Had Sheryl Crow ended her music career with “If It Makes You Happy,” she still would’ve been one of the definitive voices of 1990s rock radio. Building from slack, brooding verses, the 1996 single strikes at the ache of unfulfillment as it leaps out of its bridge, with Crow soaring across her vowels. It was a perfect anthem for a certain kind of restless listener, someone grounded enough to appreciate the small things while still yearning for the bigger answers. But the singer-songwriter’s more cheerful hits—the bouncy glow of “All I Wanna Do,” the breezy reach of “Soak Up the Sun,” even the twangy road song she did for the Cars soundtrack—sometimes edged her harder-won achievements out of the spotlight: taking a strong commercial stand against Wal-Mart, surviving cancer, carving out a career between being too pop-friendly for grunge and too raw for the lighter pop market. Now, nearly 30 years into her career as a solo artist, she’s the latest semi-underdog star to have someone else set the record straight.
There’s a lot to cover. Within the slender 95-minute run time of a new Showtime documentary dedicated to her career, Sheryl Crow revisits her first tour bus, her three engagements, her zero marriages, and the time a lawyer told her not to bother with pursuing a sexual harassment claim against a music industry executive. She looks back at the time she was on the musical police procedural Cop Rock; she shows off her racks of amps and guitars; she discusses calling Bob Dylan for advice, impersonating his voice with a pinched “Ooh, that’s bad.” She even relays one of her first peeks into the bizarre world of superstardom, when she got to hang out with Michael Jackson and his pet chimpanzee Bubbles during her time as a backup vocalist on the Bad tour in the late 1980s.
Sheryl attempts to highlight the rise and long reach of the now-beloved singer-songwriter, and its many asides dutifully add up to a warm, flattering representation of a tremendously successful artist. The documentary makes strange work of Crow’s actual music career, however, squeezing her triumphs between anecdotes where she’s forced to explain men’s bad behavior, failing to probe the more interesting emotional forces that animate Crow’s inner life. How is it that we hear about MJ jabbing Bubbles with a Bic pen—from two people, no less—but nothing about the whole first album that Crow scrapped because its production was too squeaky-clean? In its efforts to entertain audiences with tabloid gossip and bold names, Sheryl sometimes misses the bigger picture of a woman who worked hard to build her success on her own terms.
The documentary opens with a clip from a 2003 interview with 60 Minutes, where Crow bristled at being called “driven,” noting that’s often just a code word for being a bitch. From there, director Amy Scott, whose credits include work on a film about the beloved NYC indie record store Other Music, hits typical music-doc beats, with a few stylistic twists. Without sticking to a strictly chronological timeline, Sheryl follows Crow’s massive career back to her parents’ musicianship in Missouri—halfway through, Bernice and Wendell show up with the photo albums to talk about their daughter’s home life and youthful energy. Elsewhere, talking heads include luminaries like Jimmy Iovine, Joe Walsh, and Emmylou Harris alongside confidants like Crow’s longtime manager, Scooter Weintraub, who talk about their admiration for a songwriter so committed to her own creative vision. There’s an abundance of archival media that contrasts more personal material—shots of Crow’s dog hopping up into a hotel bed, Polaroids of the songwriter at work in a studio—with intrusions from the nosy celebrity press that followed her.
But as Crow and her associates chronicle her ascent, another subject pushes to the forefront: the men in her orbit whose lives threatened to impede her artistic efforts. Explaining her big break as a backing vocalist for Michael Jackson, Crow peels off into an aside about the children around him, saying that she was unaware of any malfeasance at the time. It feels like a weird attempt to pre-empt any criticism of Crow’s connection to the troubled pop icon. The section segues into another one about Jackson’s then-manager, Frank DiLeo, who Crow says attempted to leverage his professional power with unspecified sexual harrassment.
Arriving at Crow’s 1993 debut album Tuesday Night Music Club, Sheryl digs into a controversy around Crow performing “Leaving Las Vegas” on The Late Show with David Letterman. In a post-performance interview, Letterman asked if the song was autobiographical; Crow said yes. The exchange supposedly upset John O’Brien, author of the 1990 novel (and eventual 1995 film) Leaving Las Vegas, which had served as inspiration for David Baerwald, one of Crow’s songwriting partners on the record. In Sheryl, Crow alleges that, unbeknownst to her, Baerwald had also promised songwriting royalties to O’Brien. When O’Brien died by suicide less than a month after Letterman, Crow ended up with a lion’s share of the blame, which was compounded when Baerwald wrote a letter to LA Weekly exorciating her over the incident. Though the dust-up is a focal point of the documentary—one shot rests on Crow breaking down in tears—Scott fails to note that O’Brien’s father and sister both explicitly absolved Crow, and continued to do so in following years, an omission that feels both careless to the audience and cruel to Crow.
For all the space that men take up in the story of Sheryl—embittered band mates, a disagreeable producer, an athletically dishonest ex-fiancé—Crow’s female relationships often feel under-examined. When these friends do show up, though, they provide invaluable insight into how Crow’s values influence her artistry. Laura Dern is an ebullient sunbeam as she gushes about her friendship with Crow, with whom she even lived for a while, after both were already established celebrities. Recording engineer Trina Shoemaker, whom Crow met when she went to complete her self-titled album at Daniel Lanois’ Kingsway Studios, is an especially compelling presence. She’s tough, she’s sharp, and she hit it off so well with Crow that the singer recruited Shoemaker to engineer 1998’s The Globe Sessions.
Shoemaker offers keen observations about how the institution of celebrity—“a machine that gets hungry,” as she puts it—creates demands that are at odds with Crow’s artistic perfectionism, but Scott quickly moves onto the next subject, ceding ground to stories about other men. The villains in Crow’s story feel like a parade of near-interchangeable music industry assholes, none of whom saw the talented, empathetic workhorse that Dern, Shoemaker, and several others got to know. The assholes may make for a convenient explanation about the challenges that women in music face—an exhausted narrative that the documentary nonetheless indulges—but every minute spent lingering on their actions pulls away from the woman we’re here to learn about.
In its final minutes, Sheryl shows Crow talking about her adopted sons, and her decision to be a solo parent rather than wait for a partner to make it happen. The home-video clips are charming and tender, but Scott’s extended sequence begins to feel like sentimental filler in a film that already lacks analytical bite. It likewise neglects the creative “mothering” that Crow did over her career, which becomes obvious as she expresses awe at having a 2018 Bonnaroo crowd belt “If It Makes You Happy” back at her. Though Crow speaks about her songs carrying over to a new generation, there’s no input from the younger women for whom her work was formative, such as Phoebe Bridgers, Olivia Rodrigo, or HAIM. Considering Scott’s general adherence to a boilerplate documentary format, it feels like a missed opportunity not to follow through with a couple of twentysomethings affirming her influence, completing the argument for Crow’s enduring artistic legacy.
Early in the documentary, Crow reflects on one challenge of sitting down for such a project. “It’s always hard to look back and talk about who you were, it’s only who you think you were,” she observes. No matter who she thinks she is, Crow’s fierce spirit is evident through the meaningful praise that some of Sheryl’s subjects offer; that spirit is how she created more room behind her, for other singers who wanted to cut loose with their feelings and have control over their creative output. But Sheryl is too often about the surface-level, tabloid version of Sheryl Crow rather than the fuller, more complex person who captured two generations’ worth of women’s disaffection. The movie adores her—who doesn’t?—but has a hard time showing why, even if you stripped away all of that goodwill, you’d still find an artist worth celebrating.
