Stream It Or Skip It: ‘Sheryl’ on Showtime, A Doc Looking Back On Sheryl Crow’s Career Highs And Life Lows

Sheryl (Showtime), the new documentary about musician and songwriter Sheryl Crow’s music, life, and career, rambles on the rhythms of her hit songs, enduring radio favorites like “If It Makes You Happy” and “All I Wanna Do,” the beer buzzy riff that originally put her on the map all the way back in 1994. Crow speaks candidly here about her journey, alongside testimonials from friends like Laura Dern, Brandi Carlile, and Joe Walsh.

SHERYL: STREAM IT OR SKIP IT?

The Gist: “I think the negative connotations associated with ‘driven’ and ‘perfectionist’ usually get put in that category of ‘bitch,'” Sheryl Crow says in an interview clip early on in Sheryl, and that grit and sentiment guides director Amy Scott’s documentary from the singer, musician, and songwriter’s early days, transitioning from life as a schoolteacher and cover band singer in her native Missouri to scrabbling for music business traction in late 1980’s Los Angeles, through guest shots on the ill-fated Steven Bochco “musical procedural” Cop Rock, to singing in Michael Jackson’s backup band on the 1987 Bad tour and finding sudden and lasting success with her debut full-length, 1993’s Leaving Las Vegas. With the assistance and support of Scooter Weintraub, her longtime manager, Crow seized on the saturation of singles like the title track and “All I Wanna Do.” She netted Grammys for Best New Artist and Record of the Year, shared a stage with the Rolling Stones, and decamped to Daniel Lanois’ New Orleans studio to write a follow-up record. None of this was without controversy, of course. In her interviews for the doc, Crow breaks down when she revisits the contention surrounding songwriting credits for Las Vegas and in particular “All I Wanna Do.”

Postcard-like chapter headings in Sheryl trace Crow’s journey as a recording artist, from the French Quarter and the sessions for Sheryl Crow, which she also produced, to setting out in 1997 on the groundbreaking Lilith Fair tour alongside her fellow female artists in Sarah McLachlan, Tracy Chapman, and Paula Cole. By 1998 she was in complete control, building her own studio in New York City to record The Globe Sessions, a record for which she garnered another Grammy, and she hit the road for more touring. Still, it was a grind. “Fame is not natural,” Crow says. “And it’s also a very energetic experience. People are projecting their energy at you.” So what happens when you hit a wall, and can’t please the fans, the label, or yourself? You call Bob Dylan for advice, of course. Crow goes into a pretty solid Dylan impersonation as she recalls their conversation.

Writer’s block is one thing. But chronic depression is quite another, and despite the balmy, youthful vibes of her 2002 hit “Soak Up the Sun,” Crow was suffocating. Sheryl details the singer’s confrontation with and management of her depression, as well as the dissolution of her relationship with Lance Armstrong, her breast cancer diagnosis, and her road to recovery, where she drew on the support of her mother and father and friends like Laura Dern. And by the end notes of Sheryl, Crow has settled into the legacy years of her career. She’s raising her two adopted boys on the farm property she purchased in Nashville, complete with a home studio fitted out with her ongoing collection of vintage gear.

What Movies Will It Remind You Of? She’s not among the peers and pals of Crow who are interviewed. But Alanis Morissette is mentioned in Sheryl, alongside other women artists who had broken out and established their popular voice in the Lilith Fair era, and that legacy is explored in Jagged, the 2021 doc about Morissette that appeared as part of HBO’s Music Box series. HBO also featured Tina in 2021, a riveting, revealing doc about Tina Turner’s storied personal and professional journey.

Performance Worth Watching: When sitting for a documentary about your life and career, it’s handy to have an old pal like Keith Richards in your back pocket. Each segment with the legendary Rolling Stone rings with his wit and ageless verve, from his early appreciation of Crow’s talent and toughness – complete with a good-natured jab at Mick Jagger – to his take on doing music until you die. “There’s no hidden potion,” Richards says. “You just get stuck here. You’re still doing it, and you still love it.”

Memorable Dialogue: “There’s a weird thing that happens when you become a ‘legacy artist,'” Crow says, sitting at home on her farm in Nashville, in the writing room/recording studio she built above the stable where her horses reside. “It’s sort of a sideways compliment. It’s like, ‘You have stood the test of time, but also, you’re old and you just haven’t gone away.”

Sex and Skin: None.

Our Take: When asked about that connotation that she’s “driven” – which some might say is a euphemism for “bitch” – Sheryl Crow doesn’t necessarily disagree. But she doesn’t submit to that, either, or back down even an inch. Determination, certainty of plan: these have always been her calling cards, and especially so in an industry that traditionally hasn’t valued women. As Brandi Carlile says in Sheryl, women in the music industry have to work twice as hard. And as Bill Bottrell, Crow’s “Leaving Las Vegas” collaborator says, Sheryl’s work ethic is second to none. So if her approach has at times turned people off, or rubbed them the wrong way, so be it. Sheryl Crow isn’t apologizing. She’s rightly proud of the effort she’s invested in her career, all of the songwriting, singing, playing of multiple instruments, and producing her own music (“If she was a man, people would talk about her like Prince,” Jason Isbell says in Sheryl), and looking at it from her tier as nine-time Grammy winner and seller of 50 million albums, she can say she wouldn’t have done it any other way, even if her string of failed relationships speaks to some personal trauma. At one point in Sheryl, she just shrugs. “I’m just not around very much.” She’s a musician, a road dog, and a gear freak. And she’ll probably always be most comfortable when she’s behind a guitar, leading her band. There’s a clip in Sheryl of Crow chilling with Willie Nelson, backstage at a concert somewhere. They both agree that gigging and the road have removed certain aspects of their personal lives. But neither Sheryl nor the Red Headed Stranger apologizes for that.

Will you stream or skip the music documentary #SherylDoc on @Showtime? #SIOSI #SherylCrow

— Decider (@decider) May 7, 2022

Our Call: STREAM IT. The format of Sheryl is pretty standard-issue – she scrapped, she succeeded, she dug in, she excelled, she crashed and burned; she emerged relatively unscathed –  but within that frame is the vitality and strident personality of an artist who has consistently, unapologetically done things her own damn way.

Johnny Loftus is an independent writer and editor living at large in Chicagoland. His work has appeared in The Village Voice, All Music Guide, Pitchfork Media, and Nicki Swift. Follow him on Twitter: @glennganges