Toward the end of Sheryl, a new documentary that’s somewhere between a gentle hagiography and an electronic press kit, Sheryl Crow reckons with her status as a music business veteran: “There’s a weird thing that happens when you become a ‘legacy artist.’ It’s sort of a sideways compliment. It’s like, ‘OK, you’ve stood the test of time but also you’re old and you just haven’t gone away.’” The accompanying double-album soundtrack, Sheryl: Music From the Feature Documentary, proves Crow’s point by balancing the core of her catalog—the songs that have stood the test the time—with the music she’s made as a legacy artist who no longer visits the upper reaches of the Billboard Hot 100. Partly a greatest hits collection, partly a testimonial to Crow’s endurance, Sheryl: Music From the Feature Documentary leans heavily into the bookends of her career, emphasizing her 1990s hits along with Threads, the 2019 album she claims is her farewell.
Like the film, Sheryl places the spotlight squarely on the music she made at the outset of her career, which seemed like a throwback even in the 1990s. Raised on classic rock, Crow tapped into a distinctly 1970s vibe with her 1993 debut Tuesday Night Music Club, a record steeped in the slick, heady sounds of Southern California. Its retro vibe was roughly in the same ballpark as alternative rock, which happened to crash into the mainstream just prior to the album’s release. Crow courted the alternative rock audience just once: She smudged up her sound on her self-titled second album, which arrived during alt-rock’s commercial peak in 1996. The thick, churning guitars of “If It Makes You Happy” represented a definitive break from the effervescent sunniness of “All I Wanna Do,” signifying her artistic independence more than any desire to chase trends.
Sheryl doesn’t create a strong differentiation between the sunny vibes of Tuesday Night Music Club and the relatively grungier aspects of Sheryl Crow. The soundtrack deliberately alternates material from the two records, a sequence that emphasizes continuity over evolution: What stands out is how Crow managed to freshen classic rock conventions without repudiating their clichés. Her best work demonstrated a clear debt to idols like Fleetwood Mac and the Rolling Stones—both Stevie Nicks and Keith Richards return the favor by appearing in Sheryl— but she synthesized these elements into a distinctive voice that sounded weathered, soulful, and hopeful. She deepened this approach on 1998’s The Globe Sessions, then turned it into shiny pop for C’mon C’mon in 2002.
