Sheryl Crow Talks Michael Jackson, Lance Armstrong in New Document

Her songs may evoke a sunny, laid-back LA vibe, but singer-songwriter Sheryl Crow, 60, has seen her share of turbulence in her three-decade, nine-Grammy-winning career. In a new Showtime documentary, Sheryl, she chronicles the ups and downs of becoming one of the world’s best-selling musicians.

And while Crow has never hit rock bottom as spectacularly as some rockers have, she sheds light on how fragile sanity can get in the glare of fame and what it was like to be an aspiring woman in the decades before the MeToo movement to be in music.

Here are some of the most compelling aspects of the documentary, directed by Amy Scott (“Hal”), out May 6th.

Sheryl Crow with a guitar in front of a microphone
Sheryl Crow in a still from a new Showtime documentary entitled Sheryl.
Courtesy of SHOWTIME

Before she became famous, she was a music teacher in Missouri

Crow, who is originally from Missouri, took a job teaching elementary school music after graduating from the University of Missouri and sang in cover bands at night. Eventually, through a musician friend, she landed a singing gig in a McDonald’s commercial that she felt was more profitable than her first two years as a teacher — and convinced her to move to LA to pursue her dreams.

She was once linked to Michael Jackson in the press

Sheryl Crow and Michael Jackson perform during the "BAD" Tour around 1988.
Sheryl Crow and Michael Jackson perform during the “BAD” tour circa 1988.

One of Crow’s first jobs in the music industry was as a backup performer on Michael Jackson’s “Bad” tour in the late 1980s, during which she performed a duet with Jackson on the song “I Just Can’t Stop Loving You.” She became friends with Jackson and he invited her to his hotel room to watch old movies. Jackson would have the chimp Bubbles with him, she says: “It was crazy.” Photos of the two on stage were used in the press with headlines suggesting it was an object – which it never was. “I was pretty naïve, but I still found it so strange that Michael had a bunch of little boys with him at different times,” she says. “Now knowing what is being claimed makes me sad for the life he had. Of course it makes us all sad for the children. It’s just devastating to think about.”

Jackson’s manager is said to have sexually harassed her

    In this October 27, 2009 file photo co-producer Frank Dileo arrives at the premiere of "Michael Jackson's This Is It,"  in Los Angeles.
Crow claimed that Michael Jackson’s manager, Frank DiLeo, seen above in 2009, made unwelcome advances.

Frank DiLeo, Jackson’s manager, liked Crow and her singing voice and wanted to work with her, she says. But his help came with conditions; He allegedly made frequent unintentional advances, a pattern she documented less subtly on 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 their 1993 debut album Tuesday Night Music Club.

When she tried to get legal counsel, she was turned away

Crow says she took her concerns about DiLeo to a senior LA attorney, telling him the manager threatened that if she spoke out against him, she would never work in the industry again. “I was told to watch my back,” she told the attorney. “And at the end of our meeting he said, ‘Look, you’re going to come out on top if you just persevere. There are people who would die to be in this situation.’ Crow says the layoff sent her into a tailspin. “I just sank into the darkest, most depressed place. Just disappointment with how the real world worked.”

She appeared in the short-lived musical series Cop Rock.

Before it came to fruition after just 11 episodes, Crow landed a role in the finale of this ill-conceived 1990 musical cop; “Sheryl” features a clip of a big-haired, cardigan-wearing crow singing and dancing down a hallway.

She was accused of driving an author to suicide

Sheryl Crow's first appearance on The Late Show with David Letterman in 1994
Sheryl Crow on The Late Show With David Letterman in 1994.

When her first album launched, Crow was invited to appear on 1994’s “Late Show With David Letterman.” It was her first appearance on a talk show, and Letterman invited her to sit down and chat after her performance. He asked her if her song “Leaving Las Vegas” was autobiographical, and she said she got nervous and told him it was. In fact, she co-wrote the song with collaborators, taking the title from John O’Brien’s novel Leaving Las Vegas. A few weeks later, a concerned O’Brien killed himself and his death was linked to Crow’s false testimony. It is the only time in the documentary that she is overcome with emotion and collapses.

She has fought against a Walmart ban on her album

Sheryl Crow
The singer opened up about her career in the new documentary Sheryl.
Courtesy of SHOWTIME

In the song “Love Is a Good Thing” on her 1996 second album of the same name, Crow’s lyrics included: “Look out sister, look out brother / Watch out our children while they kill each other / With a gun they.” bought at discount Walmart stores.” She says in Sheryl that she was told by Walmart to change the lyrics or omit the song or else they would refuse to sell it. She maintained it, saying her insistence has made her feel more empowered to make an anti-gun statement — even if the album is harder for people in places like Kennett, her Missouri hometown, to buy.

Lance Armstrong proposed to her after he was arrested for doping

Lance Armstrong and musician Sheryl Crow attend the Houston Rockets vs. Los Angeles Lakers playoff game at the Staples Center on April 28, 2004 in Los Angeles, California.
Lance Armstrong and Sheryl Crow at the Staples Center in April 2004.
Getty Images

Crow dated professional cyclist Lance Armstrong for three years beginning in 2003. As doping allegations swirled around Armstrong, Crow said they witnessed a big explosion – after which he dramatically proposed to her with a huge diamond ring. “It was what I wanted,” she admits in the documentary, “but not like this.” The two then broke up.

She turned to Bob Dylan for help with writer’s block

Sheryl Crow
The singer turned to Bob Dylan for help during a songwriting dry spell.
Courtesy of SHOWTIME

Going through a period when she couldn’t seem to finish songs, Crow reached out to Bob Dylan, who had become a friend, and figured the veteran musician must have been going through some similar struggles. She called him and told him that she had spent eight months trying unsuccessfully to complete an album. “It’s not good,” he told her, passing it on to the doctor. Did he have experience with it, she asked? His answer to her chagrin: “No, never!”

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