Sheryl Crow gets candid about sexual harassment, depression and fighting cancer in new documentary

Sheryl Crow wasn’t initially keen to document her life.

“I’ve always felt like documentaries were told after someone has already gone or after a fiery plane crash,” she said at a recent Television Critics Association panel.

But her manager of 30 years, Scooter Weintraub, convinced Crow that her decades as a woman in the music business meant she had a potent story to tell.  

So the perennial hitmaker accepted the assignment of “remembering, reflecting and revisiting” her life.

The result is “Sheryl,” a 90-minute documentary debuting Friday on Showtime (9 p.m. EDT/PDT).

Directed by Amy Scott (“Hal”), the film encompasses Crow’s noteworthy career, touching on the songwriting credit scandals with her Tuesday Night Music Club (her band on breakthrough 1994 smash “All I Wanna Do” and also the name of her multiplatinum debut album), the making of her three subsequent mega-selling albums (“Sheryl Crow,” “The Globe Sessions” and “C’mon C’mon”), her struggles with depression and her breast cancer fight.

The documentary also includes interviews with a varied cast from Crow's orbit: Keith Richards, Jason Isbell and longtime friend and former roommate Laura Dern.  

Sheryl Crow says at this point in her career, it's all about "gratitude."

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Crow, at 60, is a legacy artist in the most complimentary sense. But it’s a term she says she struggled with because “I thought, oh, that just means you’re old and you’ve been around long enough to be put in the category of legacy.”

But “for me, it’s all about gratitude,” she says. “I play (these songs) with total gratitude because I know it’s not an everyday thing to become the soundtrack to people’s lives.”

Here are some key revelations from the documentary: 

Why Crow was 'terrified' during Michael Jackson tour

Most fans already know that Crow’s early career break arrived with a role in Michael Jackson’s 1987 Bad tour. Footage of her massive helmet of hair and teeny skirt as she sang “I Just Can’t Stop Loving You” with Jackson onstage is juxtaposed with Crow talking now about offstage activities, such as watching “Amos ’n’ Andy” in a hotel room with Jackson and his chimp, Bubbles.

“I was naive," Crow says, "but I still thought it was weird that there were a couple of little boys on the tour with him. It makes me sad for the life he had and obviously sad for the children.”

Crow’s two-year stint with Jackson dovetails with the sexual harassment she alleges she experienced from his late manager, Frank DiLeo, which she also documented in 2020's audiobook memoir, "Words + Music." “It was a constant battle to keep him off of me," she says. She finally contacted an attorney (“I was terrified,” she recalls) who told her to soldier through because “there are people who would die to be in this situation.”

Her Lilith Fair days were an inspiration for Brandi Carlile

While Sarah McLachlan spearheaded Lilith Fair, the all-female touring ensemble that launched in 1997 with artists including Jewel, Tracy Chapman, the Indigo Girls, Fiona Apple and Emmylou Harris, Crow was a fervent supporter and participant.

The tour was inspirational for at least one fledgling musician, Brandi Carlile, who shares onstage at one of her own concerts that she saw Lilith Fair in the same venue as a teenager. The female-centric concept showed her that, “I can get out there with a guitar and be the boss.”

Sheryl Crow says music is her "lifeline" as she releases the Showtime documentary "Sheryl."

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Crow wrote 'C'mon C'mon' in the throes of deep depression

Crow is open about her struggles with depression. In an affecting segment, she candidly talks about how she was so emotionally crippled writing her “C’mon C’mon” album that she doesn’t remember penning its final track, “Weather Channel,” a song that sighs with sadness. 

As Crow plays it on her acoustic guitar in the documentary, the effects of its lyrics about the onset of suffocating emotions still visibly rattle her core. “I got lab coats/who will bring me a panacea/while I’m watching the weather channel/and waiting for the storm,” she sings with eyes closed. The “black dog that scratches my door” in the lyrics is, Crow thinks, a reference to how Winston Churchill described his descent into darkness.

 “Just a little happy song about suicidal tendencies,” she says with a wry smile and teary eyes. 

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Sheryl Crow's "Sheryl" documentary follows her upbringing by musician parents and becoming a teacher in Missouri to going on the road with Michael Jackson and her enduring solo success.

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In the early 2000s, Crow engaged in a high-profile relationship with cyclist Lance Armstrong. “The first year, it was fantastic,” she says. “I was ready to get married.” 

Their engagement fizzled in 2006, but Crow remains philosophical about their time together. “It does get complicated when you have to dim your light to be in somebody else’s light,” she says as her song “Strong Enough” plays in the background. The line “lie to me” is timed to footage of Armstrong denying doping allegations made against him. (In 2013, Armstrong admitted to using performance-enhancing drugs throughout his career.)

Shortly after their breakup, Crow went for a routine mammogram, leading to her breast cancer diagnosis. “The craving to see pictures of me at my worst, I was (mad). I felt like I didn’t deserve it,” she says of being followed by the paparazzi while undergoing treatment.

Joe Walsh appears to talk about how Crow helped his wife, Marjorie Bach, after she, too, was diagnosed with breast cancer. “She taught my wife (that) you have to get educated, you have to learn about it, and then you can deal with it. … Sheryl is a survivor,” Walsh says.

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