’t be that good!’ Then lo and behold… You just never know what’s gonna resonate with people, and that was definitely the anthem of the moment. What a gift!”
“All I Wanna Do” changed everything for Crow. A massive international hit, it propelled Tuesday Night Music Club to sell 8 million copies worldwide, won her a trio of Grammy awards in 1995, and made her one of the most recognisable artists in rock. Still, even this monumental success was soon soured by the men involved. Acrimonious disputes about who had written what devolved into sexist rumours that Crow was merely the front for the men’s talents, stories she now calls “beyond insulting”.
She decamped to Kingsway Studio in New Orleans with Bottrell to work on the follow-up record, but after a boozy 48 hours the producer disappeared, never to return (“I guess for personal reasons,” offers Crow). She called on an old songwriting buddy, Jeff Trott, and when they started writing together he suggested a chorus to her. It went: “If it makes you happy / Then why the hell are you so sad?”
“I loved it,” remembers Crow. “I’d just come off the heels of a very successful first record and had a lot of people who were betting against me, including the people that had contributed to the record. It was such a celebration of just taking the weight off of having to follow up that record. We just closed the door and said ‘F-you’ to everything and everybody. We were like kids in the basement: ‘We’re gonna do what we want to do and we may never put this out.’ It was really sheer joy making that record.”
Her 1996 album Sheryl Crow, eponymously named as a deliberate reintroduction, spawned the hits “If it Makes You Happy”, “Everyday is a Winding Road” and “A Change Would Do You Good”, proving beyond any doubt that Crow is very much her own talent. In Bottrell’s absence she produced the record herself, assisted by Kingsway engineer Trina Shoemaker. In 1998, Shoemaker became the first woman ever to win the Grammy for Best Engineered Album, for her work on Crow’s next record, The Globe Sessions. “I can unequivocally say that had Trina not been there, I wouldn’t have made the records that I made,” says Crow. “I mean, it really came in handy that the album did well because it certainly bolstered our argument that women can do as well in the studio as men can.”
The album also showcased the fearless political streak that runs through Crow’s music. It was banned from sale in Walmart stores across America because of a lyric on the song “Love is a Good Thing”, which she refused to change: “Watch our children as they kill each other / With a gun they bought at the Walmart discount stores”. Another track, the scathing protest song “Redemption Day”, was written after Crow played a USO (United Service Organisations) show to American peacekeepers in war-torn Bosnia and was struck that there had been no equivalent intervention by the US in the Rwandan genocide. “At the time it was pretty graphic to see dead bodies in Rwanda on TV and to know that no one was stepping in to defend these people,” she says. “That was the impetus for writing the song.”
It took on a life of its own. Years later, in early 2003, Crow received a call from Johnny Cash to ask if he could record his own version of “Redemption Day”. He quizzed her at length about why she’d written each line before recording his version, shortly before his death. For Crow, having Cash want to record her song and invest himself in it so deeply was the highest accolade she could imagine.
But the song wasn’t done with her yet. In 2019, Crow came to the decision that she no longer wanted to make albums, figuring that listeners to streaming sites cherry-pick tracks anyway, and preferring the immediacy of putting out punchy singles like last year’s anti-Trump broadside, “In the End”. To mark her final record, Threads, she rounded up friends and heroes to collaborate with, including Stevie Nicks, Keith Richards, and even ex-boyfriend Eric Clapton. The album’s centrepiece, however, is her hair-raising reworking of “Redemption Day” as a duet between herself and the late Cash’s inimitable vocals. “I think that to be able to sing that song posthumously with Johnny Cash has been the biggest gift of my entire career,” she says.
Crow, like Cash, is a child of the Mississippi Delta. She was born and raised in Kennett, Missouri, a city of just 10,000 people that lies – as she reflected in the title of her 2010 rhythm and blues album – 100 Miles from Memphis. She grew up surrounded by music. Her parents, Wendell and Bernice, were in a swing band together and would often play late into the night while Crow and her siblings slept on the stairs so they could eavesdrop on the party. Their house contained no fewer than six pianos.
“My mom was a piano teacher and she was very forward-thinking,” explains Crow. “She had group lessons where she’d have four kids at a time in the music room, and then there’d be the piano in the living room that we practised on. It would all be going on all the time. I attribute some of my ability to hear myself in the world to just being able to pick myself out of all that random chaos.”
Chaotic it may have been, but that maelstrom of sound and passion forged in Crow a belief in the power of music strong enough to withstand the realities of how cruel, corrupt and abusive she learned the business could be. It’s why she’s so excited this week to be going down to the little church she built for herself as a place of inspiration and meditation, to play her songs for as many people as want to hear them.
“Whether 10 people see it or 10,000 people see it, for me it’s essential that I connect to something bigger, to remind myself of what music is and what art is, and why I’ve built my whole life around it,” she says. “There’s something baptismal about it for me, to connect to something that is not definable but that definitely changes the molecules for all of us.”
Crow moves her hand over her heart as she sets out the tenets of her faith. “Music and art: it’s what will get us through all of these really strange times,” she says with conviction. “Something that penetrates and resonates in that same spot in all of us.”
Sheryl Crow: The Songs and the Stories global live-stream takes place on 18 June. For viewing times and tickets visit http://driift.link/SherylCrow. Crow’s new live album ‘Live From The Ryman And More’ is released 13 August
Join our new commenting forum
Join thought-provoking conversations, follow other Independent readers and see their replies