In the music world, it’s pretty much a given that the mellower the artist, the more troubled he or she may be — think of the demons lurking behind those all those languid guitar strums or yacht-rock tempos. (See: the Doobie Brothers.) And thanks to the new documentary Sheryl, which premieres on Showtime May 6th, we can now add another name to that list: Sheryl Crow.
As we approach next year’s 30th anniversary of Tuesday Night Music Club, the album that made her a star after several false starts, Crow’s impact seems strangely undervalued. In addition to interviews with the singer and superstar pals ranging from Joe Walsh and Keith Richards to Brandi Carlile and Jason Isbell, Sheryl includes recreations of a young Crow flipping through her LP collection, pausing over albums by heroes like James Taylor and Fleetwood Mac.
Crow was indeed an inheritor of the soft-rock vibe embodied by those acts. But back in the grunge-focused Nineties, she also proudly kept alive the AOR FM-rock tradition of artists like, say, Tom Petty — and the fact that a woman was leading that charge, at that point in time, was momentous. A few years back, opening for the briefly reunited Hootie and the Blowfish at a show in South Carolina, Crow played a vigorous set of those radio hits: ”If It Makes You Happy,” “A Change Will Do You Good,” “My Favorite Mistake,” “Every Day Is a Winding Road.” But the mere fact that she was opening for them — a band whose moment faded pretty quickly — spoke to the way in which Crow is still taken for granted.
Fittingly, Sheryl explores the way that Crow’s road was not only winding but also relentlessly turbulent. More than just another one of those authorized-infomercial music docs that are all too prevalent these days, Sheryl (directed by Amy Scott) transforms into an examination of what it took to make it in music, especially for a woman in the pre-#MeToo era. In Crow’s case, we also glean the psychological impact on those who not only triumph but have to keep going year after year, album after album, tour after tour, broken engagement after broken engagement (three total, as she confesses).
Working its way through her life in conventional chronological fashion, Sheryl starts with Crow as a Missouri elementary-school teacher and cover-band singer, where she winds up engaged to a born-again band member. (In photos from that period of her life, she really does resemble someone you’d see at a Christian music concert.) Before long, she’s left her fiancé and that life behind and headed to L.A. Desperate to make any connections she can, she loses her job as a waitress when she hands her demo tape to a music-biz customer (despite being warned by her bosses not to do such a thing). Luckily, that ballsy move leads to backup-singer gigs (Johnny Mathis — who knew?) and a guest spot on Cop Rock, the still hard-to-fathom police series set to music. Even seeing a clip of it, with Crow singing and sashaying in a police station before grabbing a prop gun, boggles the mind.
Crow’s biggest early break arrives when she auditions for, and lands, a gig as one of Michael Jackson’s backup singers on his Bad tour in 1987. She and her early champion and manager, Scooter Weintraub, recall hanging with Jackson in a hotel room as he watches movies and TV shows (like Amos ‘n’ Andy) and plays with Bubbles the chimp. But looking back, Crow admits it was “so weird that he had a couple of little boys on the road with him at different times.” And thanks to her onstage duet with him on “I Just Can’t Stop Loving You,” tabloids suddenly announced that the two were lovers, which they weren’t. (With a muted eye roll, Crow suggest his handlers leaked the story.) Things only get more complicated when she alleges that Jackson’s manager, the late Frank DiLeo, was “all over me,” accusing him of sexual harassment and leading her to sink into “the darkest, most depressed place.”
Hooking up with a male-dominated gang of musicians and songwriters who dubbed their gatherings the Tuesday Night Music Club, Crow finds her crew and jettisons her Jackson-tour bouffant hair and wardrobe for an earthier image. Tuesday Night Music Club and its hits “All I Wanna Do” and “Leaving Las Vegas” finally land her the attention she’d been seeking. But even that comes with a stumble. Sheryl includes the notorious clip of David Letterman asking Crow on his show if “Leaving Las Vegas” was autobiographical. Despite having written the song with four other writers and using a title borrowed from a novel, Crow said yes, much to her later regret. Some of her collaborators, as well as the novelist, John O’Brien, took offense; O’Brien, who was apparently troubled and an alcoholic, eventually committed suicide by gunshot. Crow’s remark wasn’t the cause, but the backlash against her was intense, and recalling it here, she cries on camera.
Crow and her career recover, thanks in part to her winning lots of Grammys for that album and acknowledging her colleagues during that ceremony. There may be no more peak-Nineties moment than watching co-presenters Adam Sandler and Liz Phair announce her as the winner in one of those categories. Yet for every conquest — like helming her second album herself after co-producer Bill Bottrell bails after the first day of work, or participating in the groundbreaking initial Lilith Fair tour — there’s a comparable low.
Walmart bans her Sheryl Crow album over its anti-gun song, and later, she winds up in a relationship with Lance Armstrong. (Other celebrity relationships, with the likes of Eric Clapton and Owen Wilson, aren’t mentioned.) When the news of his doping comes out, much to her surprise, she recalls a “giant blowup” followed by him giving her a “five- or six-carat diamond.” But the damage to their relationship was done. (To ram the point home a little too heavy-handedly, the “lie to me” line from the “Strong Enough” video is seen.) And, of course, Crow was diagnosed with breast cancer only a few weeks after her breakup with Armstrong.
Sheryl also has its moments of levity. We get to hear the McDonald’s commercial on which she sang during her anything-for-a-gig years, and hear about the time she called Bob Dylan for advice on writer’s block. When she asked if he’d experienced it, she says he replied, “No, never have!” But even as she became what she now wryly calls a “legacy artist,” life never appeared in settle into the same relaxed grooves of her later music. Crow admits she probably wasn’t always the easiest person to work with, thanks to regular bouts of depression mentioned throughout the doc. “I’ve always had real high highs and real low lows,” she says at one point, “and that’s part of who I am.” Sounding as if he’s been there and back, a chilled-out Weintraub says of those periods, “It will pass.”
Given how successful Crow has been, it’s hard to call Sheryl any sort of cautionary tale; Keith Richards attests to her inner toughness, and he’s surely a good judge of that. The doc doesn’t demand sympathy for her as much as it communicates a shit-happens-and-you-roll-with-it philosophy. The future-looks-bright finale chronicles the making of her 2019 album Threads, recorded in her new, comfy home studio above her very own horse stable. Many of her days have been winding roads, but she at least seems ready to face whatever lies around the next bend.