along the winding road with a country-rockin’ queen

When Sheryl Crow rocked Glastonbury in 2019, she reminded us how many great songs she released during her ’90s purple patch: ‘All I Wanna Do’, ‘If It Makes You Happy’, ‘Everyday Is A Winding Road’, ‘My Favorite Mistake’. This career-spanning documentary offers an insight into how she wrote (and produced) her biggest hits, but it’s most compelling when it focuses on Crow herself. Because she’s such a seasoned pro on stage, it’s easy to forget how many obstacles she overcame to become, as she acknowledges rather ambivalently here, a quote-unquote “legacy artist”.

Directed by Amy Scott, who previously made a detailed doc about Hollywood director Hal Ashby, Sheryl is brisk but pretty comprehensive. It barrels through her music-infused upbringing in small-town Missouri, where her mum gave piano lessons and Crow became obsessed with James Taylor and Stevie Nicks, and into a brief engagement to a “born again Christian” and sort-of-big break singing in a McDonald’s advert. Crow was working as a schoolteacher at the time, but when the burger commercial paid her the equivalent of two years’ salary, she quit and upped sticks to Los Angeles. It’s far from the last time this film highlights her remarkable tenacity.

In California, Crow auditions for Michael Jackson‘s ‘Bad’ tour, lands a job as his backing singer, then gets to duet with him on ‘I Just Can’t Stop Loving You’ night after night. Crow recalls a bizarre evening watching movies with Jackson and his pet chimp Bubbles, but also concedes she was “naive” not to think harder about why two young boys formed part of his entourage. Heartbreakingly, she says the tour led to her being persistently sexually harassed by Jackson’s then-manager, Frank DiLeo, a grim, gangster-like figure. When an industry lawyer advises Crow to stick it out for the sake of her career, Crow recalls being thrust into the “darkest, most depressed place”.

Though devastating, this experience doesn’t affect her drive. While working as a waitress in the Valley, she slips a producer a demo tape with his bill, then finds herself welcomed into a loose collective of musicians known as the Tuesday Night Music Club. Their boozey jam sessions bloom into Crow’s iconic 1994 debut album, home to the huge hits ‘All I Wanna Do’ and ‘Strong Enough’. Crow’s career explodes, but she isn’t fully prepared for the glare of the spotlight. During her first big TV interview on David Letterman’s talk show, a nervous Crow bungles an answer about whether her song ‘Leaving Las Vegas’ is autobiographical. She says “yeah” but doesn’t acknowledge her five co-writers or the fact its title is borrowed from John O’Brien’s novel of the same name. Her collaborators feel aggrieved and shortly afterwards, O’Brien commits suicide. This tragedy has nothing to do with Crow, but the experience is clearly so traumatising that it still brings her to tears nearly 30 years later.

At times, it feels as though there’s more to be said: the doc doesn’t gloss over Crow’s engagement to disgraced cyclist Lance Armstrong, but neither does it explore the presumably challenging experience of living with a world-famous athlete at the centre of a doping scandal. Then again, this is Crow’s story, not his. Scott concentrates instead on other seismic events in Crow’s personal life including her battle with breast cancer, decision to become a mother by adoption, and brutal bouts of depression, Crow gives a beautifully intimate performance of ‘Weather Channel’, a subdued ballad from 2002’s otherwise sunny ‘C’mon C’mon’ album, then describes it wryly as “a happy song about suicidal tendencies”. It’s a real highlight of the film.

Like so many docs of this ilk, Sheryl features contributions from the artist’s famous mates. Unlike so many of them, these talking heads do add value. An impressed Keith Richards says that when Crow joined The Rolling Stones on stage in Miami in 1994, she was “very well able to handle Mick Jagger“. Brandi Carlile illuminates why Crow, who’s “straight as an arrow” in her own sexuality, has a loyal following among queer women. And Laura Dern recalls life as Crow’s unlikely housemate in the ’90s. If Dern’s recollections are a little spacey in that Hollywood kind of way, it just highlights how grounded Crow herself seems in comparison.

Back in 2019, Crow promoted ‘Threads’ as her final album, but she doesn’t say as much here. Maybe she’s at least reconsidering? Either way, she’s characteristically astute when it comes to analysing her current status as a “legacy artist”. It means “you’ve stood the test of time”, Crow notes, but also that “you’re old and just haven’t gone away”. After watching Sheryl, you’ll be really glad she hasn’t.