Her songs may evoke a sunny, laid-back LA vibe, but singer-songwriter Sheryl Crow, 60, has had her share of turbulence in her three-decade, nine-Grammy-award-winning career. In a new Showtime documentary, “Sheryl,” she chronicles the highs and lows of becoming one of the world’s top-selling female musicians.
And although Crow never spectacularly crashed to rock bottom like some rockers have, she illuminates how tenuous mental health can become in the harsh light of fame, and what it was like to be an ambitious woman in music in the decades before the MeToo movement.
Below, some of the most compelling aspects of the documentary, directed by Amy Scott (“Hal”), out May 6.
Before she was famous, she was a Missouri music teacher
Crow, a Missouri native, took a job teaching grade school music after she graduated from the University of Missouri, and sang in cover bands at night. Through a musician friend, she eventually got a gig singing in a McDonald’s commercial, which she says paid more than her first two years of teaching — and convinced her to move out to LA to chase her dreams.
She was once linked with Michael Jackson in the press
One of Crow’s first music industry jobs was as a backup performer on Michael Jackson’s “Bad” tour in the late 1980s, during which she would duet with Jackson on the song “I Just Can’t Stop Loving You.” She became somewhat friendly with Jackson, and he invited her to his hotel room to watch old movies. Jackson would have Bubbles the chimp with him, she says: “It was crazy.” Photos of the two onstage were used in the press with headlines suggesting they were an item — which they never were. “I was pretty naive, but I still thought it was so weird that Michael had a couple little boys with him on the road at different times,” she says. “Now knowing what is alleged, it makes me sad for the life he had. Obviously, it makes us all sad for the children. It’s just devastating to even think about.”
Jackson’s manager allegedly sexually harassed her
Frank DiLeo, Jackson’s manager, took a liking to Crow and her singing voice and wanted to work with her, she says. But his help came with conditions; he would allegedly frequently make unwanted advances, a pattern she documented not-so-subtly in her song “What Can I Do For You”: “I have so much to offer/If you just be nice/If you do what I say/ And don’t make me say it twice.” It ended up on her 1993 debut album, “Tuesday Night Music Club.”
When she tried to get legal help, she was turned away
Crow says she reached out to a high-powered attorney in LA with her concerns about DiLeo, telling him that the manager had threatened she would never work in the industry again if she spoke out against him. “I’d been told I needed to watch my back,” she says she told the attorney. “And at the end of our meeting, he said, ‘Look, you’ll come out ahead if you just stick it out. There are people that would die to be in this situation.’ Crow says the dismissal sent her into a tailspin. “I just sunk into the darkest, most depressed place. Just disappointment at the way the real world worked.”
She appeared on the short-lived musical series ‘Cop Rock’
Before it folded after only 11 episodes, Crow snagged a role in the finale of this ill-conceived 1990 musical police procedural; “Sheryl” shows a clip of a big-haired, cardigan-wearing Crow singing and dancing down a hallway.
She was accused of driving an author to suicide
When her first album took off, Crow was invited to appear on “Late Show With David Letterman” in 1994. It was her first talk-show appearance, and Letterman invited her to sit and chat after she performed. He asked her if her song “Leaving Las Vegas” was autobiographical and, she says, she became flustered and told him it was. In reality, she’d co-written the song with collaborators and got the title from the novel “Leaving Las Vegas,” by John O’Brien. A few weeks later, the troubled O’Brien killed himself, and his death was linked to Crow’s misstatement. It’s the one time in the documentary she’s overcome with emotion and breaks down.
She stood up to a Walmart ban of her album
In the song “Love Is a Good Thing” on her eponymous 1996 sophomore album, Crow’s lyrics included: “Watch out sister, watch out brother/Watch our children while they kill each other/With a gun they bought at Walmart discount stores.” She says in “Sheryl” that she was told by Walmart to change the lyrics or leave off the song, or they’d refuse to sell it. She kept it on, saying that their insistence made her feel more strongly about making an anti-gun statement — even if it made it harder for people in places like Kennett, her Missouri hometown, to buy the album.
Lance Armstrong proposed to her after he was busted for doping
Crow dated pro cyclist Lance Armstrong for three years, starting in 2003. When doping began to swirl around Armstrong, Crow says they had a major blow-up — which he followed by dramatically proposing to her with a huge diamond ring. “It was what I wanted,” she admits in the documentary, “but not like that.” The two later broke up.
She turned to Bob Dylan for help with writer’s block
When she was going through a period when she couldn’t seem to get any songs finished, Crow turned to Bob Dylan, who had become a friend, thinking that the veteran musician must have gone through some similar bouts. She called him and told him she had spent eight months unsuccessfully trying to finish an album. “That’s not good,” he told her, she relays in the doc. Had he had experience with this, she asked? His answer, to her chagrin: “No, never!”