RS500 #475: Sheryl Crow — Sheryl Crow

The RS500 Project
3 min readDec 31, 2020
Cover of Sheryl Crow’s self-titled album

Year Released: 1996

Have I Heard This Before: I have never listened to a Sheryl Crow album in full before now. However, I was alive in the 1990s and I do have a mom, so I have more than a passing familiarity with Crow’s career as a whole. I do know that this has a few songs that I’m familiar with, and I’m so happy that “Soak Up The Sun” isn’t on this one.

High Points: But what I’m really happy about is that this has Sheryl Crow’s best-ever song on it. She’s had her fair share of radio hits, but “If It Makes You Happy” is absolutely her commercial and artistic peak. The album showcases her devotion to the traditions of classic rock, but this song is the moment where she makes those traditions her own. It’s the one moment on Sheryl Crow where her traditional side, her commercial instincts, and her authentic self coalesce into something truly great.

Low Points: It’s just a shame that the rest of Sheryl Crow is…fine. It’s okay, even kind of good. There’s definitely some crap here, though. Pretty much the second half of the album is dross, particularly the three indistinguishable ballads that close things out. And while “Every Day Is A Winding Road” isn’t Crow’s worst single, I still don’t like it very much. But even the better album tracks are dragged down by the MOR arrangements and production, indicating that Crow and her collaborators hoped that her lyrics would carry these songs. However, as far as her lyrics go, Crow is pretty unremarkable unless she’s trying too hard. “Maybe Angels” probably bears the worst of it in terms of how Crow often relies on stream-of-consciousness pop-culture references (something that would become a crutch for her later), but “Redemption Day” is probably the most dated piece here. Its half-hearted pleas to people in power to care are a relic of the politically-disengaged 1990s, a paean to action that doesn’t necessarily ask anyone to do anything aside from feeling bad.

Loose Thoughts: After listening to this, if I had to compare Sheryl Crow to anyone, it’d be Lenny Kravitz. Not only did they come up at around the same time, they’re also immensely talented performers who are held back by slavish adherence to the traditions and anachronisms of classic rock. Crow definitely doesn’t go for the “rock star” image that Kravitz used to cultivate, but it’s clear that her frame of reference for songwriting doesn’t go past the mid-1970s.

This is the first instance on the new list of the re-appraisal of the mini-boom of women singer-songwriters from the ’90s. Crow is perhaps the least interesting and most commercially viable from that era (though not the most commercially successful; that album will come much later). I’m not surprised at her inclusion, but I am surprised that it’s so low, given how many old rock dudes voted and how this is kind of an album tailor-made for them.

Rating: This is, unfortunately, a pretty Meh album in my book, despite the presence of a truly Great song. I gave it an honest shot, but if this is the high point of Sheryl Crow’s oeuvre, it’s safe to say that she’s not for me.

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The RS500 Project

A somewhat exhaustive run-through of Rolling Stone’s updated 500 Greatest Albums of All Time list to see if they’re all truly great.