Film Review: ‘Sheryl’: Sheryl Crow Documentary Shows Us Why We Shouldn’t Believe Everything We Read

Mark Jackson
Most people became aware of Sheryl Crow via her 1993 debut album, “Tuesday Night Music Club” with the hit song “All I Wanna Do.” I really became aware of her while watching “Woodstock 1994” on VHS about a year after thinking I should have fled Manhattan and attended the concert.
She was wearing bright yellow pants and singing a slow song, and I remember finding the song boring but her stage presence electrifying. Her huge charisma is closely tied to her signature voice quality, which I’ve always defined as a blend of the fascinating nonchalance of that kind of prettiest, coolest, beat-of-her-own-drum artsy girl in high school, who nevertheless cheerled and baton-twirled (which Sheryl did), combined with an ability to do a James Brown scream, except with an alluring, muted, girly-girl coyness—with vicious musical chops. And guitar-hero moves. Sheryl Crow onstage at Woodstock ‘94 was the personification of a rock star, although she wasn’t one yet.


Sheryl Suzanne Crow, born on Feb. 11, 1962, in Kennett, Missouri, was, like country music star Shania Twain, immersed in music from a young age. She became an elementary school music teacher in the St. Louis suburb of Fenton, then moved on to do commercial jingle work for McDonald’s, and eventually caught a big break and went on tour (with giant, ‘80s hair almost as big as herself) as Michael Jackson’s backup singer for his global “Bad” tour to Tokyo in 1987.

In 1992, she attempted a solo album, which tanked. She started hanging out with a group of Los Angeles musicians who called themselves the “Tuesday Night Music Club.” One Tuesday, she went to the library, took out a book of poetry, had her musician group play some music while she recited the poem over it, and thus  “All I Wanna Do” was born—a perfect example of mediocre artists borrowing, and great artists stealing. She did call the original author, John O’Brien, and ask permission later.

Sheryl Crow on acoustic guitar in her studio in "Sheryl." (Showtime)
Sheryl Crow on acoustic guitar in her studio in "Sheryl." (Showtime)

However, in her first-time-ever TV interview, David Letterman asked her if the song was autobiographical, and, being young, star-struck and nervous, she giggled “Yeah!” This inadvertent moment of not giving credit where credit was due led to a rumor that this was the main reason John O’Brien committed suicide, which was later refuted by the poet’s sister, but not before causing some damage to Crow’s reputation.

This tragedy, along with a few other controversial incidents, such as the death of her boyfriend Kevin Gilbert, and her publicly battling breast cancer (to get attention? Really?) led to a reputation of her having a tendency to use people. To hear Sheryl Crow herself tell it (and shed tears) is to realize that we shouldn’t believe everything we read in the news.

Speaking of using, it’s interesting to hear the origins of her early hit “What I Can Do For You,” about her manager at the time, Frank DeLio (who was also a mobster), who promised her the world in highly creepy ways.

Crow quickly emerged as a polished, jack-of-all-trades (and master of all of them) singer to become a bona fide rock star.

Middle Period

Crow’s reputation that she used people to get where she got is refuted by the long trail of incredibly hard work that demonstrates, over time, her level of talent as a musician, performer, and producer. And once she hit her stride, it was nonstop composing, producing, hit-making, collaborating, touring, and winning awards.
Sheryl Crow on bass, in "Sheryl." Crow plays acoustic, electric, pedal steel, and bass guitars, piano, accordion, and harmonica. (Showtime)
Sheryl Crow on bass, in "Sheryl." Crow plays acoustic, electric, pedal steel, and bass guitars, piano, accordion, and harmonica. (Showtime)

Interview subjects willingly testify to the facts, and Sheryl Crow has lots of friends to back her up. There’s actress Laura Dern (they roomed together briefly), Tuesday Night Music Club member Bill Bottrell, longtime manager/collaborator and friend Scooter Weintraub (who looks like actor Sam Elliott’s younger brother), fellow country musician Emmylou Harris, singer-songwriter and producer Brandi Carlile, fellow rock star Keith Richards of the Rolling Stones (who affectionately calls her “little sister” and bemusedly tells of her ability to easily handle the overbearing Mick Jagger onstage), her parents Wendell and Bernice Crow, and many more.

The failed romantic engagements are quickly touched on. Really, bicyclist Lance Armstrong, who bought her a massive diamond engagement ring in the wake of his lying about doping in his relentless bid for greatness in his sport, deserves short shrift. Interestingly, in that little segment, the lyrics “lie to me,” from her song “Are You Strong Enough to Be My Man,” play in the background.

Sheryl Crow (L) and director Amy Scott at the South by Southwest Film festival. (Showtime)
Sheryl Crow (L) and director Amy Scott at the South by Southwest Film festival. (Showtime)

The End

There are plenty of behind-the-scenes, never-before-seen archival footage of Crow in the studio and on the road, from 20 years’ worth of touring.

Sheryl Crow comes off as distinctly Midwestern in her warmth, matter-of-factness, generosity, coolheadedness, and friendliness. With the adoption of two boys, Sheryl managed to have it all, in the modern sense. I’ve gathered from reading about her career over the years that she suffered from the depression and loneliness of life on the road, but a musical talent this big cannot be denied. It just takes massive will power to make it work. And that’s what aspiring musicians and artists everywhere stand to take away from this documentary: that one should make sure one has that level of ability to work like a dog, even when sick and exhausted, before embarking on such a potentially treacherous career path.

Shania Twain demonstrates the same thing in the recent documentary about her that just came out. Musicians, music fans, and casual listeners should watch both. “Sheryl” is far more rewarding, but both demonstrate that in order to succeed in the American music business, same as in show business, you generally need world-class talent, looks, and an insatiable ability to work hard.

“Sheyl” is currently streaming on Showtime.
Promotional poster for "Sheryl." (Showtime)
Promotional poster for "Sheryl." (Showtime)
‘Sheryl’ Documentary Director: Amy Scott Running Time: 1 hour, 34 minutes Release Date: May 6, 2022 Rating: 3 stars out of 5
Mark Jackson is the chief film critic for The Epoch Times. In addition to the world’s number-one storytelling vehicle—film, he enjoys martial arts, weightlifting, Harley-Davidsons, vision questing, rock-climbing, qigong, oil painting, and human rights activism. Mark earned a bachelor's degree in philosophy from Williams College, followed by a classical theater training, and has 20 years’ experience as a New York professional actor, working in theater, commercials, and television daytime dramas. He recently narrated the Epoch Times audiobook “How the Specter of Communism is Ruling Our World,” which is available on iTunes and Audible. Mr. Jackson is a Rotten Tomatoes-approved film critic.
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