Sheryl Crow looks back on her winding road to stardom in new documentary

Grousing about who's been overlooked by the Rock and Roll Hall of Fame is almost as engaging as seeing who gets in. If Sheryl Crow wasn't already on your wish list, she will be after you watch a new documentary on her winding road to fame.

In "Sheryl," debuting this weekend on Showtime and available on the channel's app, the nine-time Grammy winner celebrates a career that's still going strong. Her latest tour stops July 5 at the Ledge Amphitheater in Waite Park, Minn.

"I've always felt like documentaries were told after someone has already gone on after a fiery plane crash," Crow, 60, told TV critics during a virtual news conference in February. "It was my manager who has been with me from the very, very beginning who said, 'You've got a powerful story. It's time for you to tell it.'"

That tale might have been more fascinating if the film was longer than 90 minutes.

Crow mentions being sexual harassed by a manager, but offers scant details. Some of her best material, including "Good Is Good," "Steve McQueen" and her cover of Cat Stevens' "The First Cut Is the Deepest" gets largely overlooked.

Her relationship with disgraced cyclist Lance Armstrong gets about as much screen time as a montage of her goofing around with her two adopted kids. There's no mention of her romance with Eric Clapton. (Was her hit "Favorite Mistake" about him? We may never know.)

But director Amy Scott does dedicate ample time to a few of the more painful moments in her subject's career, including her 1994 appearance on "The Late Show With David Letterman" in which she appeared to take full credit for writing "Leaving Las Vegas." The interview upset her collaborators. Novelist John O'Brien, who contributed the song's title, committed suicide three weeks later.

"I knew the Letterman sequence was going to be challenging. How are we going to handle this in a way that is honest?" asked Scott, who joined Crow in the virtual conference. "But when we got there, it felt honest because she was so vulnerable. If she hadn't been, that would have changed the story and that would have changed my perspective on who she was."

Crow is also frank about other topics, including depression and being diagnosed with breast cancer. But she saves her strongest comments for the subject of being a small-town Missouri gal struggling to stay afloat in a sexist business.

"It was difficult. I was sitting there for hours on end, and remembering and reflecting and revisiting was extremely emotional," she said about the interview process. "I'm a woman. I've seen a lot of things change. I've also seen a lot of things not change very much at all. So, yeah, it was emotional. It was exhausting, and ultimately, it was really gratifying."

The film has its lighter moments, like when she recalls watching "Amos 'n' Andy" reruns with Michael Jackson when she was a backup singer on his tour and Keith Richards musing on how she held her own with Mick Jagger on stage. There's also footage of Crow jamming with Prince on "Everyday Is a Winding Road." At one point, Crow does an impersonation of her friend Bob Dylan.