‘Sheryl’: Film Review | SXSW 2022

Sheryl Crow opens up about her tumultuous life and career in this Showtime documentary directed by Amy Scott.

Sheryl Crow is a master of her craft. The 60-year-old musician has released more than 10 albums and won nine Grammy Awards. She has sold millions of copies of her records and influenced a generation of musicians, whether they know it or not. Crow, who got her start on Michael Jackson’s 1987 Bad world tour, has had the kind of career some artists can only dream of. She has been changed by it, but in Sheryl, a documentary about Crow’s life, it’s clear that she isn’t jaded.

Directed by Amy Scott, the film finds Crow speaking with the enthusiasm and reverence of an apprentice. She is in awe of her life’s peaks and valleys. She can laugh at herself and her early naïveté. She doesn’t take for granted how music makes her feel and what it does for her. And, above all else, she respects the tools — the vintage guitars and amps, for example — and the people, that make it all possible.


The Bottom Line

Sweet but distant.

Venue: SXSW Film Festival (24 Beats Per Second)
Director: Amy Scott

1 hour 34 minutes

Sheryl captures these facets of its subject’s gratitude with ease. But when it comes to more rigorous analysis — a bit of pushback, a touch of tension or cultural context — the documentary leaves something to be desired.

To be fair, Sheryl, which will premiere on Showtime on May 6, isn’t billed as a revealing exposé or a platform for talking heads. It is a deserved appreciation of an artist whose music has transformed the lives of many people — including her own. Scott, who last directed the Sundance flick Hal, aims for intimacy, candor and humor. Her respect for Crow guides the documentary, which dutifully chronicles the musician’s journey to stardom and the bumps she faced along the way. But that adoration eventually limits the work’s scope, forcing it to recapitulate a handful of themes to get us to the credits.

Crow’s insatiable curiosity and desire to improve are up for study first. The musician was born in Missouri and, she recalls through one-on-one interviews, remembers the magnetic hold music had on her. Her mother was a piano teacher, and her parents were members of a swing band. She remembers sneaking downstairs with her sisters to watch their rehearsals. Crow would go on to study music composition at the University of Missouri in Columbia. After graduating, she taught music to children with special needs. Two years into that job, she left Missouri for Los Angeles in pursuit of a dream she couldn’t shake.

Los Angeles, like New York for another kind of artist, sobered Crow. She spent her early days mailing random music executives her demos and waitressing. Her big break came when she smooth talked her way into auditioning for Michael Jackson’s Bad tour. She was impressive. For the next year she worked closely with the King of Pop and showed off her talents in front of larger audiences.

Sheryl paints a lovely portrait of those early years, using interviews with Crow, old photos and camcorder footage. Crow met her best friend —  and later manager — Scooter Weintraub during this time; he speaks fondly and protectively of her and their friendship. But the doc stumbles when it addresses Jackson and the allegations against him, which Crow mentions briefly. To some degree, the acknowledgement is required, but the way it’s inserted — fleetingly, but very deliberately — feels unnatural.

It also betrays Sheryl’s main problem (and that of many recent music documentaries): the tension between honoring Crow’s privacy and wrestling with the more delicate details of her life. The doc approaches moments of surprising intimacy only to shy away from their implications. It treads lightly over the most painful memories of Crow’s journey, but doesn’t find a way to make up for the resulting thinness of those segments of the doc.

After working for Jackson, Crow starts dating musician Kevin Gilbert. She joins him and some other guys for informal songwriting sessions as a group called Tuesday Night Music Club (later the title of her debut album). Fans of Crow know what happens from here. The album — especially the single “All I Wanna Do” — catapulted her to fame. Sheryl provides a fine summary of those years, giving its subject time to correct the record about the songwriting credit. Reflecting on the painful interview with David Letterman, in which Crow, without thinking, inaccurately said the song “Leaving Las Vegas” was autobiographical, moves her to tears.

Perfectionism hounded Crow after the success of Tuesday Night Music Club. Every album thereafter provided an opportunity for her to best herself — and she did. Not only could Crow sing and play instruments, but she wrote her songs and produced her records. Yet the doc, and some of Crow’s friends, suggest that she was never fully recognized for the breadth of her talent. Two themes converge: Crow’s personal drive to be perfect and the way the industry’s sexism hobbled her career. Here, one wishes that Sheryl unshackled itself from the biographical playbook and charted its own course a bit more. The #MeToo movement has made it easier to identify instances of sexual harassment (like the one Crow faced at the hands of an early manager) and to articulate the realities of sexism within industries; it would have been worth doing so in the context of Crow’s career.

Instead, Sheryl treats these anecdotes — as well as admissions of the demands of fame and the pressures of celebrity — somewhat vaguely before marching onward. Crow also talks briefly about her highest-profile relationships, including her engagement to Lance Armstrong, but she doesn’t dwell. Sheryl returns to its subject’s unrelenting drive and how it contributed to bouts of depression and burnout. These are followed by a breast cancer diagnosis, which leaves the artist shaken.

After (thankfully) recovering, Crow appraises her life. What had she accomplished? A ton! What did she want to do next? Motherhood was a priority, and Crow tenderly recounts how she came to adopt her two sons. Her testimony is followed by a beautiful montage of footage of Crow’s children spending days with her on tour, playing, laughing, being kids.

The arrival of Crow’s children shepherds the doc toward a warm end. Sheryl’s final act considers Crow’s legacy, and how her music has found a new generation of fans. In some ways, this project serves as a bridge between the past and the present, offering Crow’s old and new fans an opportunity to know her, up to a point.

Full credits

Venue: SXSW Film Festival (24 Beats Per Second)
Distributor: Showtime
Production company: Gunpowder & Sky
Cast: Sheryl Crow, Laura Dern, Keith Richards, Joe Walsh, Steve Jordan, Emmylou Harris, Brandi Carlile, Jason Isbell, Jimmy Iovine, Greg Phillinganes
Director: Amy Scott
Producers: Van Toffler, Scooter Weintraub, Brian Morrow, Jonathan Lynch
Executive producers: Vinnie Malhotra, Floris Bauer, Barry Barclay, David Gale
Director of photography: Jonathon Narducci
Composer: Heather McIntosh

1 hour 34 minutes